fix(connectors): render note Markdown for outbound email & chat#219

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Merged
KrisBraun merged 2 commits into from
Jun 23, 2026
Merged

fix(connectors): render note Markdown for outbound email & chat #219

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5b86390
fix(connectors): render note Markdown for outbound email & chat
KrisBraun Jun 23, 2026
a957964
chore: update lockfile for marked dependency
KrisBraun Jun 23, 2026
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5 changes: 5 additions & 0 deletions .changeset/email-markdown-html.md
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Original file line numberDiff line numberDiff line change
@@ -0,0 +1,5 @@
---
"@plotday/twister": minor
---

Added: `markdownToHtml` (`@plotday/twister/utils/markdown-html`) — renders Plot Markdown note content to an HTML email fragment (mentions become `@Name`, GFM with `breaks`). Used by email connectors to send rich HTML bodies instead of raw Markdown as `text/plain`.
108 changes: 108 additions & 0 deletions connectors/gmail/src/gmail-api.test.ts
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Original file line numberDiff line numberDiff line change
@@ -1,12 +1,34 @@
import { describe, expect, it } from "vitest";
import {
buildNewEmailMessage,
buildReplyMessage,
stripQuotedReply,
transformGmailThread,
type AttachmentData,
type GmailMessage,
type GmailMessagePart,
type GmailThread,
} from "./gmail-api";

/** Decode the base64url raw message the Gmail send API would receive. