Outlook Mail connector

connectors/outlook-mail/LICENSE

@@ -0,0 +1,21 @@
+MIT License
+
+Copyright (c) 2026 Plot Technologies Inc.
+
+Permission is hereby granted, free of charge, to any person obtaining a copy
+of this software and associated documentation files (the "Software"), to deal
+in the Software without restriction, including without limitation the rights
+to use, copy, modify, merge, publish, distribute, sublicense, and/or sell
+copies of the Software, and to permit persons to whom the Software is
+furnished to do so, subject to the following conditions:
+
+The above copyright notice and this permission notice shall be included in all
+copies or substantial portions of the Software.
+
+THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF ANY KIND, EXPRESS OR
+IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF MERCHANTABILITY,
+FITNESS FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT SHALL THE
+AUTHORS OR COPYRIGHT HOLDERS BE LIABLE FOR ANY CLAIM, DAMAGES OR OTHER
+LIABILITY, WHETHER IN AN ACTION OF CONTRACT, TORT OR OTHERWISE, ARISING FROM,
+OUT OF OR IN CONNECTION WITH THE SOFTWARE OR THE USE OR OTHER DEALINGS IN THE
+SOFTWARE.

connectors/outlook-mail/README.md

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+# Outlook Mail Connector
+
+Syncs Microsoft Outlook mail (personal outlook.com and work/school Microsoft 365
+accounts) into Plot via Microsoft Graph. Each Outlook conversation becomes a
+Plot thread; each message becomes a note on that thread.
+
+## What it syncs
+
+- **Channels** are mail folders (`/me/mailFolders`). Inbox and Sent Items are
+ enabled by default; Junk, Deleted Items, Drafts, Outbox, and Conversation
+ History are never offered. Enabling a folder backfills its history;
+ incremental changes are mailbox-wide (one Graph change-notification
+ subscription on `/me/messages`) and routed to whichever enabled folder the
+ conversation lives in.
+- **Notes** are keyed on `internetMessageId`, so folder moves and the echo of
+ mail sent from Plot dedupe cleanly. Drafts are skipped (Outlook autosave
+ would churn notes).
+- **Attachments** sync as file references and download on demand. Inline
+ images are skipped.
+- **Facets** for Plot's classifier come from RFC 5322 headers (List-Id,
+ Precedence, Auto-Submitted, …) plus Outlook's Focused Inbox
+ (`inferenceClassification`).
+
+## Two-way sync
+
+| Plot action | Outlook effect |
+|---|---|
+| Mark thread read / unread | `isRead` PATCHed on the conversation's messages (unread marks the latest message, read clears all) |
+| Add / remove To Do | `flag.flagStatus` set to `flagged` on the latest message / cleared on all flagged messages |
+| Reply on a thread | Graph `createReply` draft, recipients constrained by the note's access contacts, then sent |
+| New email thread | Graph draft + send, To/CC/BCC from the compose roster |
+
+Outlook-side changes flow back the other way: reading, flagging, replying, and
+new mail all arrive via change notifications (with a 60-minute delta-query
+self-heal catching anything push delivery misses).
+
+## OAuth scopes
+
+| Scope | Why |
+|---|---|
+| `Mail.ReadWrite` | Read folders/messages, update read + flag state, create drafts |
+| `Mail.Send` | Send replies and new mail composed in Plot |
+| `People.Read` | Resolve display names for frequent correspondents who aren't saved contacts |
+| `Contacts.Read` | Resolve display names from saved contacts |
+
+## Known limitations
+
+- **Avatars are not enriched.** Microsoft Graph photo endpoints return
+ auth-gated binary data with no public URL, so there is nothing to store in
+ `contact.avatar`. Contact *names* are enriched from People/Contacts; avatars
+ fall back to Gravatar on the client.
+- **Personal accounts degrade gracefully.** The People API returns limited
+ data for consumer accounts and may 403; enrichment is best-effort per
+ address. Focused Inbox signals are used only when present.
+- Reply bodies are sent as plain text without the quoted-history block (Plot
+ threads already carry the history as notes) — same behavior as the Gmail
+ connector.
+
+## Manual E2E test plan
+
+Prerequisites: the Azure app registration (see `docs/outlook.md` in the core
+repo) must include the delegated scopes `Mail.ReadWrite`, `Mail.Send`,
+`People.Read`, `Contacts.Read`; `AUTH_MICROSOFT_ID`/`AUTH_MICROSOFT_SECRET`
+set in `workers/api/.dev.vars`; tunnel running (`pnpm tunnel:start`) so Graph
+can reach the webhook endpoint (subscriptions are skipped on localhost).
+
+Run the pass twice: once with a **personal** (outlook.com) account and once
+with a **work/school** (Microsoft 365) account.
+
+1. **Connect + channels** — add an Outlook Mail connection; verify the folder
+ list excludes Junk/Deleted/Drafts and defaults Inbox + Sent Items on.
+2. **Backfill** — enable Inbox; verify threads appear with correct titles,
+ per-message notes, participants, timestamps, and that the "Syncing…" badge
+ clears. No unread badges from backfilled mail.
+3. **Inbound incremental** — send mail to the account from outside; verify the
+ thread appears (or extends) within seconds via the subscription.
+4. **Unread round-trip** — read a thread in Plot → message marked read in
+ Outlook; mark a thread unread in Outlook → unread in Plot. Verify no
+ echo loop (state settles after one hop each way).
+5. **Flag ↔ To Do round-trip** — flag in Outlook → thread becomes a Plot
+ To Do; toggle To Do off in Plot → flag cleared in Outlook.
+6. **Reply from Plot** — reply on a synced thread; verify recipients (To/Cc),
+ threading in Outlook, and that the sent message does NOT duplicate as a
+ new note when it syncs back.
+7. **Reply with attachment** — attach a small (<3 MB) and a large (>3 MB)
+ file; verify both arrive in Outlook.
+8. **Compose from Plot** — new email thread to a typed address + a contact
+ with CC; verify delivery, BCC kept out of visible headers, and the
+ originating note binds to the sent message.
+9. **Attachment download** — open a synced message's attachment in Plot.
+10. **Contact names** — verify senders not in the address book still resolve
+ display names where People data exists (work tenant), and degrade to
+ email-only on personal accounts.
+11. **Self-heal** — stop the tunnel for >1 hour, send external mail, restart;
+ verify the hourly delta sweep ingests the missed mail and the
+ subscription is renewed (check `selfHealCheck` log lines).
+12. **Teardown** — disable all folders; verify the Graph subscription is
+ deleted (no further webhook traffic) and re-enabling rebuilds it.

connectors/outlook-mail/package.json

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+{
+ "name": "@plotday/connector-outlook-mail",
+ "plotTwistId": "6c3773dd-e820-4043-a5bc-f4e299ca1a19",
+ "displayName": "Outlook Mail",
+ "description": "Send and reply to Outlook email, tracking threads for follow-up and snoozing the rest.",
+ "category": "messaging",
+ "logoUrl": "https://api.iconify.design/simple-icons/microsoftoutlook.svg",
+ "publisher": "Plot",
+ "publisherUrl": "https://plot.day",
+ "author": "Plot <team@plot.day> (https://plot.day)",
+ "license": "MIT",
+ "version": "0.1.0",
+ "type": "module",
+ "main": "./dist/index.js",
+ "types": "./dist/index.d.ts",
+ "exports": {
+ ".": {
+ "@plotday/connector": "./src/index.ts",
+ "types": "./dist/index.d.ts",
+ "default": "./dist/index.js"
+ }
+ },
+ "private": true,
+ "scripts": {
+ "build": "tsc",
+ "clean": "rm -rf dist",
+ "deploy": "plot deploy",
+ "lint": "plot lint",
+ "test": "vitest run",
+ "test:watch": "vitest"
+ },
+ "dependencies": {
+ "@plotday/email-classifier": "workspace:^",
+ "@plotday/twister": "workspace:^"
+ },
+ "devDependencies": {
+ "typescript": "^5.9.3",
+ "vitest": "^2.1.8"
+ },
+ "repository": {
+ "type": "git",
+ "url": "https://github.com/plotday/plot.git",
+ "directory": "connectors/outlook-mail"
+ },
+ "homepage": "https://plot.day",
+ "bugs": { "url": "https://github.com/plotday/plot/issues" },
+ "keywords": ["plot", "connector", "outlook", "microsoft", "email", "messaging"]
+}

connectors/outlook-mail/src/email-parsing.test.ts

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+import { describe, expect, it } from "vitest";
+import { stripQuotedReply } from "./email-parsing";
+
+describe("stripQuotedReply", () => {
+ it("cuts Outlook appendonsend reply chains", () => {
+ const html = `<div>New content</div><div id="appendonsend"></div><div>From: A<br>Sent: B<br>To: C<br>Subject: D</div>`;
+ expect(stripQuotedReply(html, "html")).toBe("<div>New content</div>");
+ });
+
+ it("cuts gmail_quote blocks from cross-client replies", () => {
+ const html = `<p>Reply</p><div class="gmail_quote">old</div>`;
+ expect(stripQuotedReply(html, "html")).toBe("<p>Reply</p>");
+ });
+
+ it("preserves forwarded messages", () => {
+ const text = "FYI\n---------- Forwarded message ---------\nFrom: x";
+ expect(stripQuotedReply(text, "text")).toBe(text);
+ });
+
+ it("cuts plain-text 'On ... wrote:' quotes", () => {
+ const text = "Thanks!\nOn Tue, Jun 10, 2026, Kris wrote:\n> earlier";
+ expect(stripQuotedReply(text, "text")).toBe("Thanks!");
+ });
+});

connectors/outlook-mail/src/email-parsing.ts

@@ -0,0 +1,153 @@
+// Quote-stripping helpers shared with the Gmail connector (copied from
+// gmail/src/gmail-api.ts — keep in sync).
+
+/**
+ * Locates the start of an Outlook-style "From: / Sent: / To: / Subject:"
+ * reply header even when the field labels are not wrapped in `<b>` or
+ * `<strong>` — e.g. corporate Exchange / Outlook variants that put the
+ * label in a `<span style="font-weight:bold">`, a `<font>` tag, or a
+ * plain `MsoNormal` paragraph with no inline bold at all.
+ *
+ * Strategy: replace every HTML tag with a same-length run of spaces so
+ * character offsets in the stripped text still map 1:1 back to the
+ * original. Then require each label to start at a structural boundary
+ * (start of string, a real newline, or 3+ whitespace chars — the smallest
+ * gap any HTML block tag produces when replaced). That anchor is what
+ * keeps user-written prose from false-matching.
+ *
+ * Returns the index of "From:" in the original content, or -1 if no
+ * Outlook reply header is found.
+ */
+export function findOutlookHeaderTagAgnostic(content: string): number {
+ const flat = content.replace(/<[^>]*>/g, (m) => " ".repeat(m.length));
+ const re =
+ /(?<=^|\n|[ \t]{3,})From:[\s\S]{0,1500}?(?<=\n|[ \t]{3,})Sent:[\s\S]{0,800}?(?<=\n|[ \t]{3,})To:[\s\S]{0,1500}?(?<=\n|[ \t]{3,})Subject:/i;
+ const m = flat.match(re);
+ return m?.index ?? -1;
+}
+
+/**
+ * Strips quoted reply content from an email body.
+ * Since Plot shows each message as a separate note in a thread,
+ * the quoted previous messages are redundant noise.
+ */
+export function stripQuotedReply(
+ content: string,
+ contentType: "text" | "html"
+): string {
+ if (!content) return content;
+
+ // Forwarded messages: the forwarded email IS the content the user wants to
+ // read. Gmail/Apple Mail wrap a forward in the same quote container Gmail uses
+ // for reply quotes, so the reply-stripping below would delete the whole body
+ // and leave an empty note. Keep the content as-is when it's a forward whose
+ // marker precedes any reply boundary.
+ if (isForwardedMessage(content)) return content;
+
+ if (contentType === "html") {
+ // Gmail wraps quoted replies in <div class="gmail_quote">
+ // Remove it and everything after it
+ const gmailQuoteIdx = content.search(
+ /<div[^>]*class\s*=\s*["'][^"']*gmail_quote[^"']*["'][^>]*>/i
+ );
+ if (gmailQuoteIdx !== -1) {
+ return content.substring(0, gmailQuoteIdx).trim();
+ }
+
+ // Some clients use <blockquote> with gmail_quote class
+ const blockquoteIdx = content.search(
+ /<blockquote[^>]*class\s*=\s*["'][^"']*gmail_quote[^"']*["'][^>]*>/i
+ );
+ if (blockquoteIdx !== -1) {
+ return content.substring(0, blockquoteIdx).trim();
+ }
+
+ // Microsoft Outlook-style: <div id="appendonsend"></div> followed by quoted content,
+ // or a <hr> divider followed by "From:" header pattern
+ const outlookDivIdx = content.search(
+ /<div[^>]*id\s*=\s*["'](?:appendonsend|divRplyFwdMsg)["'][^>]*>/i
+ );
+ if (outlookDivIdx !== -1) {
+ return content.substring(0, outlookDivIdx).trim();
+ }
+
+ // Outlook (desktop, OWA, and corporate Exchange clients) wraps replies
+ // with a "From: / Sent: / To: / Subject:" header block. The markup
+ // varies — sometimes `<b>` or `<strong>`, sometimes `<span
+ // style="font-weight:bold">`, sometimes a `MsoNormal` paragraph with
+ // no inline bold at all (Gowling-style corporate Exchange). Try the
+ // tight bold-wrapped pattern first, then fall back to a tag-agnostic
+ // boundary match.
+ const outlookHeaderRe =
+ /<(b|strong)[^>]*>\s*From:?\s*<\/\1>[\s\S]{0,1000}<(b|strong)[^>]*>\s*Sent:?\s*<\/\2>[\s\S]{0,1000}<(b|strong)[^>]*>\s*To:?\s*<\/\3>[\s\S]{0,1000}<(b|strong)[^>]*>\s*Subject:?\s*<\/\4>/i;
+ const outlookHeaderMatch = content.match(outlookHeaderRe);
+ const fromIdx =
+ outlookHeaderMatch?.index ?? findOutlookHeaderTagAgnostic(content);
+ if (fromIdx !== -1) {
+ const lookbackStart = Math.max(0, fromIdx - 1000);
+ const lookback = content.substring(lookbackStart, fromIdx);
+ // Prefer the latest structural divider (border-top div or <hr>)
+ // before the From: tag — that's the user/quoted boundary in
+ // Outlook's standard reply format.
+ const dividerRe =
+ /<hr\b[^>]*>|<div[^>]*style\s*=\s*["'][^"']*border-top\s*:[^"']*["'][^>]*>/gi;
+ let lastDivider = -1;
+ let match: RegExpExecArray | null;
+ while ((match = dividerRe.exec(lookback)) !== null) {
+ lastDivider = match.index;
+ }
+ let cut = fromIdx;
+ if (lastDivider !== -1) {
+ cut = lookbackStart + lastDivider;
+ } else {
+ // No divider — cut at the start of the wrapping <p> or <div>.
+ const lastP = lookback.lastIndexOf("<p");
+ const lastDiv = lookback.lastIndexOf("<div");
+ const wrapper = Math.max(lastP, lastDiv);
+ if (wrapper !== -1) {
+ cut = lookbackStart + wrapper;
+ }
+ }
+ return content.substring(0, cut).trim();
+ }
+
+ return content;
+ }
+
+ // Plain text: look for "On ... wrote:" followed by quoted lines
+ const lines = content.split("\n");
+ for (let i = 0; i < lines.length; i++) {
+ const line = lines[i].trim();
+
+ // "On [date], [name] wrote:" or "On [date], [name] <email> wrote:"
+ if (/^On .+ wrote:\s*$/.test(line)) {
+ // Verify next non-empty line starts with ">" (actual quoted content)
+ const nextContentLine = lines.slice(i + 1).find((l) => l.trim() !== "");
+ if (nextContentLine && nextContentLine.trim().startsWith(">")) {
+ return lines
+ .slice(0, i)
+ .join("\n")
+ .trim();
+ }
+ }
+ }
+
+ return content;
+}
+
+/**
+ * Detects a forwarded message so {@link stripQuotedReply} can preserve it.
+ * Matches Gmail's dashed "---------- Forwarded message ---------" marker and
+ * Apple Mail's "Begin forwarded message:". Returns false when a reply boundary
+ * ("On … wrote:") precedes the forward marker — that's a reply quoting a
+ * forward, which the reply-stripper should still trim.
+ */
+function isForwardedMessage(content: string): boolean {
+ const fwdIdx = content.search(
+ /(-{2,}\s*Forwarded message\s*-{2,}|Begin forwarded message:)/i
+ );
+ if (fwdIdx === -1) return false;
+ const replyIdx = content.search(/On\s[\s\S]{0,200}?\swrote:/i);
+ if (replyIdx !== -1 && replyIdx < fwdIdx) return false;
+ return true;
+}

connectors/outlook-mail/LICENSE

@@ -0,0 +1,21 @@
+MIT License
+
+Copyright (c) 2026 Plot Technologies Inc.
+
+Permission is hereby granted, free of charge, to any person obtaining a copy
+of this software and associated documentation files (the "Software"), to deal
+in the Software without restriction, including without limitation the rights
+to use, copy, modify, merge, publish, distribute, sublicense, and/or sell
+copies of the Software, and to permit persons to whom the Software is
+furnished to do so, subject to the following conditions:
+
+The above copyright notice and this permission notice shall be included in all
+copies or substantial portions of the Software.
+
+THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF ANY KIND, EXPRESS OR
+IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF MERCHANTABILITY,
+FITNESS FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT SHALL THE
+AUTHORS OR COPYRIGHT HOLDERS BE LIABLE FOR ANY CLAIM, DAMAGES OR OTHER
+LIABILITY, WHETHER IN AN ACTION OF CONTRACT, TORT OR OTHERWISE, ARISING FROM,
+OUT OF OR IN CONNECTION WITH THE SOFTWARE OR THE USE OR OTHER DEALINGS IN THE
+SOFTWARE.

connectors/outlook-mail/README.md

@@ -0,0 +1,98 @@
+# Outlook Mail Connector
+
+Syncs Microsoft Outlook mail (personal outlook.com and work/school Microsoft 365
+accounts) into Plot via Microsoft Graph. Each Outlook conversation becomes a
+Plot thread; each message becomes a note on that thread.
+
+## What it syncs
+
+- **Channels** are mail folders (`/me/mailFolders`). Inbox and Sent Items are
+ enabled by default; Junk, Deleted Items, Drafts, Outbox, and Conversation
+ History are never offered. Enabling a folder backfills its history;
+ incremental changes are mailbox-wide (one Graph change-notification
+ subscription on `/me/messages`) and routed to whichever enabled folder the
+ conversation lives in.
+- **Notes** are keyed on `internetMessageId`, so folder moves and the echo of
+ mail sent from Plot dedupe cleanly. Drafts are skipped (Outlook autosave
+ would churn notes).
+- **Attachments** sync as file references and download on demand. Inline
+ images are skipped.
+- **Facets** for Plot's classifier come from RFC 5322 headers (List-Id,
+ Precedence, Auto-Submitted, …) plus Outlook's Focused Inbox
+ (`inferenceClassification`).
+
+## Two-way sync
+
+| Plot action | Outlook effect |
+|---|---|
+| Mark thread read / unread | `isRead` PATCHed on the conversation's messages (unread marks the latest message, read clears all) |
+| Add / remove To Do | `flag.flagStatus` set to `flagged` on the latest message / cleared on all flagged messages |
+| Reply on a thread | Graph `createReply` draft, recipients constrained by the note's access contacts, then sent |
+| New email thread | Graph draft + send, To/CC/BCC from the compose roster |
+
+Outlook-side changes flow back the other way: reading, flagging, replying, and
+new mail all arrive via change notifications (with a 60-minute delta-query
+self-heal catching anything push delivery misses).
+
+## OAuth scopes
+
+| Scope | Why |
+|---|---|
+| `Mail.ReadWrite` | Read folders/messages, update read + flag state, create drafts |
+| `Mail.Send` | Send replies and new mail composed in Plot |
+| `People.Read` | Resolve display names for frequent correspondents who aren't saved contacts |
+| `Contacts.Read` | Resolve display names from saved contacts |
+
+## Known limitations
+
+- **Avatars are not enriched.** Microsoft Graph photo endpoints return
+ auth-gated binary data with no public URL, so there is nothing to store in
+ `contact.avatar`. Contact *names* are enriched from People/Contacts; avatars
+ fall back to Gravatar on the client.
+- **Personal accounts degrade gracefully.** The People API returns limited
+ data for consumer accounts and may 403; enrichment is best-effort per
+ address. Focused Inbox signals are used only when present.
+- Reply bodies are sent as plain text without the quoted-history block (Plot
+ threads already carry the history as notes) — same behavior as the Gmail
+ connector.
+
+## Manual E2E test plan
+
+Prerequisites: the Azure app registration (see `docs/outlook.md` in the core
+repo) must include the delegated scopes `Mail.ReadWrite`, `Mail.Send`,
+`People.Read`, `Contacts.Read`; `AUTH_MICROSOFT_ID`/`AUTH_MICROSOFT_SECRET`
+set in `workers/api/.dev.vars`; tunnel running (`pnpm tunnel:start`) so Graph
+can reach the webhook endpoint (subscriptions are skipped on localhost).
+
+Run the pass twice: once with a **personal** (outlook.com) account and once
+with a **work/school** (Microsoft 365) account.
+
+1. **Connect + channels** — add an Outlook Mail connection; verify the folder
+ list excludes Junk/Deleted/Drafts and defaults Inbox + Sent Items on.
+2. **Backfill** — enable Inbox; verify threads appear with correct titles,
+ per-message notes, participants, timestamps, and that the "Syncing…" badge
+ clears. No unread badges from backfilled mail.
+3. **Inbound incremental** — send mail to the account from outside; verify the
+ thread appears (or extends) within seconds via the subscription.
+4. **Unread round-trip** — read a thread in Plot → message marked read in
+ Outlook; mark a thread unread in Outlook → unread in Plot. Verify no
+ echo loop (state settles after one hop each way).
+5. **Flag ↔ To Do round-trip** — flag in Outlook → thread becomes a Plot
+ To Do; toggle To Do off in Plot → flag cleared in Outlook.
+6. **Reply from Plot** — reply on a synced thread; verify recipients (To/Cc),
+ threading in Outlook, and that the sent message does NOT duplicate as a
+ new note when it syncs back.
+7. **Reply with attachment** — attach a small (<3 MB) and a large (>3 MB)
+ file; verify both arrive in Outlook.
+8. **Compose from Plot** — new email thread to a typed address + a contact
+ with CC; verify delivery, BCC kept out of visible headers, and the
+ originating note binds to the sent message.
+9. **Attachment download** — open a synced message's attachment in Plot.
+10. **Contact names** — verify senders not in the address book still resolve
+ display names where People data exists (work tenant), and degrade to
+ email-only on personal accounts.
+11. **Self-heal** — stop the tunnel for >1 hour, send external mail, restart;
+ verify the hourly delta sweep ingests the missed mail and the
+ subscription is renewed (check `selfHealCheck` log lines).
+12. **Teardown** — disable all folders; verify the Graph subscription is
+ deleted (no further webhook traffic) and re-enabling rebuilds it.

connectors/outlook-mail/package.json

@@ -0,0 +1,48 @@
+{
+ "name": "@plotday/connector-outlook-mail",
+ "plotTwistId": "6c3773dd-e820-4043-a5bc-f4e299ca1a19",
+ "displayName": "Outlook Mail",
+ "description": "Send and reply to Outlook email, tracking threads for follow-up and snoozing the rest.",
+ "category": "messaging",
+ "logoUrl": "https://api.iconify.design/simple-icons/microsoftoutlook.svg",
+ "publisher": "Plot",
+ "publisherUrl": "https://plot.day",
+ "author": "Plot <team@plot.day> (https://plot.day)",
+ "license": "MIT",
+ "version": "0.1.0",
+ "type": "module",
+ "main": "./dist/index.js",
+ "types": "./dist/index.d.ts",
+ "exports": {
+ ".": {
+ "@plotday/connector": "./src/index.ts",
+ "types": "./dist/index.d.ts",
+ "default": "./dist/index.js"
+ }
+ },
+ "private": true,
+ "scripts": {
+ "build": "tsc",
+ "clean": "rm -rf dist",
+ "deploy": "plot deploy",
+ "lint": "plot lint",
+ "test": "vitest run",
+ "test:watch": "vitest"
+ },
+ "dependencies": {
+ "@plotday/email-classifier": "workspace:^",
+ "@plotday/twister": "workspace:^"
+ },
+ "devDependencies": {
+ "typescript": "^5.9.3",
+ "vitest": "^2.1.8"
+ },
+ "repository": {
+ "type": "git",
+ "url": "https://github.com/plotday/plot.git",
+ "directory": "connectors/outlook-mail"
+ },
+ "homepage": "https://plot.day",
+ "bugs": { "url": "https://github.com/plotday/plot/issues" },
+ "keywords": ["plot", "connector", "outlook", "microsoft", "email", "messaging"]
+}

connectors/outlook-mail/src/email-parsing.test.ts

@@ -0,0 +1,24 @@
+import { describe, expect, it } from "vitest";
+import { stripQuotedReply } from "./email-parsing";
+
+describe("stripQuotedReply", () => {
+ it("cuts Outlook appendonsend reply chains", () => {
+ const html = `<div>New content</div><div id="appendonsend"></div><div>From: A<br>Sent: B<br>To: C<br>Subject: D</div>`;
+ expect(stripQuotedReply(html, "html")).toBe("<div>New content</div>");
+ });
+
+ it("cuts gmail_quote blocks from cross-client replies", () => {
+ const html = `<p>Reply</p><div class="gmail_quote">old</div>`;
+ expect(stripQuotedReply(html, "html")).toBe("<p>Reply</p>");
+ });
+
+ it("preserves forwarded messages", () => {
+ const text = "FYI\n---------- Forwarded message ---------\nFrom: x";
+ expect(stripQuotedReply(text, "text")).toBe(text);
+ });
+
+ it("cuts plain-text 'On ... wrote:' quotes", () => {
+ const text = "Thanks!\nOn Tue, Jun 10, 2026, Kris wrote:\n> earlier";
+ expect(stripQuotedReply(text, "text")).toBe("Thanks!");
+ });
+});

connectors/outlook-mail/src/email-parsing.ts

@@ -0,0 +1,153 @@
+// Quote-stripping helpers shared with the Gmail connector (copied from
+// gmail/src/gmail-api.ts — keep in sync).
+
+/**
+ * Locates the start of an Outlook-style "From: / Sent: / To: / Subject:"
+ * reply header even when the field labels are not wrapped in `<b>` or
+ * `<strong>` — e.g. corporate Exchange / Outlook variants that put the
+ * label in a `<span style="font-weight:bold">`, a `<font>` tag, or a
+ * plain `MsoNormal` paragraph with no inline bold at all.
+ *
+ * Strategy: replace every HTML tag with a same-length run of spaces so
+ * character offsets in the stripped text still map 1:1 back to the
+ * original. Then require each label to start at a structural boundary
+ * (start of string, a real newline, or 3+ whitespace chars — the smallest
+ * gap any HTML block tag produces when replaced). That anchor is what
+ * keeps user-written prose from false-matching.
+ *
+ * Returns the index of "From:" in the original content, or -1 if no
+ * Outlook reply header is found.
+ */
+export function findOutlookHeaderTagAgnostic(content: string): number {
+ const flat = content.replace(/<[^>]*>/g, (m) => " ".repeat(m.length));
+ const re =
+ /(?<=^|\n|[ \t]{3,})From:[\s\S]{0,1500}?(?<=\n|[ \t]{3,})Sent:[\s\S]{0,800}?(?<=\n|[ \t]{3,})To:[\s\S]{0,1500}?(?<=\n|[ \t]{3,})Subject:/i;
+ const m = flat.match(re);
+ return m?.index ?? -1;
+}
+
+/**
+ * Strips quoted reply content from an email body.
+ * Since Plot shows each message as a separate note in a thread,
+ * the quoted previous messages are redundant noise.
+ */
+export function stripQuotedReply(
+ content: string,
+ contentType: "text" | "html"
+): string {
+ if (!content) return content;
+
+ // Forwarded messages: the forwarded email IS the content the user wants to
+ // read. Gmail/Apple Mail wrap a forward in the same quote container Gmail uses
+ // for reply quotes, so the reply-stripping below would delete the whole body
+ // and leave an empty note. Keep the content as-is when it's a forward whose
+ // marker precedes any reply boundary.
+ if (isForwardedMessage(content)) return content;
+
+ if (contentType === "html") {
+ // Gmail wraps quoted replies in <div class="gmail_quote">
+ // Remove it and everything after it
+ const gmailQuoteIdx = content.search(
+ /<div[^>]*class\s*=\s*["'][^"']*gmail_quote[^"']*["'][^>]*>/i
+ );
+ if (gmailQuoteIdx !== -1) {
+ return content.substring(0, gmailQuoteIdx).trim();
+ }
+
+ // Some clients use <blockquote> with gmail_quote class
+ const blockquoteIdx = content.search(
+ /<blockquote[^>]*class\s*=\s*["'][^"']*gmail_quote[^"']*["'][^>]*>/i
+ );
+ if (blockquoteIdx !== -1) {
+ return content.substring(0, blockquoteIdx).trim();
+ }
+
+ // Microsoft Outlook-style: <div id="appendonsend"></div> followed by quoted content,
+ // or a <hr> divider followed by "From:" header pattern
+ const outlookDivIdx = content.search(
+ /<div[^>]*id\s*=\s*["'](?:appendonsend|divRplyFwdMsg)["'][^>]*>/i
+ );
+ if (outlookDivIdx !== -1) {
+ return content.substring(0, outlookDivIdx).trim();
+ }
+
+ // Outlook (desktop, OWA, and corporate Exchange clients) wraps replies
+ // with a "From: / Sent: / To: / Subject:" header block. The markup
+ // varies — sometimes `<b>` or `<strong>`, sometimes `<span
+ // style="font-weight:bold">`, sometimes a `MsoNormal` paragraph with
+ // no inline bold at all (Gowling-style corporate Exchange). Try the
+ // tight bold-wrapped pattern first, then fall back to a tag-agnostic
+ // boundary match.
+ const outlookHeaderRe =
+ /<(b|strong)[^>]*>\s*From:?\s*<\/\1>[\s\S]{0,1000}<(b|strong)[^>]*>\s*Sent:?\s*<\/\2>[\s\S]{0,1000}<(b|strong)[^>]*>\s*To:?\s*<\/\3>[\s\S]{0,1000}<(b|strong)[^>]*>\s*Subject:?\s*<\/\4>/i;
+ const outlookHeaderMatch = content.match(outlookHeaderRe);
+ const fromIdx =
+ outlookHeaderMatch?.index ?? findOutlookHeaderTagAgnostic(content);
+ if (fromIdx !== -1) {
+ const lookbackStart = Math.max(0, fromIdx - 1000);
+ const lookback = content.substring(lookbackStart, fromIdx);
+ // Prefer the latest structural divider (border-top div or <hr>)
+ // before the From: tag — that's the user/quoted boundary in
+ // Outlook's standard reply format.
+ const dividerRe =
+ /<hr\b[^>]*>|<div[^>]*style\s*=\s*["'][^"']*border-top\s*:[^"']*["'][^>]*>/gi;
+ let lastDivider = -1;
+ let match: RegExpExecArray | null;
+ while ((match = dividerRe.exec(lookback)) !== null) {
+ lastDivider = match.index;
+ }
+ let cut = fromIdx;
+ if (lastDivider !== -1) {
+ cut = lookbackStart + lastDivider;
+ } else {
+ // No divider — cut at the start of the wrapping <p> or <div>.
+ const lastP = lookback.lastIndexOf("<p");
+ const lastDiv = lookback.lastIndexOf("<div");
+ const wrapper = Math.max(lastP, lastDiv);
+ if (wrapper !== -1) {
+ cut = lookbackStart + wrapper;
+ }
+ }
+ return content.substring(0, cut).trim();
+ }
+
+ return content;
+ }
+
+ // Plain text: look for "On ... wrote:" followed by quoted lines
+ const lines = content.split("\n");
+ for (let i = 0; i < lines.length; i++) {
+ const line = lines[i].trim();
+
+ // "On [date], [name] wrote:" or "On [date], [name] <email> wrote:"
+ if (/^On .+ wrote:\s*$/.test(line)) {
+ // Verify next non-empty line starts with ">" (actual quoted content)
+ const nextContentLine = lines.slice(i + 1).find((l) => l.trim() !== "");
+ if (nextContentLine && nextContentLine.trim().startsWith(">")) {
+ return lines
+ .slice(0, i)
+ .join("\n")
+ .trim();
+ }
+ }
+ }
+
+ return content;
+}
+
+/**
+ * Detects a forwarded message so {@link stripQuotedReply} can preserve it.
+ * Matches Gmail's dashed "---------- Forwarded message ---------" marker and
+ * Apple Mail's "Begin forwarded message:". Returns false when a reply boundary
+ * ("On … wrote:") precedes the forward marker — that's a reply quoting a
+ * forward, which the reply-stripper should still trim.
+ */
+function isForwardedMessage(content: string): boolean {
+ const fwdIdx = content.search(
+ /(-{2,}\s*Forwarded message\s*-{2,}|Begin forwarded message:)/i
+ );
+ if (fwdIdx === -1) return false;
+ const replyIdx = content.search(/On\s[\s\S]{0,200}?\swrote:/i);
+ if (replyIdx !== -1 && replyIdx < fwdIdx) return false;
+ return true;
+}

connectors/outlook-mail/LICENSE

@@ -0,0 +1,21 @@
+MIT License
+
+Copyright (c) 2026 Plot Technologies Inc.
+
+Permission is hereby granted, free of charge, to any person obtaining a copy
+of this software and associated documentation files (the "Software"), to deal
+in the Software without restriction, including without limitation the rights
+to use, copy, modify, merge, publish, distribute, sublicense, and/or sell
+copies of the Software, and to permit persons to whom the Software is
+furnished to do so, subject to the following conditions:
+
+The above copyright notice and this permission notice shall be included in all
+copies or substantial portions of the Software.
+
+THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF ANY KIND, EXPRESS OR
+IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF MERCHANTABILITY,
+FITNESS FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT SHALL THE
+AUTHORS OR COPYRIGHT HOLDERS BE LIABLE FOR ANY CLAIM, DAMAGES OR OTHER
+LIABILITY, WHETHER IN AN ACTION OF CONTRACT, TORT OR OTHERWISE, ARISING FROM,
+OUT OF OR IN CONNECTION WITH THE SOFTWARE OR THE USE OR OTHER DEALINGS IN THE
+SOFTWARE.

connectors/outlook-mail/README.md

@@ -0,0 +1,98 @@
+# Outlook Mail Connector
+
+Syncs Microsoft Outlook mail (personal outlook.com and work/school Microsoft 365
+accounts) into Plot via Microsoft Graph. Each Outlook conversation becomes a
+Plot thread; each message becomes a note on that thread.
+
+## What it syncs
+
+- **Channels** are mail folders (`/me/mailFolders`). Inbox and Sent Items are
+ enabled by default; Junk, Deleted Items, Drafts, Outbox, and Conversation
+ History are never offered. Enabling a folder backfills its history;
+ incremental changes are mailbox-wide (one Graph change-notification
+ subscription on `/me/messages`) and routed to whichever enabled folder the
+ conversation lives in.
+- **Notes** are keyed on `internetMessageId`, so folder moves and the echo of
+ mail sent from Plot dedupe cleanly. Drafts are skipped (Outlook autosave
+ would churn notes).
+- **Attachments** sync as file references and download on demand. Inline
+ images are skipped.
+- **Facets** for Plot's classifier come from RFC 5322 headers (List-Id,
+ Precedence, Auto-Submitted, …) plus Outlook's Focused Inbox
+ (`inferenceClassification`).
+
+## Two-way sync
+
+| Plot action | Outlook effect |
+|---|---|
+| Mark thread read / unread | `isRead` PATCHed on the conversation's messages (unread marks the latest message, read clears all) |
+| Add / remove To Do | `flag.flagStatus` set to `flagged` on the latest message / cleared on all flagged messages |
+| Reply on a thread | Graph `createReply` draft, recipients constrained by the note's access contacts, then sent |
+| New email thread | Graph draft + send, To/CC/BCC from the compose roster |
+
+Outlook-side changes flow back the other way: reading, flagging, replying, and
+new mail all arrive via change notifications (with a 60-minute delta-query
+self-heal catching anything push delivery misses).
+
+## OAuth scopes
+
+| Scope | Why |
+|---|---|
+| `Mail.ReadWrite` | Read folders/messages, update read + flag state, create drafts |
+| `Mail.Send` | Send replies and new mail composed in Plot |
+| `People.Read` | Resolve display names for frequent correspondents who aren't saved contacts |
+| `Contacts.Read` | Resolve display names from saved contacts |
+
+## Known limitations
+
+- **Avatars are not enriched.** Microsoft Graph photo endpoints return
+ auth-gated binary data with no public URL, so there is nothing to store in
+ `contact.avatar`. Contact *names* are enriched from People/Contacts; avatars
+ fall back to Gravatar on the client.
+- **Personal accounts degrade gracefully.** The People API returns limited
+ data for consumer accounts and may 403; enrichment is best-effort per
+ address. Focused Inbox signals are used only when present.
+- Reply bodies are sent as plain text without the quoted-history block (Plot
+ threads already carry the history as notes) — same behavior as the Gmail
+ connector.
+
+## Manual E2E test plan
+
+Prerequisites: the Azure app registration (see `docs/outlook.md` in the core
+repo) must include the delegated scopes `Mail.ReadWrite`, `Mail.Send`,
+`People.Read`, `Contacts.Read`; `AUTH_MICROSOFT_ID`/`AUTH_MICROSOFT_SECRET`
+set in `workers/api/.dev.vars`; tunnel running (`pnpm tunnel:start`) so Graph
+can reach the webhook endpoint (subscriptions are skipped on localhost).
+
+Run the pass twice: once with a **personal** (outlook.com) account and once
+with a **work/school** (Microsoft 365) account.
+
+1. **Connect + channels** — add an Outlook Mail connection; verify the folder
+ list excludes Junk/Deleted/Drafts and defaults Inbox + Sent Items on.
+2. **Backfill** — enable Inbox; verify threads appear with correct titles,
+ per-message notes, participants, timestamps, and that the "Syncing…" badge
+ clears. No unread badges from backfilled mail.
+3. **Inbound incremental** — send mail to the account from outside; verify the
+ thread appears (or extends) within seconds via the subscription.
+4. **Unread round-trip** — read a thread in Plot → message marked read in
+ Outlook; mark a thread unread in Outlook → unread in Plot. Verify no
+ echo loop (state settles after one hop each way).
+5. **Flag ↔ To Do round-trip** — flag in Outlook → thread becomes a Plot
+ To Do; toggle To Do off in Plot → flag cleared in Outlook.
+6. **Reply from Plot** — reply on a synced thread; verify recipients (To/Cc),
+ threading in Outlook, and that the sent message does NOT duplicate as a
+ new note when it syncs back.
+7. **Reply with attachment** — attach a small (<3 MB) and a large (>3 MB)
+ file; verify both arrive in Outlook.
+8. **Compose from Plot** — new email thread to a typed address + a contact
+ with CC; verify delivery, BCC kept out of visible headers, and the
+ originating note binds to the sent message.
+9. **Attachment download** — open a synced message's attachment in Plot.
+10. **Contact names** — verify senders not in the address book still resolve
+ display names where People data exists (work tenant), and degrade to
+ email-only on personal accounts.
+11. **Self-heal** — stop the tunnel for >1 hour, send external mail, restart;
+ verify the hourly delta sweep ingests the missed mail and the
+ subscription is renewed (check `selfHealCheck` log lines).
+12. **Teardown** — disable all folders; verify the Graph subscription is
+ deleted (no further webhook traffic) and re-enabling rebuilds it.

connectors/outlook-mail/package.json

@@ -0,0 +1,48 @@
+{
+ "name": "@plotday/connector-outlook-mail",
+ "plotTwistId": "6c3773dd-e820-4043-a5bc-f4e299ca1a19",
+ "displayName": "Outlook Mail",
+ "description": "Send and reply to Outlook email, tracking threads for follow-up and snoozing the rest.",
+ "category": "messaging",
+ "logoUrl": "https://api.iconify.design/simple-icons/microsoftoutlook.svg",
+ "publisher": "Plot",
+ "publisherUrl": "https://plot.day",
+ "author": "Plot <team@plot.day> (https://plot.day)",
+ "license": "MIT",
+ "version": "0.1.0",
+ "type": "module",
+ "main": "./dist/index.js",
+ "types": "./dist/index.d.ts",
+ "exports": {
+ ".": {
+ "@plotday/connector": "./src/index.ts",
+ "types": "./dist/index.d.ts",
+ "default": "./dist/index.js"
+ }
+ },
+ "private": true,
+ "scripts": {
+ "build": "tsc",
+ "clean": "rm -rf dist",
+ "deploy": "plot deploy",
+ "lint": "plot lint",
+ "test": "vitest run",
+ "test:watch": "vitest"
+ },
+ "dependencies": {
+ "@plotday/email-classifier": "workspace:^",
+ "@plotday/twister": "workspace:^"
+ },
+ "devDependencies": {
+ "typescript": "^5.9.3",
+ "vitest": "^2.1.8"
+ },
+ "repository": {
+ "type": "git",
+ "url": "https://github.com/plotday/plot.git",
+ "directory": "connectors/outlook-mail"
+ },
+ "homepage": "https://plot.day",
+ "bugs": { "url": "https://github.com/plotday/plot/issues" },
+ "keywords": ["plot", "connector", "outlook", "microsoft", "email", "messaging"]
+}

connectors/outlook-mail/src/email-parsing.test.ts

@@ -0,0 +1,24 @@
+import { describe, expect, it } from "vitest";
+import { stripQuotedReply } from "./email-parsing";
+
+describe("stripQuotedReply", () => {
+ it("cuts Outlook appendonsend reply chains", () => {
+ const html = `<div>New content</div><div id="appendonsend"></div><div>From: A<br>Sent: B<br>To: C<br>Subject: D</div>`;
+ expect(stripQuotedReply(html, "html")).toBe("<div>New content</div>");
+ });
+
+ it("cuts gmail_quote blocks from cross-client replies", () => {
+ const html = `<p>Reply</p><div class="gmail_quote">old</div>`;
+ expect(stripQuotedReply(html, "html")).toBe("<p>Reply</p>");
+ });
+
+ it("preserves forwarded messages", () => {
+ const text = "FYI\n---------- Forwarded message ---------\nFrom: x";
+ expect(stripQuotedReply(text, "text")).toBe(text);
+ });
+
+ it("cuts plain-text 'On ... wrote:' quotes", () => {
+ const text = "Thanks!\nOn Tue, Jun 10, 2026, Kris wrote:\n> earlier";
+ expect(stripQuotedReply(text, "text")).toBe("Thanks!");
+ });
+});

connectors/outlook-mail/src/email-parsing.ts

@@ -0,0 +1,153 @@
+// Quote-stripping helpers shared with the Gmail connector (copied from
+// gmail/src/gmail-api.ts — keep in sync).
+
+/**
+ * Locates the start of an Outlook-style "From: / Sent: / To: / Subject:"
+ * reply header even when the field labels are not wrapped in `<b>` or
+ * `<strong>` — e.g. corporate Exchange / Outlook variants that put the
+ * label in a `<span style="font-weight:bold">`, a `<font>` tag, or a
+ * plain `MsoNormal` paragraph with no inline bold at all.
+ *
+ * Strategy: replace every HTML tag with a same-length run of spaces so
+ * character offsets in the stripped text still map 1:1 back to the
+ * original. Then require each label to start at a structural boundary
+ * (start of string, a real newline, or 3+ whitespace chars — the smallest
+ * gap any HTML block tag produces when replaced). That anchor is what
+ * keeps user-written prose from false-matching.
+ *
+ * Returns the index of "From:" in the original content, or -1 if no
+ * Outlook reply header is found.
+ */
+export function findOutlookHeaderTagAgnostic(content: string): number {
+ const flat = content.replace(/<[^>]*>/g, (m) => " ".repeat(m.length));
+ const re =
+ /(?<=^|\n|[ \t]{3,})From:[\s\S]{0,1500}?(?<=\n|[ \t]{3,})Sent:[\s\S]{0,800}?(?<=\n|[ \t]{3,})To:[\s\S]{0,1500}?(?<=\n|[ \t]{3,})Subject:/i;
+ const m = flat.match(re);
+ return m?.index ?? -1;
+}
+
+/**
+ * Strips quoted reply content from an email body.
+ * Since Plot shows each message as a separate note in a thread,
+ * the quoted previous messages are redundant noise.
+ */
+export function stripQuotedReply(
+ content: string,
+ contentType: "text" | "html"
+): string {
+ if (!content) return content;
+
+ // Forwarded messages: the forwarded email IS the content the user wants to
+ // read. Gmail/Apple Mail wrap a forward in the same quote container Gmail uses
+ // for reply quotes, so the reply-stripping below would delete the whole body
+ // and leave an empty note. Keep the content as-is when it's a forward whose
+ // marker precedes any reply boundary.
+ if (isForwardedMessage(content)) return content;
+
+ if (contentType === "html") {
+ // Gmail wraps quoted replies in <div class="gmail_quote">
+ // Remove it and everything after it
+ const gmailQuoteIdx = content.search(
+ /<div[^>]*class\s*=\s*["'][^"']*gmail_quote[^"']*["'][^>]*>/i
+ );
+ if (gmailQuoteIdx !== -1) {
+ return content.substring(0, gmailQuoteIdx).trim();
+ }
+
+ // Some clients use <blockquote> with gmail_quote class
+ const blockquoteIdx = content.search(
+ /<blockquote[^>]*class\s*=\s*["'][^"']*gmail_quote[^"']*["'][^>]*>/i
+ );
+ if (blockquoteIdx !== -1) {
+ return content.substring(0, blockquoteIdx).trim();
+ }
+
+ // Microsoft Outlook-style: <div id="appendonsend"></div> followed by quoted content,
+ // or a <hr> divider followed by "From:" header pattern
+ const outlookDivIdx = content.search(
+ /<div[^>]*id\s*=\s*["'](?:appendonsend|divRplyFwdMsg)["'][^>]*>/i
+ );
+ if (outlookDivIdx !== -1) {
+ return content.substring(0, outlookDivIdx).trim();
+ }
+
+ // Outlook (desktop, OWA, and corporate Exchange clients) wraps replies
+ // with a "From: / Sent: / To: / Subject:" header block. The markup
+ // varies — sometimes `<b>` or `<strong>`, sometimes `<span
+ // style="font-weight:bold">`, sometimes a `MsoNormal` paragraph with
+ // no inline bold at all (Gowling-style corporate Exchange). Try the
+ // tight bold-wrapped pattern first, then fall back to a tag-agnostic
+ // boundary match.
+ const outlookHeaderRe =
+ /<(b|strong)[^>]*>\s*From:?\s*<\/\1>[\s\S]{0,1000}<(b|strong)[^>]*>\s*Sent:?\s*<\/\2>[\s\S]{0,1000}<(b|strong)[^>]*>\s*To:?\s*<\/\3>[\s\S]{0,1000}<(b|strong)[^>]*>\s*Subject:?\s*<\/\4>/i;
+ const outlookHeaderMatch = content.match(outlookHeaderRe);
+ const fromIdx =
+ outlookHeaderMatch?.index ?? findOutlookHeaderTagAgnostic(content);
+ if (fromIdx !== -1) {
+ const lookbackStart = Math.max(0, fromIdx - 1000);
+ const lookback = content.substring(lookbackStart, fromIdx);
+ // Prefer the latest structural divider (border-top div or <hr>)
+ // before the From: tag — that's the user/quoted boundary in
+ // Outlook's standard reply format.
+ const dividerRe =
+ /<hr\b[^>]*>|<div[^>]*style\s*=\s*["'][^"']*border-top\s*:[^"']*["'][^>]*>/gi;
+ let lastDivider = -1;
+ let match: RegExpExecArray | null;
+ while ((match = dividerRe.exec(lookback)) !== null) {
+ lastDivider = match.index;
+ }
+ let cut = fromIdx;
+ if (lastDivider !== -1) {
+ cut = lookbackStart + lastDivider;
+ } else {
+ // No divider — cut at the start of the wrapping <p> or <div>.
+ const lastP = lookback.lastIndexOf("<p");
+ const lastDiv = lookback.lastIndexOf("<div");
+ const wrapper = Math.max(lastP, lastDiv);
+ if (wrapper !== -1) {
+ cut = lookbackStart + wrapper;
+ }
+ }
+ return content.substring(0, cut).trim();
+ }
+
+ return content;
+ }
+
+ // Plain text: look for "On ... wrote:" followed by quoted lines
+ const lines = content.split("\n");
+ for (let i = 0; i < lines.length; i++) {
+ const line = lines[i].trim();
+
+ // "On [date], [name] wrote:" or "On [date], [name] <email> wrote:"
+ if (/^On .+ wrote:\s*$/.test(line)) {
+ // Verify next non-empty line starts with ">" (actual quoted content)
+ const nextContentLine = lines.slice(i + 1).find((l) => l.trim() !== "");
+ if (nextContentLine && nextContentLine.trim().startsWith(">")) {
+ return lines
+ .slice(0, i)
+ .join("\n")
+ .trim();
+ }
+ }
+ }
+
+ return content;
+}
+
+/**
+ * Detects a forwarded message so {@link stripQuotedReply} can preserve it.
+ * Matches Gmail's dashed "---------- Forwarded message ---------" marker and
+ * Apple Mail's "Begin forwarded message:". Returns false when a reply boundary
+ * ("On … wrote:") precedes the forward marker — that's a reply quoting a
+ * forward, which the reply-stripper should still trim.
+ */
+function isForwardedMessage(content: string): boolean {
+ const fwdIdx = content.search(
+ /(-{2,}\s*Forwarded message\s*-{2,}|Begin forwarded message:)/i
+ );
+ if (fwdIdx === -1) return false;
+ const replyIdx = content.search(/On\s[\s\S]{0,200}?\swrote:/i);
+ if (replyIdx !== -1 && replyIdx < fwdIdx) return false;
+ return true;
+}

connectors/outlook-mail/LICENSE

@@ -0,0 +1,21 @@
+MIT License
+
+Copyright (c) 2026 Plot Technologies Inc.
+
+Permission is hereby granted, free of charge, to any person obtaining a copy
+of this software and associated documentation files (the "Software"), to deal
+in the Software without restriction, including without limitation the rights
+to use, copy, modify, merge, publish, distribute, sublicense, and/or sell
+copies of the Software, and to permit persons to whom the Software is
+furnished to do so, subject to the following conditions:
+
+The above copyright notice and this permission notice shall be included in all
+copies or substantial portions of the Software.
+
+THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF ANY KIND, EXPRESS OR
+IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF MERCHANTABILITY,
+FITNESS FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT SHALL THE
+AUTHORS OR COPYRIGHT HOLDERS BE LIABLE FOR ANY CLAIM, DAMAGES OR OTHER
+LIABILITY, WHETHER IN AN ACTION OF CONTRACT, TORT OR OTHERWISE, ARISING FROM,
+OUT OF OR IN CONNECTION WITH THE SOFTWARE OR THE USE OR OTHER DEALINGS IN THE
+SOFTWARE.

connectors/outlook-mail/README.md

@@ -0,0 +1,98 @@
+# Outlook Mail Connector
+
+Syncs Microsoft Outlook mail (personal outlook.com and work/school Microsoft 365
+accounts) into Plot via Microsoft Graph. Each Outlook conversation becomes a
+Plot thread; each message becomes a note on that thread.
+
+## What it syncs
+
+- **Channels** are mail folders (`/me/mailFolders`). Inbox and Sent Items are
+ enabled by default; Junk, Deleted Items, Drafts, Outbox, and Conversation
+ History are never offered. Enabling a folder backfills its history;
+ incremental changes are mailbox-wide (one Graph change-notification
+ subscription on `/me/messages`) and routed to whichever enabled folder the
+ conversation lives in.
+- **Notes** are keyed on `internetMessageId`, so folder moves and the echo of
+ mail sent from Plot dedupe cleanly. Drafts are skipped (Outlook autosave
+ would churn notes).
+- **Attachments** sync as file references and download on demand. Inline
+ images are skipped.
+- **Facets** for Plot's classifier come from RFC 5322 headers (List-Id,
+ Precedence, Auto-Submitted, …) plus Outlook's Focused Inbox
+ (`inferenceClassification`).
+
+## Two-way sync
+
+| Plot action | Outlook effect |
+|---|---|
+| Mark thread read / unread | `isRead` PATCHed on the conversation's messages (unread marks the latest message, read clears all) |
+| Add / remove To Do | `flag.flagStatus` set to `flagged` on the latest message / cleared on all flagged messages |
+| Reply on a thread | Graph `createReply` draft, recipients constrained by the note's access contacts, then sent |
+| New email thread | Graph draft + send, To/CC/BCC from the compose roster |
+
+Outlook-side changes flow back the other way: reading, flagging, replying, and
+new mail all arrive via change notifications (with a 60-minute delta-query
+self-heal catching anything push delivery misses).
+
+## OAuth scopes
+
+| Scope | Why |
+|---|---|
+| `Mail.ReadWrite` | Read folders/messages, update read + flag state, create drafts |
+| `Mail.Send` | Send replies and new mail composed in Plot |
+| `People.Read` | Resolve display names for frequent correspondents who aren't saved contacts |
+| `Contacts.Read` | Resolve display names from saved contacts |
+
+## Known limitations
+
+- **Avatars are not enriched.** Microsoft Graph photo endpoints return
+ auth-gated binary data with no public URL, so there is nothing to store in
+ `contact.avatar`. Contact *names* are enriched from People/Contacts; avatars
+ fall back to Gravatar on the client.
+- **Personal accounts degrade gracefully.** The People API returns limited
+ data for consumer accounts and may 403; enrichment is best-effort per
+ address. Focused Inbox signals are used only when present.
+- Reply bodies are sent as plain text without the quoted-history block (Plot
+ threads already carry the history as notes) — same behavior as the Gmail
+ connector.
+
+## Manual E2E test plan
+
+Prerequisites: the Azure app registration (see `docs/outlook.md` in the core
+repo) must include the delegated scopes `Mail.ReadWrite`, `Mail.Send`,
+`People.Read`, `Contacts.Read`; `AUTH_MICROSOFT_ID`/`AUTH_MICROSOFT_SECRET`
+set in `workers/api/.dev.vars`; tunnel running (`pnpm tunnel:start`) so Graph
+can reach the webhook endpoint (subscriptions are skipped on localhost).
+
+Run the pass twice: once with a **personal** (outlook.com) account and once
+with a **work/school** (Microsoft 365) account.
+
+1. **Connect + channels** — add an Outlook Mail connection; verify the folder
+ list excludes Junk/Deleted/Drafts and defaults Inbox + Sent Items on.
+2. **Backfill** — enable Inbox; verify threads appear with correct titles,
+ per-message notes, participants, timestamps, and that the "Syncing…" badge
+ clears. No unread badges from backfilled mail.
+3. **Inbound incremental** — send mail to the account from outside; verify the
+ thread appears (or extends) within seconds via the subscription.
+4. **Unread round-trip** — read a thread in Plot → message marked read in
+ Outlook; mark a thread unread in Outlook → unread in Plot. Verify no
+ echo loop (state settles after one hop each way).
+5. **Flag ↔ To Do round-trip** — flag in Outlook → thread becomes a Plot
+ To Do; toggle To Do off in Plot → flag cleared in Outlook.
+6. **Reply from Plot** — reply on a synced thread; verify recipients (To/Cc),
+ threading in Outlook, and that the sent message does NOT duplicate as a
+ new note when it syncs back.
+7. **Reply with attachment** — attach a small (<3 MB) and a large (>3 MB)
+ file; verify both arrive in Outlook.
+8. **Compose from Plot** — new email thread to a typed address + a contact
+ with CC; verify delivery, BCC kept out of visible headers, and the
+ originating note binds to the sent message.
+9. **Attachment download** — open a synced message's attachment in Plot.
+10. **Contact names** — verify senders not in the address book still resolve
+ display names where People data exists (work tenant), and degrade to
+ email-only on personal accounts.
+11. **Self-heal** — stop the tunnel for >1 hour, send external mail, restart;
+ verify the hourly delta sweep ingests the missed mail and the
+ subscription is renewed (check `selfHealCheck` log lines).
+12. **Teardown** — disable all folders; verify the Graph subscription is
+ deleted (no further webhook traffic) and re-enabling rebuilds it.

connectors/outlook-mail/package.json

@@ -0,0 +1,48 @@
+{
+ "name": "@plotday/connector-outlook-mail",
+ "plotTwistId": "6c3773dd-e820-4043-a5bc-f4e299ca1a19",
+ "displayName": "Outlook Mail",
+ "description": "Send and reply to Outlook email, tracking threads for follow-up and snoozing the rest.",
+ "category": "messaging",
+ "logoUrl": "https://api.iconify.design/simple-icons/microsoftoutlook.svg",
+ "publisher": "Plot",
+ "publisherUrl": "https://plot.day",
+ "author": "Plot <team@plot.day> (https://plot.day)",
+ "license": "MIT",
+ "version": "0.1.0",
+ "type": "module",
+ "main": "./dist/index.js",
+ "types": "./dist/index.d.ts",
+ "exports": {
+ ".": {
+ "@plotday/connector": "./src/index.ts",
+ "types": "./dist/index.d.ts",
+ "default": "./dist/index.js"
+ }
+ },
+ "private": true,
+ "scripts": {
+ "build": "tsc",
+ "clean": "rm -rf dist",
+ "deploy": "plot deploy",
+ "lint": "plot lint",
+ "test": "vitest run",
+ "test:watch": "vitest"
+ },
+ "dependencies": {
+ "@plotday/email-classifier": "workspace:^",
+ "@plotday/twister": "workspace:^"
+ },
+ "devDependencies": {
+ "typescript": "^5.9.3",
+ "vitest": "^2.1.8"
+ },
+ "repository": {
+ "type": "git",
+ "url": "https://github.com/plotday/plot.git",
+ "directory": "connectors/outlook-mail"
+ },
+ "homepage": "https://plot.day",
+ "bugs": { "url": "https://github.com/plotday/plot/issues" },
+ "keywords": ["plot", "connector", "outlook", "microsoft", "email", "messaging"]
+}

connectors/outlook-mail/src/email-parsing.test.ts

@@ -0,0 +1,24 @@
+import { describe, expect, it } from "vitest";
+import { stripQuotedReply } from "./email-parsing";
+
+describe("stripQuotedReply", () => {
+ it("cuts Outlook appendonsend reply chains", () => {
+ const html = `<div>New content</div><div id="appendonsend"></div><div>From: A<br>Sent: B<br>To: C<br>Subject: D</div>`;
+ expect(stripQuotedReply(html, "html")).toBe("<div>New content</div>");
+ });
+
+ it("cuts gmail_quote blocks from cross-client replies", () => {
+ const html = `<p>Reply</p><div class="gmail_quote">old</div>`;
+ expect(stripQuotedReply(html, "html")).toBe("<p>Reply</p>");
+ });
+
+ it("preserves forwarded messages", () => {
+ const text = "FYI\n---------- Forwarded message ---------\nFrom: x";
+ expect(stripQuotedReply(text, "text")).toBe(text);
+ });
+
+ it("cuts plain-text 'On ... wrote:' quotes", () => {
+ const text = "Thanks!\nOn Tue, Jun 10, 2026, Kris wrote:\n> earlier";
+ expect(stripQuotedReply(text, "text")).toBe("Thanks!");
+ });
+});

connectors/outlook-mail/src/email-parsing.ts

@@ -0,0 +1,153 @@
+// Quote-stripping helpers shared with the Gmail connector (copied from
+// gmail/src/gmail-api.ts — keep in sync).
+
+/**
+ * Locates the start of an Outlook-style "From: / Sent: / To: / Subject:"
+ * reply header even when the field labels are not wrapped in `<b>` or
+ * `<strong>` — e.g. corporate Exchange / Outlook variants that put the
+ * label in a `<span style="font-weight:bold">`, a `<font>` tag, or a
+ * plain `MsoNormal` paragraph with no inline bold at all.
+ *
+ * Strategy: replace every HTML tag with a same-length run of spaces so
+ * character offsets in the stripped text still map 1:1 back to the
+ * original. Then require each label to start at a structural boundary
+ * (start of string, a real newline, or 3+ whitespace chars — the smallest
+ * gap any HTML block tag produces when replaced). That anchor is what
+ * keeps user-written prose from false-matching.
+ *
+ * Returns the index of "From:" in the original content, or -1 if no
+ * Outlook reply header is found.
+ */
+export function findOutlookHeaderTagAgnostic(content: string): number {
+ const flat = content.replace(/<[^>]*>/g, (m) => " ".repeat(m.length));
+ const re =
+ /(?<=^|\n|[ \t]{3,})From:[\s\S]{0,1500}?(?<=\n|[ \t]{3,})Sent:[\s\S]{0,800}?(?<=\n|[ \t]{3,})To:[\s\S]{0,1500}?(?<=\n|[ \t]{3,})Subject:/i;
+ const m = flat.match(re);
+ return m?.index ?? -1;
+}
+
+/**
+ * Strips quoted reply content from an email body.
+ * Since Plot shows each message as a separate note in a thread,
+ * the quoted previous messages are redundant noise.
+ */
+export function stripQuotedReply(
+ content: string,
+ contentType: "text" | "html"
+): string {
+ if (!content) return content;
+
+ // Forwarded messages: the forwarded email IS the content the user wants to
+ // read. Gmail/Apple Mail wrap a forward in the same quote container Gmail uses
+ // for reply quotes, so the reply-stripping below would delete the whole body
+ // and leave an empty note. Keep the content as-is when it's a forward whose
+ // marker precedes any reply boundary.
+ if (isForwardedMessage(content)) return content;
+
+ if (contentType === "html") {
+ // Gmail wraps quoted replies in <div class="gmail_quote">
+ // Remove it and everything after it
+ const gmailQuoteIdx = content.search(
+ /<div[^>]*class\s*=\s*["'][^"']*gmail_quote[^"']*["'][^>]*>/i
+ );
+ if (gmailQuoteIdx !== -1) {
+ return content.substring(0, gmailQuoteIdx).trim();
+ }
+
+ // Some clients use <blockquote> with gmail_quote class
+ const blockquoteIdx = content.search(
+ /<blockquote[^>]*class\s*=\s*["'][^"']*gmail_quote[^"']*["'][^>]*>/i
+ );
+ if (blockquoteIdx !== -1) {
+ return content.substring(0, blockquoteIdx).trim();
+ }
+
+ // Microsoft Outlook-style: <div id="appendonsend"></div> followed by quoted content,
+ // or a <hr> divider followed by "From:" header pattern
+ const outlookDivIdx = content.search(
+ /<div[^>]*id\s*=\s*["'](?:appendonsend|divRplyFwdMsg)["'][^>]*>/i
+ );
+ if (outlookDivIdx !== -1) {
+ return content.substring(0, outlookDivIdx).trim();
+ }
+
+ // Outlook (desktop, OWA, and corporate Exchange clients) wraps replies
+ // with a "From: / Sent: / To: / Subject:" header block. The markup
+ // varies — sometimes `<b>` or `<strong>`, sometimes `<span
+ // style="font-weight:bold">`, sometimes a `MsoNormal` paragraph with
+ // no inline bold at all (Gowling-style corporate Exchange). Try the
+ // tight bold-wrapped pattern first, then fall back to a tag-agnostic
+ // boundary match.
+ const outlookHeaderRe =
+ /<(b|strong)[^>]*>\s*From:?\s*<\/\1>[\s\S]{0,1000}<(b|strong)[^>]*>\s*Sent:?\s*<\/\2>[\s\S]{0,1000}<(b|strong)[^>]*>\s*To:?\s*<\/\3>[\s\S]{0,1000}<(b|strong)[^>]*>\s*Subject:?\s*<\/\4>/i;
+ const outlookHeaderMatch = content.match(outlookHeaderRe);
+ const fromIdx =
+ outlookHeaderMatch?.index ?? findOutlookHeaderTagAgnostic(content);
+ if (fromIdx !== -1) {
+ const lookbackStart = Math.max(0, fromIdx - 1000);
+ const lookback = content.substring(lookbackStart, fromIdx);
+ // Prefer the latest structural divider (border-top div or <hr>)
+ // before the From: tag — that's the user/quoted boundary in
+ // Outlook's standard reply format.
+ const dividerRe =
+ /<hr\b[^>]*>|<div[^>]*style\s*=\s*["'][^"']*border-top\s*:[^"']*["'][^>]*>/gi;
+ let lastDivider = -1;
+ let match: RegExpExecArray | null;
+ while ((match = dividerRe.exec(lookback)) !== null) {
+ lastDivider = match.index;
+ }
+ let cut = fromIdx;
+ if (lastDivider !== -1) {
+ cut = lookbackStart + lastDivider;
+ } else {
+ // No divider — cut at the start of the wrapping <p> or <div>.
+ const lastP = lookback.lastIndexOf("<p");
+ const lastDiv = lookback.lastIndexOf("<div");
+ const wrapper = Math.max(lastP, lastDiv);
+ if (wrapper !== -1) {
+ cut = lookbackStart + wrapper;
+ }
+ }
+ return content.substring(0, cut).trim();
+ }
+
+ return content;
+ }
+
+ // Plain text: look for "On ... wrote:" followed by quoted lines
+ const lines = content.split("\n");
+ for (let i = 0; i < lines.length; i++) {
+ const line = lines[i].trim();
+
+ // "On [date], [name] wrote:" or "On [date], [name] <email> wrote:"
+ if (/^On .+ wrote:\s*$/.test(line)) {
+ // Verify next non-empty line starts with ">" (actual quoted content)
+ const nextContentLine = lines.slice(i + 1).find((l) => l.trim() !== "");
+ if (nextContentLine && nextContentLine.trim().startsWith(">")) {
+ return lines
+ .slice(0, i)
+ .join("\n")
+ .trim();
+ }
+ }
+ }
+
+ return content;
+}
+
+/**
+ * Detects a forwarded message so {@link stripQuotedReply} can preserve it.
+ * Matches Gmail's dashed "---------- Forwarded message ---------" marker and
+ * Apple Mail's "Begin forwarded message:". Returns false when a reply boundary
+ * ("On … wrote:") precedes the forward marker — that's a reply quoting a
+ * forward, which the reply-stripper should still trim.
+ */
+function isForwardedMessage(content: string): boolean {
+ const fwdIdx = content.search(
+ /(-{2,}\s*Forwarded message\s*-{2,}|Begin forwarded message:)/i
+ );
+ if (fwdIdx === -1) return false;
+ const replyIdx = content.search(/On\s[\s\S]{0,200}?\swrote:/i);
+ if (replyIdx !== -1 && replyIdx < fwdIdx) return false;
+ return true;
+}

connectors/outlook-mail/LICENSE

@@ -0,0 +1,21 @@
+MIT License
+
+Copyright (c) 2026 Plot Technologies Inc.
+
+Permission is hereby granted, free of charge, to any person obtaining a copy
+of this software and associated documentation files (the "Software"), to deal
+in the Software without restriction, including without limitation the rights
+to use, copy, modify, merge, publish, distribute, sublicense, and/or sell
+copies of the Software, and to permit persons to whom the Software is
+furnished to do so, subject to the following conditions:
+
+The above copyright notice and this permission notice shall be included in all
+copies or substantial portions of the Software.
+
+THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF ANY KIND, EXPRESS OR
+IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF MERCHANTABILITY,
+FITNESS FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT SHALL THE
+AUTHORS OR COPYRIGHT HOLDERS BE LIABLE FOR ANY CLAIM, DAMAGES OR OTHER
+LIABILITY, WHETHER IN AN ACTION OF CONTRACT, TORT OR OTHERWISE, ARISING FROM,
+OUT OF OR IN CONNECTION WITH THE SOFTWARE OR THE USE OR OTHER DEALINGS IN THE
+SOFTWARE.

connectors/outlook-mail/README.md

@@ -0,0 +1,98 @@
+# Outlook Mail Connector
+
+Syncs Microsoft Outlook mail (personal outlook.com and work/school Microsoft 365
+accounts) into Plot via Microsoft Graph. Each Outlook conversation becomes a
+Plot thread; each message becomes a note on that thread.
+
+## What it syncs
+
+- **Channels** are mail folders (`/me/mailFolders`). Inbox and Sent Items are
+ enabled by default; Junk, Deleted Items, Drafts, Outbox, and Conversation
+ History are never offered. Enabling a folder backfills its history;
+ incremental changes are mailbox-wide (one Graph change-notification
+ subscription on `/me/messages`) and routed to whichever enabled folder the
+ conversation lives in.
+- **Notes** are keyed on `internetMessageId`, so folder moves and the echo of
+ mail sent from Plot dedupe cleanly. Drafts are skipped (Outlook autosave
+ would churn notes).
+- **Attachments** sync as file references and download on demand. Inline
+ images are skipped.
+- **Facets** for Plot's classifier come from RFC 5322 headers (List-Id,
+ Precedence, Auto-Submitted, …) plus Outlook's Focused Inbox
+ (`inferenceClassification`).
+
+## Two-way sync
+
+| Plot action | Outlook effect |
+|---|---|
+| Mark thread read / unread | `isRead` PATCHed on the conversation's messages (unread marks the latest message, read clears all) |
+| Add / remove To Do | `flag.flagStatus` set to `flagged` on the latest message / cleared on all flagged messages |
+| Reply on a thread | Graph `createReply` draft, recipients constrained by the note's access contacts, then sent |
+| New email thread | Graph draft + send, To/CC/BCC from the compose roster |
+
+Outlook-side changes flow back the other way: reading, flagging, replying, and
+new mail all arrive via change notifications (with a 60-minute delta-query
+self-heal catching anything push delivery misses).
+
+## OAuth scopes
+
+| Scope | Why |
+|---|---|
+| `Mail.ReadWrite` | Read folders/messages, update read + flag state, create drafts |
+| `Mail.Send` | Send replies and new mail composed in Plot |
+| `People.Read` | Resolve display names for frequent correspondents who aren't saved contacts |
+| `Contacts.Read` | Resolve display names from saved contacts |
+
+## Known limitations
+
+- **Avatars are not enriched.** Microsoft Graph photo endpoints return
+ auth-gated binary data with no public URL, so there is nothing to store in
+ `contact.avatar`. Contact *names* are enriched from People/Contacts; avatars
+ fall back to Gravatar on the client.
+- **Personal accounts degrade gracefully.** The People API returns limited
+ data for consumer accounts and may 403; enrichment is best-effort per
+ address. Focused Inbox signals are used only when present.
+- Reply bodies are sent as plain text without the quoted-history block (Plot
+ threads already carry the history as notes) — same behavior as the Gmail
+ connector.
+
+## Manual E2E test plan
+
+Prerequisites: the Azure app registration (see `docs/outlook.md` in the core
+repo) must include the delegated scopes `Mail.ReadWrite`, `Mail.Send`,
+`People.Read`, `Contacts.Read`; `AUTH_MICROSOFT_ID`/`AUTH_MICROSOFT_SECRET`
+set in `workers/api/.dev.vars`; tunnel running (`pnpm tunnel:start`) so Graph
+can reach the webhook endpoint (subscriptions are skipped on localhost).
+
+Run the pass twice: once with a **personal** (outlook.com) account and once
+with a **work/school** (Microsoft 365) account.
+
+1. **Connect + channels** — add an Outlook Mail connection; verify the folder
+ list excludes Junk/Deleted/Drafts and defaults Inbox + Sent Items on.
+2. **Backfill** — enable Inbox; verify threads appear with correct titles,
+ per-message notes, participants, timestamps, and that the "Syncing…" badge
+ clears. No unread badges from backfilled mail.
+3. **Inbound incremental** — send mail to the account from outside; verify the
+ thread appears (or extends) within seconds via the subscription.
+4. **Unread round-trip** — read a thread in Plot → message marked read in
+ Outlook; mark a thread unread in Outlook → unread in Plot. Verify no
+ echo loop (state settles after one hop each way).
+5. **Flag ↔ To Do round-trip** — flag in Outlook → thread becomes a Plot
+ To Do; toggle To Do off in Plot → flag cleared in Outlook.
+6. **Reply from Plot** — reply on a synced thread; verify recipients (To/Cc),
+ threading in Outlook, and that the sent message does NOT duplicate as a
+ new note when it syncs back.
+7. **Reply with attachment** — attach a small (<3 MB) and a large (>3 MB)
+ file; verify both arrive in Outlook.
+8. **Compose from Plot** — new email thread to a typed address + a contact
+ with CC; verify delivery, BCC kept out of visible headers, and the
+ originating note binds to the sent message.
+9. **Attachment download** — open a synced message's attachment in Plot.
+10. **Contact names** — verify senders not in the address book still resolve
+ display names where People data exists (work tenant), and degrade to
+ email-only on personal accounts.
+11. **Self-heal** — stop the tunnel for >1 hour, send external mail, restart;
+ verify the hourly delta sweep ingests the missed mail and the
+ subscription is renewed (check `selfHealCheck` log lines).
+12. **Teardown** — disable all folders; verify the Graph subscription is
+ deleted (no further webhook traffic) and re-enabling rebuilds it.

connectors/outlook-mail/package.json

@@ -0,0 +1,48 @@
+{
+ "name": "@plotday/connector-outlook-mail",
+ "plotTwistId": "6c3773dd-e820-4043-a5bc-f4e299ca1a19",
+ "displayName": "Outlook Mail",
+ "description": "Send and reply to Outlook email, tracking threads for follow-up and snoozing the rest.",
+ "category": "messaging",
+ "logoUrl": "https://api.iconify.design/simple-icons/microsoftoutlook.svg",
+ "publisher": "Plot",
+ "publisherUrl": "https://plot.day",
+ "author": "Plot <team@plot.day> (https://plot.day)",
+ "license": "MIT",
+ "version": "0.1.0",
+ "type": "module",
+ "main": "./dist/index.js",
+ "types": "./dist/index.d.ts",
+ "exports": {
+ ".": {
+ "@plotday/connector": "./src/index.ts",
+ "types": "./dist/index.d.ts",
+ "default": "./dist/index.js"
+ }
+ },
+ "private": true,
+ "scripts": {
+ "build": "tsc",
+ "clean": "rm -rf dist",
+ "deploy": "plot deploy",
+ "lint": "plot lint",
+ "test": "vitest run",
+ "test:watch": "vitest"
+ },
+ "dependencies": {
+ "@plotday/email-classifier": "workspace:^",
+ "@plotday/twister": "workspace:^"
+ },
+ "devDependencies": {
+ "typescript": "^5.9.3",
+ "vitest": "^2.1.8"
+ },
+ "repository": {
+ "type": "git",
+ "url": "https://github.com/plotday/plot.git",
+ "directory": "connectors/outlook-mail"
+ },
+ "homepage": "https://plot.day",
+ "bugs": { "url": "https://github.com/plotday/plot/issues" },
+ "keywords": ["plot", "connector", "outlook", "microsoft", "email", "messaging"]
+}

connectors/outlook-mail/src/email-parsing.test.ts

@@ -0,0 +1,24 @@
+import { describe, expect, it } from "vitest";
+import { stripQuotedReply } from "./email-parsing";
+
+describe("stripQuotedReply", () => {
+ it("cuts Outlook appendonsend reply chains", () => {
+ const html = `<div>New content</div><div id="appendonsend"></div><div>From: A<br>Sent: B<br>To: C<br>Subject: D</div>`;
+ expect(stripQuotedReply(html, "html")).toBe("<div>New content</div>");
+ });
+
+ it("cuts gmail_quote blocks from cross-client replies", () => {
+ const html = `<p>Reply</p><div class="gmail_quote">old</div>`;
+ expect(stripQuotedReply(html, "html")).toBe("<p>Reply</p>");
+ });
+
+ it("preserves forwarded messages", () => {
+ const text = "FYI\n---------- Forwarded message ---------\nFrom: x";
+ expect(stripQuotedReply(text, "text")).toBe(text);
+ });
+
+ it("cuts plain-text 'On ... wrote:' quotes", () => {
+ const text = "Thanks!\nOn Tue, Jun 10, 2026, Kris wrote:\n> earlier";
+ expect(stripQuotedReply(text, "text")).toBe("Thanks!");
+ });
+});

connectors/outlook-mail/src/email-parsing.ts

@@ -0,0 +1,153 @@
+// Quote-stripping helpers shared with the Gmail connector (copied from
+// gmail/src/gmail-api.ts — keep in sync).
+
+/**
+ * Locates the start of an Outlook-style "From: / Sent: / To: / Subject:"
+ * reply header even when the field labels are not wrapped in `<b>` or
+ * `<strong>` — e.g. corporate Exchange / Outlook variants that put the
+ * label in a `<span style="font-weight:bold">`, a `<font>` tag, or a
+ * plain `MsoNormal` paragraph with no inline bold at all.
+ *
+ * Strategy: replace every HTML tag with a same-length run of spaces so
+ * character offsets in the stripped text still map 1:1 back to the
+ * original. Then require each label to start at a structural boundary
+ * (start of string, a real newline, or 3+ whitespace chars — the smallest
+ * gap any HTML block tag produces when replaced). That anchor is what
+ * keeps user-written prose from false-matching.
+ *
+ * Returns the index of "From:" in the original content, or -1 if no
+ * Outlook reply header is found.
+ */
+export function findOutlookHeaderTagAgnostic(content: string): number {
+ const flat = content.replace(/<[^>]*>/g, (m) => " ".repeat(m.length));
+ const re =
+ /(?<=^|\n|[ \t]{3,})From:[\s\S]{0,1500}?(?<=\n|[ \t]{3,})Sent:[\s\S]{0,800}?(?<=\n|[ \t]{3,})To:[\s\S]{0,1500}?(?<=\n|[ \t]{3,})Subject:/i;
+ const m = flat.match(re);
+ return m?.index ?? -1;
+}
+
+/**
+ * Strips quoted reply content from an email body.
+ * Since Plot shows each message as a separate note in a thread,
+ * the quoted previous messages are redundant noise.
+ */
+export function stripQuotedReply(
+ content: string,
+ contentType: "text" | "html"
+): string {
+ if (!content) return content;
+
+ // Forwarded messages: the forwarded email IS the content the user wants to
+ // read. Gmail/Apple Mail wrap a forward in the same quote container Gmail uses
+ // for reply quotes, so the reply-stripping below would delete the whole body
+ // and leave an empty note. Keep the content as-is when it's a forward whose
+ // marker precedes any reply boundary.
+ if (isForwardedMessage(content)) return content;
+
+ if (contentType === "html") {
+ // Gmail wraps quoted replies in <div class="gmail_quote">
+ // Remove it and everything after it
+ const gmailQuoteIdx = content.search(
+ /<div[^>]*class\s*=\s*["'][^"']*gmail_quote[^"']*["'][^>]*>/i
+ );
+ if (gmailQuoteIdx !== -1) {
+ return content.substring(0, gmailQuoteIdx).trim();
+ }
+
+ // Some clients use <blockquote> with gmail_quote class
+ const blockquoteIdx = content.search(
+ /<blockquote[^>]*class\s*=\s*["'][^"']*gmail_quote[^"']*["'][^>]*>/i
+ );
+ if (blockquoteIdx !== -1) {
+ return content.substring(0, blockquoteIdx).trim();
+ }
+
+ // Microsoft Outlook-style: <div id="appendonsend"></div> followed by quoted content,
+ // or a <hr> divider followed by "From:" header pattern
+ const outlookDivIdx = content.search(
+ /<div[^>]*id\s*=\s*["'](?:appendonsend|divRplyFwdMsg)["'][^>]*>/i
+ );
+ if (outlookDivIdx !== -1) {
+ return content.substring(0, outlookDivIdx).trim();
+ }
+
+ // Outlook (desktop, OWA, and corporate Exchange clients) wraps replies
+ // with a "From: / Sent: / To: / Subject:" header block. The markup
+ // varies — sometimes `<b>` or `<strong>`, sometimes `<span
+ // style="font-weight:bold">`, sometimes a `MsoNormal` paragraph with
+ // no inline bold at all (Gowling-style corporate Exchange). Try the
+ // tight bold-wrapped pattern first, then fall back to a tag-agnostic
+ // boundary match.
+ const outlookHeaderRe =
+ /<(b|strong)[^>]*>\s*From:?\s*<\/\1>[\s\S]{0,1000}<(b|strong)[^>]*>\s*Sent:?\s*<\/\2>[\s\S]{0,1000}<(b|strong)[^>]*>\s*To:?\s*<\/\3>[\s\S]{0,1000}<(b|strong)[^>]*>\s*Subject:?\s*<\/\4>/i;
+ const outlookHeaderMatch = content.match(outlookHeaderRe);
+ const fromIdx =
+ outlookHeaderMatch?.index ?? findOutlookHeaderTagAgnostic(content);
+ if (fromIdx !== -1) {
+ const lookbackStart = Math.max(0, fromIdx - 1000);
+ const lookback = content.substring(lookbackStart, fromIdx);
+ // Prefer the latest structural divider (border-top div or <hr>)
+ // before the From: tag — that's the user/quoted boundary in
+ // Outlook's standard reply format.
+ const dividerRe =
+ /<hr\b[^>]*>|<div[^>]*style\s*=\s*["'][^"']*border-top\s*:[^"']*["'][^>]*>/gi;
+ let lastDivider = -1;
+ let match: RegExpExecArray | null;
+ while ((match = dividerRe.exec(lookback)) !== null) {
+ lastDivider = match.index;
+ }
+ let cut = fromIdx;
+ if (lastDivider !== -1) {
+ cut = lookbackStart + lastDivider;
+ } else {
+ // No divider — cut at the start of the wrapping <p> or <div>.
+ const lastP = lookback.lastIndexOf("<p");
+ const lastDiv = lookback.lastIndexOf("<div");
+ const wrapper = Math.max(lastP, lastDiv);
+ if (wrapper !== -1) {
+ cut = lookbackStart + wrapper;
+ }
+ }
+ return content.substring(0, cut).trim();
+ }
+
+ return content;
+ }
+
+ // Plain text: look for "On ... wrote:" followed by quoted lines
+ const lines = content.split("\n");
+ for (let i = 0; i < lines.length; i++) {
+ const line = lines[i].trim();
+
+ // "On [date], [name] wrote:" or "On [date], [name] <email> wrote:"
+ if (/^On .+ wrote:\s*$/.test(line)) {
+ // Verify next non-empty line starts with ">" (actual quoted content)
+ const nextContentLine = lines.slice(i + 1).find((l) => l.trim() !== "");
+ if (nextContentLine && nextContentLine.trim().startsWith(">")) {
+ return lines
+ .slice(0, i)
+ .join("\n")
+ .trim();
+ }
+ }
+ }
+
+ return content;
+}
+
+/**
+ * Detects a forwarded message so {@link stripQuotedReply} can preserve it.
+ * Matches Gmail's dashed "---------- Forwarded message ---------" marker and
+ * Apple Mail's "Begin forwarded message:". Returns false when a reply boundary
+ * ("On … wrote:") precedes the forward marker — that's a reply quoting a
+ * forward, which the reply-stripper should still trim.
+ */
+function isForwardedMessage(content: string): boolean {
+ const fwdIdx = content.search(
+ /(-{2,}\s*Forwarded message\s*-{2,}|Begin forwarded message:)/i
+ );
+ if (fwdIdx === -1) return false;
+ const replyIdx = content.search(/On\s[\s\S]{0,200}?\swrote:/i);
+ if (replyIdx !== -1 && replyIdx < fwdIdx) return false;
+ return true;
+}

connectors/outlook-mail/LICENSE

@@ -0,0 +1,21 @@
+MIT License
+
+Copyright (c) 2026 Plot Technologies Inc.
+
+Permission is hereby granted, free of charge, to any person obtaining a copy
+of this software and associated documentation files (the "Software"), to deal
+in the Software without restriction, including without limitation the rights
+to use, copy, modify, merge, publish, distribute, sublicense, and/or sell
+copies of the Software, and to permit persons to whom the Software is
+furnished to do so, subject to the following conditions:
+
+The above copyright notice and this permission notice shall be included in all
+copies or substantial portions of the Software.
+
+THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF ANY KIND, EXPRESS OR
+IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF MERCHANTABILITY,
+FITNESS FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT SHALL THE
+AUTHORS OR COPYRIGHT HOLDERS BE LIABLE FOR ANY CLAIM, DAMAGES OR OTHER
+LIABILITY, WHETHER IN AN ACTION OF CONTRACT, TORT OR OTHERWISE, ARISING FROM,
+OUT OF OR IN CONNECTION WITH THE SOFTWARE OR THE USE OR OTHER DEALINGS IN THE
+SOFTWARE.

connectors/outlook-mail/README.md

@@ -0,0 +1,98 @@
+# Outlook Mail Connector
+
+Syncs Microsoft Outlook mail (personal outlook.com and work/school Microsoft 365
+accounts) into Plot via Microsoft Graph. Each Outlook conversation becomes a
+Plot thread; each message becomes a note on that thread.
+
+## What it syncs
+
+- **Channels** are mail folders (`/me/mailFolders`). Inbox and Sent Items are
+ enabled by default; Junk, Deleted Items, Drafts, Outbox, and Conversation
+ History are never offered. Enabling a folder backfills its history;
+ incremental changes are mailbox-wide (one Graph change-notification
+ subscription on `/me/messages`) and routed to whichever enabled folder the
+ conversation lives in.
+- **Notes** are keyed on `internetMessageId`, so folder moves and the echo of
+ mail sent from Plot dedupe cleanly. Drafts are skipped (Outlook autosave
+ would churn notes).
+- **Attachments** sync as file references and download on demand. Inline
+ images are skipped.
+- **Facets** for Plot's classifier come from RFC 5322 headers (List-Id,
+ Precedence, Auto-Submitted, …) plus Outlook's Focused Inbox
+ (`inferenceClassification`).
+
+## Two-way sync
+
+| Plot action | Outlook effect |
+|---|---|
+| Mark thread read / unread | `isRead` PATCHed on the conversation's messages (unread marks the latest message, read clears all) |
+| Add / remove To Do | `flag.flagStatus` set to `flagged` on the latest message / cleared on all flagged messages |
+| Reply on a thread | Graph `createReply` draft, recipients constrained by the note's access contacts, then sent |
+| New email thread | Graph draft + send, To/CC/BCC from the compose roster |
+
+Outlook-side changes flow back the other way: reading, flagging, replying, and
+new mail all arrive via change notifications (with a 60-minute delta-query
+self-heal catching anything push delivery misses).
+
+## OAuth scopes
+
+| Scope | Why |
+|---|---|
+| `Mail.ReadWrite` | Read folders/messages, update read + flag state, create drafts |
+| `Mail.Send` | Send replies and new mail composed in Plot |
+| `People.Read` | Resolve display names for frequent correspondents who aren't saved contacts |
+| `Contacts.Read` | Resolve display names from saved contacts |
+
+## Known limitations
+
+- **Avatars are not enriched.** Microsoft Graph photo endpoints return
+ auth-gated binary data with no public URL, so there is nothing to store in
+ `contact.avatar`. Contact *names* are enriched from People/Contacts; avatars
+ fall back to Gravatar on the client.
+- **Personal accounts degrade gracefully.** The People API returns limited
+ data for consumer accounts and may 403; enrichment is best-effort per
+ address. Focused Inbox signals are used only when present.
+- Reply bodies are sent as plain text without the quoted-history block (Plot
+ threads already carry the history as notes) — same behavior as the Gmail
+ connector.
+
+## Manual E2E test plan
+
+Prerequisites: the Azure app registration (see `docs/outlook.md` in the core
+repo) must include the delegated scopes `Mail.ReadWrite`, `Mail.Send`,
+`People.Read`, `Contacts.Read`; `AUTH_MICROSOFT_ID`/`AUTH_MICROSOFT_SECRET`
+set in `workers/api/.dev.vars`; tunnel running (`pnpm tunnel:start`) so Graph
+can reach the webhook endpoint (subscriptions are skipped on localhost).
+
+Run the pass twice: once with a **personal** (outlook.com) account and once
+with a **work/school** (Microsoft 365) account.
+
+1. **Connect + channels** — add an Outlook Mail connection; verify the folder
+ list excludes Junk/Deleted/Drafts and defaults Inbox + Sent Items on.
+2. **Backfill** — enable Inbox; verify threads appear with correct titles,
+ per-message notes, participants, timestamps, and that the "Syncing…" badge
+ clears. No unread badges from backfilled mail.
+3. **Inbound incremental** — send mail to the account from outside; verify the
+ thread appears (or extends) within seconds via the subscription.
+4. **Unread round-trip** — read a thread in Plot → message marked read in
+ Outlook; mark a thread unread in Outlook → unread in Plot. Verify no
+ echo loop (state settles after one hop each way).
+5. **Flag ↔ To Do round-trip** — flag in Outlook → thread becomes a Plot
+ To Do; toggle To Do off in Plot → flag cleared in Outlook.
+6. **Reply from Plot** — reply on a synced thread; verify recipients (To/Cc),
+ threading in Outlook, and that the sent message does NOT duplicate as a
+ new note when it syncs back.
+7. **Reply with attachment** — attach a small (<3 MB) and a large (>3 MB)
+ file; verify both arrive in Outlook.
+8. **Compose from Plot** — new email thread to a typed address + a contact
+ with CC; verify delivery, BCC kept out of visible headers, and the
+ originating note binds to the sent message.
+9. **Attachment download** — open a synced message's attachment in Plot.
+10. **Contact names** — verify senders not in the address book still resolve
+ display names where People data exists (work tenant), and degrade to
+ email-only on personal accounts.
+11. **Self-heal** — stop the tunnel for >1 hour, send external mail, restart;
+ verify the hourly delta sweep ingests the missed mail and the
+ subscription is renewed (check `selfHealCheck` log lines).
+12. **Teardown** — disable all folders; verify the Graph subscription is
+ deleted (no further webhook traffic) and re-enabling rebuilds it.

connectors/outlook-mail/package.json

@@ -0,0 +1,48 @@
+{
+ "name": "@plotday/connector-outlook-mail",
+ "plotTwistId": "6c3773dd-e820-4043-a5bc-f4e299ca1a19",
+ "displayName": "Outlook Mail",
+ "description": "Send and reply to Outlook email, tracking threads for follow-up and snoozing the rest.",
+ "category": "messaging",
+ "logoUrl": "https://api.iconify.design/simple-icons/microsoftoutlook.svg",
+ "publisher": "Plot",
+ "publisherUrl": "https://plot.day",
+ "author": "Plot <team@plot.day> (https://plot.day)",
+ "license": "MIT",
+ "version": "0.1.0",
+ "type": "module",
+ "main": "./dist/index.js",
+ "types": "./dist/index.d.ts",
+ "exports": {
+ ".": {
+ "@plotday/connector": "./src/index.ts",
+ "types": "./dist/index.d.ts",
+ "default": "./dist/index.js"
+ }
+ },
+ "private": true,
+ "scripts": {
+ "build": "tsc",
+ "clean": "rm -rf dist",
+ "deploy": "plot deploy",
+ "lint": "plot lint",
+ "test": "vitest run",
+ "test:watch": "vitest"
+ },
+ "dependencies": {
+ "@plotday/email-classifier": "workspace:^",
+ "@plotday/twister": "workspace:^"
+ },
+ "devDependencies": {
+ "typescript": "^5.9.3",
+ "vitest": "^2.1.8"
+ },
+ "repository": {
+ "type": "git",
+ "url": "https://github.com/plotday/plot.git",
+ "directory": "connectors/outlook-mail"
+ },
+ "homepage": "https://plot.day",
+ "bugs": { "url": "https://github.com/plotday/plot/issues" },
+ "keywords": ["plot", "connector", "outlook", "microsoft", "email", "messaging"]
+}

connectors/outlook-mail/src/email-parsing.test.ts

@@ -0,0 +1,24 @@
+import { describe, expect, it } from "vitest";
+import { stripQuotedReply } from "./email-parsing";
+
+describe("stripQuotedReply", () => {
+ it("cuts Outlook appendonsend reply chains", () => {
+ const html = `<div>New content</div><div id="appendonsend"></div><div>From: A<br>Sent: B<br>To: C<br>Subject: D</div>`;
+ expect(stripQuotedReply(html, "html")).toBe("<div>New content</div>");
+ });
+
+ it("cuts gmail_quote blocks from cross-client replies", () => {
+ const html = `<p>Reply</p><div class="gmail_quote">old</div>`;
+ expect(stripQuotedReply(html, "html")).toBe("<p>Reply</p>");
+ });
+
+ it("preserves forwarded messages", () => {
+ const text = "FYI\n---------- Forwarded message ---------\nFrom: x";
+ expect(stripQuotedReply(text, "text")).toBe(text);
+ });
+
+ it("cuts plain-text 'On ... wrote:' quotes", () => {
+ const text = "Thanks!\nOn Tue, Jun 10, 2026, Kris wrote:\n> earlier";
+ expect(stripQuotedReply(text, "text")).toBe("Thanks!");
+ });
+});

connectors/outlook-mail/src/email-parsing.ts

@@ -0,0 +1,153 @@
+// Quote-stripping helpers shared with the Gmail connector (copied from
+// gmail/src/gmail-api.ts — keep in sync).
+
+/**
+ * Locates the start of an Outlook-style "From: / Sent: / To: / Subject:"
+ * reply header even when the field labels are not wrapped in `<b>` or
+ * `<strong>` — e.g. corporate Exchange / Outlook variants that put the
+ * label in a `<span style="font-weight:bold">`, a `<font>` tag, or a
+ * plain `MsoNormal` paragraph with no inline bold at all.
+ *
+ * Strategy: replace every HTML tag with a same-length run of spaces so
+ * character offsets in the stripped text still map 1:1 back to the
+ * original. Then require each label to start at a structural boundary
+ * (start of string, a real newline, or 3+ whitespace chars — the smallest
+ * gap any HTML block tag produces when replaced). That anchor is what
+ * keeps user-written prose from false-matching.
+ *
+ * Returns the index of "From:" in the original content, or -1 if no
+ * Outlook reply header is found.
+ */
+export function findOutlookHeaderTagAgnostic(content: string): number {
+ const flat = content.replace(/<[^>]*>/g, (m) => " ".repeat(m.length));
+ const re =
+ /(?<=^|\n|[ \t]{3,})From:[\s\S]{0,1500}?(?<=\n|[ \t]{3,})Sent:[\s\S]{0,800}?(?<=\n|[ \t]{3,})To:[\s\S]{0,1500}?(?<=\n|[ \t]{3,})Subject:/i;
+ const m = flat.match(re);
+ return m?.index ?? -1;
+}
+
+/**
+ * Strips quoted reply content from an email body.
+ * Since Plot shows each message as a separate note in a thread,
+ * the quoted previous messages are redundant noise.
+ */
+export function stripQuotedReply(
+ content: string,
+ contentType: "text" | "html"
+): string {
+ if (!content) return content;
+
+ // Forwarded messages: the forwarded email IS the content the user wants to
+ // read. Gmail/Apple Mail wrap a forward in the same quote container Gmail uses
+ // for reply quotes, so the reply-stripping below would delete the whole body
+ // and leave an empty note. Keep the content as-is when it's a forward whose
+ // marker precedes any reply boundary.
+ if (isForwardedMessage(content)) return content;
+
+ if (contentType === "html") {
+ // Gmail wraps quoted replies in <div class="gmail_quote">
+ // Remove it and everything after it
+ const gmailQuoteIdx = content.search(
+ /<div[^>]*class\s*=\s*["'][^"']*gmail_quote[^"']*["'][^>]*>/i
+ );
+ if (gmailQuoteIdx !== -1) {
+ return content.substring(0, gmailQuoteIdx).trim();
+ }
+
+ // Some clients use <blockquote> with gmail_quote class
+ const blockquoteIdx = content.search(
+ /<blockquote[^>]*class\s*=\s*["'][^"']*gmail_quote[^"']*["'][^>]*>/i
+ );
+ if (blockquoteIdx !== -1) {
+ return content.substring(0, blockquoteIdx).trim();
+ }
+
+ // Microsoft Outlook-style: <div id="appendonsend"></div> followed by quoted content,
+ // or a <hr> divider followed by "From:" header pattern
+ const outlookDivIdx = content.search(
+ /<div[^>]*id\s*=\s*["'](?:appendonsend|divRplyFwdMsg)["'][^>]*>/i
+ );
+ if (outlookDivIdx !== -1) {
+ return content.substring(0, outlookDivIdx).trim();
+ }
+
+ // Outlook (desktop, OWA, and corporate Exchange clients) wraps replies
+ // with a "From: / Sent: / To: / Subject:" header block. The markup
+ // varies — sometimes `<b>` or `<strong>`, sometimes `<span
+ // style="font-weight:bold">`, sometimes a `MsoNormal` paragraph with
+ // no inline bold at all (Gowling-style corporate Exchange). Try the
+ // tight bold-wrapped pattern first, then fall back to a tag-agnostic
+ // boundary match.
+ const outlookHeaderRe =
+ /<(b|strong)[^>]*>\s*From:?\s*<\/\1>[\s\S]{0,1000}<(b|strong)[^>]*>\s*Sent:?\s*<\/\2>[\s\S]{0,1000}<(b|strong)[^>]*>\s*To:?\s*<\/\3>[\s\S]{0,1000}<(b|strong)[^>]*>\s*Subject:?\s*<\/\4>/i;
+ const outlookHeaderMatch = content.match(outlookHeaderRe);
+ const fromIdx =
+ outlookHeaderMatch?.index ?? findOutlookHeaderTagAgnostic(content);
+ if (fromIdx !== -1) {
+ const lookbackStart = Math.max(0, fromIdx - 1000);
+ const lookback = content.substring(lookbackStart, fromIdx);
+ // Prefer the latest structural divider (border-top div or <hr>)
+ // before the From: tag — that's the user/quoted boundary in
+ // Outlook's standard reply format.
+ const dividerRe =
+ /<hr\b[^>]*>|<div[^>]*style\s*=\s*["'][^"']*border-top\s*:[^"']*["'][^>]*>/gi;
+ let lastDivider = -1;
+ let match: RegExpExecArray | null;
+ while ((match = dividerRe.exec(lookback)) !== null) {
+ lastDivider = match.index;
+ }
+ let cut = fromIdx;
+ if (lastDivider !== -1) {
+ cut = lookbackStart + lastDivider;
+ } else {
+ // No divider — cut at the start of the wrapping <p> or <div>.
+ const lastP = lookback.lastIndexOf("<p");
+ const lastDiv = lookback.lastIndexOf("<div");
+ const wrapper = Math.max(lastP, lastDiv);
+ if (wrapper !== -1) {
+ cut = lookbackStart + wrapper;
+ }
+ }
+ return content.substring(0, cut).trim();
+ }
+
+ return content;
+ }
+
+ // Plain text: look for "On ... wrote:" followed by quoted lines
+ const lines = content.split("\n");
+ for (let i = 0; i < lines.length; i++) {
+ const line = lines[i].trim();
+
+ // "On [date], [name] wrote:" or "On [date], [name] <email> wrote:"
+ if (/^On .+ wrote:\s*$/.test(line)) {
+ // Verify next non-empty line starts with ">" (actual quoted content)
+ const nextContentLine = lines.slice(i + 1).find((l) => l.trim() !== "");
+ if (nextContentLine && nextContentLine.trim().startsWith(">")) {
+ return lines
+ .slice(0, i)
+ .join("\n")
+ .trim();
+ }
+ }
+ }
+
+ return content;
+}
+
+/**
+ * Detects a forwarded message so {@link stripQuotedReply} can preserve it.
+ * Matches Gmail's dashed "---------- Forwarded message ---------" marker and
+ * Apple Mail's "Begin forwarded message:". Returns false when a reply boundary
+ * ("On … wrote:") precedes the forward marker — that's a reply quoting a
+ * forward, which the reply-stripper should still trim.
+ */
+function isForwardedMessage(content: string): boolean {
+ const fwdIdx = content.search(
+ /(-{2,}\s*Forwarded message\s*-{2,}|Begin forwarded message:)/i
+ );
+ if (fwdIdx === -1) return false;
+ const replyIdx = content.search(/On\s[\s\S]{0,200}?\swrote:/i);
+ if (replyIdx !== -1 && replyIdx < fwdIdx) return false;
+ return true;
+}

connectors/outlook-mail/LICENSE

@@ -0,0 +1,21 @@
+MIT License
+
+Copyright (c) 2026 Plot Technologies Inc.
+
+Permission is hereby granted, free of charge, to any person obtaining a copy
+of this software and associated documentation files (the "Software"), to deal
+in the Software without restriction, including without limitation the rights
+to use, copy, modify, merge, publish, distribute, sublicense, and/or sell
+copies of the Software, and to permit persons to whom the Software is
+furnished to do so, subject to the following conditions:
+
+The above copyright notice and this permission notice shall be included in all
+copies or substantial portions of the Software.
+
+THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF ANY KIND, EXPRESS OR
+IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF MERCHANTABILITY,
+FITNESS FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT SHALL THE
+AUTHORS OR COPYRIGHT HOLDERS BE LIABLE FOR ANY CLAIM, DAMAGES OR OTHER
+LIABILITY, WHETHER IN AN ACTION OF CONTRACT, TORT OR OTHERWISE, ARISING FROM,
+OUT OF OR IN CONNECTION WITH THE SOFTWARE OR THE USE OR OTHER DEALINGS IN THE
+SOFTWARE.

connectors/outlook-mail/README.md

@@ -0,0 +1,98 @@
+# Outlook Mail Connector
+
+Syncs Microsoft Outlook mail (personal outlook.com and work/school Microsoft 365
+accounts) into Plot via Microsoft Graph. Each Outlook conversation becomes a
+Plot thread; each message becomes a note on that thread.
+
+## What it syncs
+
+- **Channels** are mail folders (`/me/mailFolders`). Inbox and Sent Items are
+ enabled by default; Junk, Deleted Items, Drafts, Outbox, and Conversation
+ History are never offered. Enabling a folder backfills its history;
+ incremental changes are mailbox-wide (one Graph change-notification
+ subscription on `/me/messages`) and routed to whichever enabled folder the
+ conversation lives in.
+- **Notes** are keyed on `internetMessageId`, so folder moves and the echo of
+ mail sent from Plot dedupe cleanly. Drafts are skipped (Outlook autosave
+ would churn notes).
+- **Attachments** sync as file references and download on demand. Inline
+ images are skipped.
+- **Facets** for Plot's classifier come from RFC 5322 headers (List-Id,
+ Precedence, Auto-Submitted, …) plus Outlook's Focused Inbox
+ (`inferenceClassification`).
+
+## Two-way sync
+
+| Plot action | Outlook effect |
+|---|---|
+| Mark thread read / unread | `isRead` PATCHed on the conversation's messages (unread marks the latest message, read clears all) |
+| Add / remove To Do | `flag.flagStatus` set to `flagged` on the latest message / cleared on all flagged messages |
+| Reply on a thread | Graph `createReply` draft, recipients constrained by the note's access contacts, then sent |
+| New email thread | Graph draft + send, To/CC/BCC from the compose roster |
+
+Outlook-side changes flow back the other way: reading, flagging, replying, and
+new mail all arrive via change notifications (with a 60-minute delta-query
+self-heal catching anything push delivery misses).
+
+## OAuth scopes
+
+| Scope | Why |
+|---|---|
+| `Mail.ReadWrite` | Read folders/messages, update read + flag state, create drafts |
+| `Mail.Send` | Send replies and new mail composed in Plot |
+| `People.Read` | Resolve display names for frequent correspondents who aren't saved contacts |
+| `Contacts.Read` | Resolve display names from saved contacts |
+
+## Known limitations
+
+- **Avatars are not enriched.** Microsoft Graph photo endpoints return
+ auth-gated binary data with no public URL, so there is nothing to store in
+ `contact.avatar`. Contact *names* are enriched from People/Contacts; avatars
+ fall back to Gravatar on the client.
+- **Personal accounts degrade gracefully.** The People API returns limited
+ data for consumer accounts and may 403; enrichment is best-effort per
+ address. Focused Inbox signals are used only when present.
+- Reply bodies are sent as plain text without the quoted-history block (Plot
+ threads already carry the history as notes) — same behavior as the Gmail
+ connector.
+
+## Manual E2E test plan
+
+Prerequisites: the Azure app registration (see `docs/outlook.md` in the core
+repo) must include the delegated scopes `Mail.ReadWrite`, `Mail.Send`,
+`People.Read`, `Contacts.Read`; `AUTH_MICROSOFT_ID`/`AUTH_MICROSOFT_SECRET`
+set in `workers/api/.dev.vars`; tunnel running (`pnpm tunnel:start`) so Graph
+can reach the webhook endpoint (subscriptions are skipped on localhost).
+
+Run the pass twice: once with a **personal** (outlook.com) account and once
+with a **work/school** (Microsoft 365) account.
+
+1. **Connect + channels** — add an Outlook Mail connection; verify the folder
+ list excludes Junk/Deleted/Drafts and defaults Inbox + Sent Items on.
+2. **Backfill** — enable Inbox; verify threads appear with correct titles,
+ per-message notes, participants, timestamps, and that the "Syncing…" badge
+ clears. No unread badges from backfilled mail.
+3. **Inbound incremental** — send mail to the account from outside; verify the
+ thread appears (or extends) within seconds via the subscription.
+4. **Unread round-trip** — read a thread in Plot → message marked read in
+ Outlook; mark a thread unread in Outlook → unread in Plot. Verify no
+ echo loop (state settles after one hop each way).
+5. **Flag ↔ To Do round-trip** — flag in Outlook → thread becomes a Plot
+ To Do; toggle To Do off in Plot → flag cleared in Outlook.
+6. **Reply from Plot** — reply on a synced thread; verify recipients (To/Cc),
+ threading in Outlook, and that the sent message does NOT duplicate as a
+ new note when it syncs back.
+7. **Reply with attachment** — attach a small (<3 MB) and a large (>3 MB)
+ file; verify both arrive in Outlook.
+8. **Compose from Plot** — new email thread to a typed address + a contact
+ with CC; verify delivery, BCC kept out of visible headers, and the
+ originating note binds to the sent message.
+9. **Attachment download** — open a synced message's attachment in Plot.
+10. **Contact names** — verify senders not in the address book still resolve
+ display names where People data exists (work tenant), and degrade to
+ email-only on personal accounts.
+11. **Self-heal** — stop the tunnel for >1 hour, send external mail, restart;
+ verify the hourly delta sweep ingests the missed mail and the
+ subscription is renewed (check `selfHealCheck` log lines).
+12. **Teardown** — disable all folders; verify the Graph subscription is
+ deleted (no further webhook traffic) and re-enabling rebuilds it.

connectors/outlook-mail/package.json

@@ -0,0 +1,48 @@
+{
+ "name": "@plotday/connector-outlook-mail",
+ "plotTwistId": "6c3773dd-e820-4043-a5bc-f4e299ca1a19",
+ "displayName": "Outlook Mail",
+ "description": "Send and reply to Outlook email, tracking threads for follow-up and snoozing the rest.",
+ "category": "messaging",
+ "logoUrl": "https://api.iconify.design/simple-icons/microsoftoutlook.svg",
+ "publisher": "Plot",
+ "publisherUrl": "https://plot.day",
+ "author": "Plot <team@plot.day> (https://plot.day)",
+ "license": "MIT",
+ "version": "0.1.0",
+ "type": "module",
+ "main": "./dist/index.js",
+ "types": "./dist/index.d.ts",
+ "exports": {
+ ".": {
+ "@plotday/connector": "./src/index.ts",
+ "types": "./dist/index.d.ts",
+ "default": "./dist/index.js"
+ }
+ },
+ "private": true,
+ "scripts": {
+ "build": "tsc",
+ "clean": "rm -rf dist",
+ "deploy": "plot deploy",
+ "lint": "plot lint",
+ "test": "vitest run",
+ "test:watch": "vitest"
+ },
+ "dependencies": {
+ "@plotday/email-classifier": "workspace:^",
+ "@plotday/twister": "workspace:^"
+ },
+ "devDependencies": {
+ "typescript": "^5.9.3",
+ "vitest": "^2.1.8"
+ },
+ "repository": {
+ "type": "git",
+ "url": "https://github.com/plotday/plot.git",
+ "directory": "connectors/outlook-mail"
+ },
+ "homepage": "https://plot.day",
+ "bugs": { "url": "https://github.com/plotday/plot/issues" },
+ "keywords": ["plot", "connector", "outlook", "microsoft", "email", "messaging"]
+}

connectors/outlook-mail/src/email-parsing.test.ts

@@ -0,0 +1,24 @@
+import { describe, expect, it } from "vitest";
+import { stripQuotedReply } from "./email-parsing";
+
+describe("stripQuotedReply", () => {
+ it("cuts Outlook appendonsend reply chains", () => {
+ const html = `<div>New content</div><div id="appendonsend"></div><div>From: A<br>Sent: B<br>To: C<br>Subject: D</div>`;
+ expect(stripQuotedReply(html, "html")).toBe("<div>New content</div>");
+ });
+
+ it("cuts gmail_quote blocks from cross-client replies", () => {
+ const html = `<p>Reply</p><div class="gmail_quote">old</div>`;
+ expect(stripQuotedReply(html, "html")).toBe("<p>Reply</p>");
+ });
+
+ it("preserves forwarded messages", () => {
+ const text = "FYI\n---------- Forwarded message ---------\nFrom: x";
+ expect(stripQuotedReply(text, "text")).toBe(text);
+ });
+
+ it("cuts plain-text 'On ... wrote:' quotes", () => {
+ const text = "Thanks!\nOn Tue, Jun 10, 2026, Kris wrote:\n> earlier";
+ expect(stripQuotedReply(text, "text")).toBe("Thanks!");
+ });
+});

connectors/outlook-mail/src/email-parsing.ts

@@ -0,0 +1,153 @@
+// Quote-stripping helpers shared with the Gmail connector (copied from
+// gmail/src/gmail-api.ts — keep in sync).
+
+/**
+ * Locates the start of an Outlook-style "From: / Sent: / To: / Subject:"
+ * reply header even when the field labels are not wrapped in `<b>` or
+ * `<strong>` — e.g. corporate Exchange / Outlook variants that put the
+ * label in a `<span style="font-weight:bold">`, a `<font>` tag, or a
+ * plain `MsoNormal` paragraph with no inline bold at all.
+ *
+ * Strategy: replace every HTML tag with a same-length run of spaces so
+ * character offsets in the stripped text still map 1:1 back to the
+ * original. Then require each label to start at a structural boundary
+ * (start of string, a real newline, or 3+ whitespace chars — the smallest
+ * gap any HTML block tag produces when replaced). That anchor is what
+ * keeps user-written prose from false-matching.
+ *
+ * Returns the index of "From:" in the original content, or -1 if no
+ * Outlook reply header is found.
+ */
+export function findOutlookHeaderTagAgnostic(content: string): number {
+ const flat = content.replace(/<[^>]*>/g, (m) => " ".repeat(m.length));
+ const re =
+ /(?<=^|\n|[ \t]{3,})From:[\s\S]{0,1500}?(?<=\n|[ \t]{3,})Sent:[\s\S]{0,800}?(?<=\n|[ \t]{3,})To:[\s\S]{0,1500}?(?<=\n|[ \t]{3,})Subject:/i;
+ const m = flat.match(re);
+ return m?.index ?? -1;
+}
+
+/**
+ * Strips quoted reply content from an email body.
+ * Since Plot shows each message as a separate note in a thread,
+ * the quoted previous messages are redundant noise.
+ */
+export function stripQuotedReply(
+ content: string,
+ contentType: "text" | "html"
+): string {
+ if (!content) return content;
+
+ // Forwarded messages: the forwarded email IS the content the user wants to
+ // read. Gmail/Apple Mail wrap a forward in the same quote container Gmail uses
+ // for reply quotes, so the reply-stripping below would delete the whole body
+ // and leave an empty note. Keep the content as-is when it's a forward whose
+ // marker precedes any reply boundary.
+ if (isForwardedMessage(content)) return content;
+
+ if (contentType === "html") {
+ // Gmail wraps quoted replies in <div class="gmail_quote">
+ // Remove it and everything after it
+ const gmailQuoteIdx = content.search(
+ /<div[^>]*class\s*=\s*["'][^"']*gmail_quote[^"']*["'][^>]*>/i
+ );
+ if (gmailQuoteIdx !== -1) {
+ return content.substring(0, gmailQuoteIdx).trim();
+ }
+
+ // Some clients use <blockquote> with gmail_quote class
+ const blockquoteIdx = content.search(
+ /<blockquote[^>]*class\s*=\s*["'][^"']*gmail_quote[^"']*["'][^>]*>/i
+ );
+ if (blockquoteIdx !== -1) {
+ return content.substring(0, blockquoteIdx).trim();
+ }
+
+ // Microsoft Outlook-style: <div id="appendonsend"></div> followed by quoted content,
+ // or a <hr> divider followed by "From:" header pattern
+ const outlookDivIdx = content.search(
+ /<div[^>]*id\s*=\s*["'](?:appendonsend|divRplyFwdMsg)["'][^>]*>/i
+ );
+ if (outlookDivIdx !== -1) {
+ return content.substring(0, outlookDivIdx).trim();
+ }
+
+ // Outlook (desktop, OWA, and corporate Exchange clients) wraps replies
+ // with a "From: / Sent: / To: / Subject:" header block. The markup
+ // varies — sometimes `<b>` or `<strong>`, sometimes `<span
+ // style="font-weight:bold">`, sometimes a `MsoNormal` paragraph with
+ // no inline bold at all (Gowling-style corporate Exchange). Try the
+ // tight bold-wrapped pattern first, then fall back to a tag-agnostic
+ // boundary match.
+ const outlookHeaderRe =
+ /<(b|strong)[^>]*>\s*From:?\s*<\/\1>[\s\S]{0,1000}<(b|strong)[^>]*>\s*Sent:?\s*<\/\2>[\s\S]{0,1000}<(b|strong)[^>]*>\s*To:?\s*<\/\3>[\s\S]{0,1000}<(b|strong)[^>]*>\s*Subject:?\s*<\/\4>/i;
+ const outlookHeaderMatch = content.match(outlookHeaderRe);
+ const fromIdx =
+ outlookHeaderMatch?.index ?? findOutlookHeaderTagAgnostic(content);
+ if (fromIdx !== -1) {
+ const lookbackStart = Math.max(0, fromIdx - 1000);
+ const lookback = content.substring(lookbackStart, fromIdx);
+ // Prefer the latest structural divider (border-top div or <hr>)
+ // before the From: tag — that's the user/quoted boundary in
+ // Outlook's standard reply format.
+ const dividerRe =
+ /<hr\b[^>]*>|<div[^>]*style\s*=\s*["'][^"']*border-top\s*:[^"']*["'][^>]*>/gi;
+ let lastDivider = -1;
+ let match: RegExpExecArray | null;
+ while ((match = dividerRe.exec(lookback)) !== null) {
+ lastDivider = match.index;
+ }
+ let cut = fromIdx;
+ if (lastDivider !== -1) {
+ cut = lookbackStart + lastDivider;
+ } else {
+ // No divider — cut at the start of the wrapping <p> or <div>.
+ const lastP = lookback.lastIndexOf("<p");
+ const lastDiv = lookback.lastIndexOf("<div");
+ const wrapper = Math.max(lastP, lastDiv);
+ if (wrapper !== -1) {
+ cut = lookbackStart + wrapper;
+ }
+ }
+ return content.substring(0, cut).trim();
+ }
+
+ return content;
+ }
+
+ // Plain text: look for "On ... wrote:" followed by quoted lines
+ const lines = content.split("\n");
+ for (let i = 0; i < lines.length; i++) {
+ const line = lines[i].trim();
+
+ // "On [date], [name] wrote:" or "On [date], [name] <email> wrote:"
+ if (/^On .+ wrote:\s*$/.test(line)) {
+ // Verify next non-empty line starts with ">" (actual quoted content)
+ const nextContentLine = lines.slice(i + 1).find((l) => l.trim() !== "");
+ if (nextContentLine && nextContentLine.trim().startsWith(">")) {
+ return lines
+ .slice(0, i)
+ .join("\n")
+ .trim();
+ }
+ }
+ }
+
+ return content;
+}
+
+/**
+ * Detects a forwarded message so {@link stripQuotedReply} can preserve it.
+ * Matches Gmail's dashed "---------- Forwarded message ---------" marker and
+ * Apple Mail's "Begin forwarded message:". Returns false when a reply boundary
+ * ("On … wrote:") precedes the forward marker — that's a reply quoting a
+ * forward, which the reply-stripper should still trim.
+ */
+function isForwardedMessage(content: string): boolean {
+ const fwdIdx = content.search(
+ /(-{2,}\s*Forwarded message\s*-{2,}|Begin forwarded message:)/i
+ );
+ if (fwdIdx === -1) return false;
+ const replyIdx = content.search(/On\s[\s\S]{0,200}?\swrote:/i);
+ if (replyIdx !== -1 && replyIdx < fwdIdx) return false;
+ return true;
+}

connectors/outlook-mail/LICENSE

@@ -0,0 +1,21 @@
+MIT License
+
+Copyright (c) 2026 Plot Technologies Inc.
+
+Permission is hereby granted, free of charge, to any person obtaining a copy
+of this software and associated documentation files (the "Software"), to deal
+in the Software without restriction, including without limitation the rights
+to use, copy, modify, merge, publish, distribute, sublicense, and/or sell
+copies of the Software, and to permit persons to whom the Software is
+furnished to do so, subject to the following conditions:
+
+The above copyright notice and this permission notice shall be included in all
+copies or substantial portions of the Software.
+
+THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF ANY KIND, EXPRESS OR
+IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF MERCHANTABILITY,
+FITNESS FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT SHALL THE
+AUTHORS OR COPYRIGHT HOLDERS BE LIABLE FOR ANY CLAIM, DAMAGES OR OTHER
+LIABILITY, WHETHER IN AN ACTION OF CONTRACT, TORT OR OTHERWISE, ARISING FROM,
+OUT OF OR IN CONNECTION WITH THE SOFTWARE OR THE USE OR OTHER DEALINGS IN THE
+SOFTWARE.

connectors/outlook-mail/README.md

@@ -0,0 +1,98 @@
+# Outlook Mail Connector
+
+Syncs Microsoft Outlook mail (personal outlook.com and work/school Microsoft 365
+accounts) into Plot via Microsoft Graph. Each Outlook conversation becomes a
+Plot thread; each message becomes a note on that thread.
+
+## What it syncs
+
+- **Channels** are mail folders (`/me/mailFolders`). Inbox and Sent Items are
+ enabled by default; Junk, Deleted Items, Drafts, Outbox, and Conversation
+ History are never offered. Enabling a folder backfills its history;
+ incremental changes are mailbox-wide (one Graph change-notification
+ subscription on `/me/messages`) and routed to whichever enabled folder the
+ conversation lives in.
+- **Notes** are keyed on `internetMessageId`, so folder moves and the echo of
+ mail sent from Plot dedupe cleanly. Drafts are skipped (Outlook autosave
+ would churn notes).
+- **Attachments** sync as file references and download on demand. Inline
+ images are skipped.
+- **Facets** for Plot's classifier come from RFC 5322 headers (List-Id,
+ Precedence, Auto-Submitted, …) plus Outlook's Focused Inbox
+ (`inferenceClassification`).
+
+## Two-way sync
+
+| Plot action | Outlook effect |
+|---|---|
+| Mark thread read / unread | `isRead` PATCHed on the conversation's messages (unread marks the latest message, read clears all) |
+| Add / remove To Do | `flag.flagStatus` set to `flagged` on the latest message / cleared on all flagged messages |
+| Reply on a thread | Graph `createReply` draft, recipients constrained by the note's access contacts, then sent |
+| New email thread | Graph draft + send, To/CC/BCC from the compose roster |
+
+Outlook-side changes flow back the other way: reading, flagging, replying, and
+new mail all arrive via change notifications (with a 60-minute delta-query
+self-heal catching anything push delivery misses).
+
+## OAuth scopes
+
+| Scope | Why |
+|---|---|
+| `Mail.ReadWrite` | Read folders/messages, update read + flag state, create drafts |
+| `Mail.Send` | Send replies and new mail composed in Plot |
+| `People.Read` | Resolve display names for frequent correspondents who aren't saved contacts |
+| `Contacts.Read` | Resolve display names from saved contacts |
+
+## Known limitations
+
+- **Avatars are not enriched.** Microsoft Graph photo endpoints return
+ auth-gated binary data with no public URL, so there is nothing to store in
+ `contact.avatar`. Contact *names* are enriched from People/Contacts; avatars
+ fall back to Gravatar on the client.
+- **Personal accounts degrade gracefully.** The People API returns limited
+ data for consumer accounts and may 403; enrichment is best-effort per
+ address. Focused Inbox signals are used only when present.
+- Reply bodies are sent as plain text without the quoted-history block (Plot
+ threads already carry the history as notes) — same behavior as the Gmail
+ connector.
+
+## Manual E2E test plan
+
+Prerequisites: the Azure app registration (see `docs/outlook.md` in the core
+repo) must include the delegated scopes `Mail.ReadWrite`, `Mail.Send`,
+`People.Read`, `Contacts.Read`; `AUTH_MICROSOFT_ID`/`AUTH_MICROSOFT_SECRET`
+set in `workers/api/.dev.vars`; tunnel running (`pnpm tunnel:start`) so Graph
+can reach the webhook endpoint (subscriptions are skipped on localhost).
+
+Run the pass twice: once with a **personal** (outlook.com) account and once
+with a **work/school** (Microsoft 365) account.
+
+1. **Connect + channels** — add an Outlook Mail connection; verify the folder
+ list excludes Junk/Deleted/Drafts and defaults Inbox + Sent Items on.
+2. **Backfill** — enable Inbox; verify threads appear with correct titles,
+ per-message notes, participants, timestamps, and that the "Syncing…" badge
+ clears. No unread badges from backfilled mail.
+3. **Inbound incremental** — send mail to the account from outside; verify the
+ thread appears (or extends) within seconds via the subscription.
+4. **Unread round-trip** — read a thread in Plot → message marked read in
+ Outlook; mark a thread unread in Outlook → unread in Plot. Verify no
+ echo loop (state settles after one hop each way).
+5. **Flag ↔ To Do round-trip** — flag in Outlook → thread becomes a Plot
+ To Do; toggle To Do off in Plot → flag cleared in Outlook.
+6. **Reply from Plot** — reply on a synced thread; verify recipients (To/Cc),
+ threading in Outlook, and that the sent message does NOT duplicate as a
+ new note when it syncs back.
+7. **Reply with attachment** — attach a small (<3 MB) and a large (>3 MB)
+ file; verify both arrive in Outlook.
+8. **Compose from Plot** — new email thread to a typed address + a contact
+ with CC; verify delivery, BCC kept out of visible headers, and the
+ originating note binds to the sent message.
+9. **Attachment download** — open a synced message's attachment in Plot.
+10. **Contact names** — verify senders not in the address book still resolve
+ display names where People data exists (work tenant), and degrade to
+ email-only on personal accounts.
+11. **Self-heal** — stop the tunnel for >1 hour, send external mail, restart;
+ verify the hourly delta sweep ingests the missed mail and the
+ subscription is renewed (check `selfHealCheck` log lines).
+12. **Teardown** — disable all folders; verify the Graph subscription is
+ deleted (no further webhook traffic) and re-enabling rebuilds it.

connectors/outlook-mail/package.json

@@ -0,0 +1,48 @@
+{
+ "name": "@plotday/connector-outlook-mail",
+ "plotTwistId": "6c3773dd-e820-4043-a5bc-f4e299ca1a19",
+ "displayName": "Outlook Mail",
+ "description": "Send and reply to Outlook email, tracking threads for follow-up and snoozing the rest.",
+ "category": "messaging",
+ "logoUrl": "https://api.iconify.design/simple-icons/microsoftoutlook.svg",
+ "publisher": "Plot",
+ "publisherUrl": "https://plot.day",
+ "author": "Plot <team@plot.day> (https://plot.day)",
+ "license": "MIT",
+ "version": "0.1.0",
+ "type": "module",
+ "main": "./dist/index.js",
+ "types": "./dist/index.d.ts",
+ "exports": {
+ ".": {
+ "@plotday/connector": "./src/index.ts",
+ "types": "./dist/index.d.ts",
+ "default": "./dist/index.js"
+ }
+ },
+ "private": true,
+ "scripts": {
+ "build": "tsc",
+ "clean": "rm -rf dist",
+ "deploy": "plot deploy",
+ "lint": "plot lint",
+ "test": "vitest run",
+ "test:watch": "vitest"
+ },
+ "dependencies": {
+ "@plotday/email-classifier": "workspace:^",
+ "@plotday/twister": "workspace:^"
+ },
+ "devDependencies": {
+ "typescript": "^5.9.3",
+ "vitest": "^2.1.8"
+ },
+ "repository": {
+ "type": "git",
+ "url": "https://github.com/plotday/plot.git",
+ "directory": "connectors/outlook-mail"
+ },
+ "homepage": "https://plot.day",
+ "bugs": { "url": "https://github.com/plotday/plot/issues" },
+ "keywords": ["plot", "connector", "outlook", "microsoft", "email", "messaging"]
+}

connectors/outlook-mail/src/email-parsing.test.ts

@@ -0,0 +1,24 @@
+import { describe, expect, it } from "vitest";
+import { stripQuotedReply } from "./email-parsing";
+
+describe("stripQuotedReply", () => {
+ it("cuts Outlook appendonsend reply chains", () => {
+ const html = `<div>New content</div><div id="appendonsend"></div><div>From: A<br>Sent: B<br>To: C<br>Subject: D</div>`;
+ expect(stripQuotedReply(html, "html")).toBe("<div>New content</div>");
+ });
+
+ it("cuts gmail_quote blocks from cross-client replies", () => {
+ const html = `<p>Reply</p><div class="gmail_quote">old</div>`;
+ expect(stripQuotedReply(html, "html")).toBe("<p>Reply</p>");
+ });
+
+ it("preserves forwarded messages", () => {
+ const text = "FYI\n---------- Forwarded message ---------\nFrom: x";
+ expect(stripQuotedReply(text, "text")).toBe(text);
+ });
+
+ it("cuts plain-text 'On ... wrote:' quotes", () => {
+ const text = "Thanks!\nOn Tue, Jun 10, 2026, Kris wrote:\n> earlier";
+ expect(stripQuotedReply(text, "text")).toBe("Thanks!");
+ });
+});

connectors/outlook-mail/src/email-parsing.ts

@@ -0,0 +1,153 @@
+// Quote-stripping helpers shared with the Gmail connector (copied from
+// gmail/src/gmail-api.ts — keep in sync).
+
+/**
+ * Locates the start of an Outlook-style "From: / Sent: / To: / Subject:"
+ * reply header even when the field labels are not wrapped in `<b>` or
+ * `<strong>` — e.g. corporate Exchange / Outlook variants that put the
+ * label in a `<span style="font-weight:bold">`, a `<font>` tag, or a
+ * plain `MsoNormal` paragraph with no inline bold at all.
+ *
+ * Strategy: replace every HTML tag with a same-length run of spaces so
+ * character offsets in the stripped text still map 1:1 back to the
+ * original. Then require each label to start at a structural boundary
+ * (start of string, a real newline, or 3+ whitespace chars — the smallest
+ * gap any HTML block tag produces when replaced). That anchor is what
+ * keeps user-written prose from false-matching.
+ *
+ * Returns the index of "From:" in the original content, or -1 if no
+ * Outlook reply header is found.
+ */
+export function findOutlookHeaderTagAgnostic(content: string): number {
+ const flat = content.replace(/<[^>]*>/g, (m) => " ".repeat(m.length));
+ const re =
+ /(?<=^|\n|[ \t]{3,})From:[\s\S]{0,1500}?(?<=\n|[ \t]{3,})Sent:[\s\S]{0,800}?(?<=\n|[ \t]{3,})To:[\s\S]{0,1500}?(?<=\n|[ \t]{3,})Subject:/i;
+ const m = flat.match(re);
+ return m?.index ?? -1;
+}
+
+/**
+ * Strips quoted reply content from an email body.
+ * Since Plot shows each message as a separate note in a thread,
+ * the quoted previous messages are redundant noise.
+ */
+export function stripQuotedReply(
+ content: string,
+ contentType: "text" | "html"
+): string {
+ if (!content) return content;
+
+ // Forwarded messages: the forwarded email IS the content the user wants to
+ // read. Gmail/Apple Mail wrap a forward in the same quote container Gmail uses
+ // for reply quotes, so the reply-stripping below would delete the whole body
+ // and leave an empty note. Keep the content as-is when it's a forward whose
+ // marker precedes any reply boundary.
+ if (isForwardedMessage(content)) return content;
+
+ if (contentType === "html") {
+ // Gmail wraps quoted replies in <div class="gmail_quote">
+ // Remove it and everything after it
+ const gmailQuoteIdx = content.search(
+ /<div[^>]*class\s*=\s*["'][^"']*gmail_quote[^"']*["'][^>]*>/i
+ );
+ if (gmailQuoteIdx !== -1) {
+ return content.substring(0, gmailQuoteIdx).trim();
+ }
+
+ // Some clients use <blockquote> with gmail_quote class
+ const blockquoteIdx = content.search(
+ /<blockquote[^>]*class\s*=\s*["'][^"']*gmail_quote[^"']*["'][^>]*>/i
+ );
+ if (blockquoteIdx !== -1) {
+ return content.substring(0, blockquoteIdx).trim();
+ }
+
+ // Microsoft Outlook-style: <div id="appendonsend"></div> followed by quoted content,
+ // or a <hr> divider followed by "From:" header pattern
+ const outlookDivIdx = content.search(
+ /<div[^>]*id\s*=\s*["'](?:appendonsend|divRplyFwdMsg)["'][^>]*>/i
+ );
+ if (outlookDivIdx !== -1) {
+ return content.substring(0, outlookDivIdx).trim();
+ }
+
+ // Outlook (desktop, OWA, and corporate Exchange clients) wraps replies
+ // with a "From: / Sent: / To: / Subject:" header block. The markup
+ // varies — sometimes `<b>` or `<strong>`, sometimes `<span
+ // style="font-weight:bold">`, sometimes a `MsoNormal` paragraph with
+ // no inline bold at all (Gowling-style corporate Exchange). Try the
+ // tight bold-wrapped pattern first, then fall back to a tag-agnostic
+ // boundary match.
+ const outlookHeaderRe =
+ /<(b|strong)[^>]*>\s*From:?\s*<\/\1>[\s\S]{0,1000}<(b|strong)[^>]*>\s*Sent:?\s*<\/\2>[\s\S]{0,1000}<(b|strong)[^>]*>\s*To:?\s*<\/\3>[\s\S]{0,1000}<(b|strong)[^>]*>\s*Subject:?\s*<\/\4>/i;
+ const outlookHeaderMatch = content.match(outlookHeaderRe);
+ const fromIdx =
+ outlookHeaderMatch?.index ?? findOutlookHeaderTagAgnostic(content);
+ if (fromIdx !== -1) {
+ const lookbackStart = Math.max(0, fromIdx - 1000);
+ const lookback = content.substring(lookbackStart, fromIdx);
+ // Prefer the latest structural divider (border-top div or <hr>)
+ // before the From: tag — that's the user/quoted boundary in
+ // Outlook's standard reply format.
+ const dividerRe =
+ /<hr\b[^>]*>|<div[^>]*style\s*=\s*["'][^"']*border-top\s*:[^"']*["'][^>]*>/gi;
+ let lastDivider = -1;
+ let match: RegExpExecArray | null;
+ while ((match = dividerRe.exec(lookback)) !== null) {
+ lastDivider = match.index;
+ }
+ let cut = fromIdx;
+ if (lastDivider !== -1) {
+ cut = lookbackStart + lastDivider;
+ } else {
+ // No divider — cut at the start of the wrapping <p> or <div>.
+ const lastP = lookback.lastIndexOf("<p");
+ const lastDiv = lookback.lastIndexOf("<div");
+ const wrapper = Math.max(lastP, lastDiv);
+ if (wrapper !== -1) {
+ cut = lookbackStart + wrapper;
+ }
+ }
+ return content.substring(0, cut).trim();
+ }
+
+ return content;
+ }
+
+ // Plain text: look for "On ... wrote:" followed by quoted lines
+ const lines = content.split("\n");
+ for (let i = 0; i < lines.length; i++) {
+ const line = lines[i].trim();
+
+ // "On [date], [name] wrote:" or "On [date], [name] <email> wrote:"
+ if (/^On .+ wrote:\s*$/.test(line)) {
+ // Verify next non-empty line starts with ">" (actual quoted content)
+ const nextContentLine = lines.slice(i + 1).find((l) => l.trim() !== "");
+ if (nextContentLine && nextContentLine.trim().startsWith(">")) {
+ return lines
+ .slice(0, i)
+ .join("\n")
+ .trim();
+ }
+ }
+ }
+
+ return content;
+}
+
+/**
+ * Detects a forwarded message so {@link stripQuotedReply} can preserve it.
+ * Matches Gmail's dashed "---------- Forwarded message ---------" marker and
+ * Apple Mail's "Begin forwarded message:". Returns false when a reply boundary
+ * ("On … wrote:") precedes the forward marker — that's a reply quoting a
+ * forward, which the reply-stripper should still trim.
+ */
+function isForwardedMessage(content: string): boolean {
+ const fwdIdx = content.search(
+ /(-{2,}\s*Forwarded message\s*-{2,}|Begin forwarded message:)/i
+ );
+ if (fwdIdx === -1) return false;
+ const replyIdx = content.search(/On\s[\s\S]{0,200}?\swrote:/i);
+ if (replyIdx !== -1 && replyIdx < fwdIdx) return false;
+ return true;
+}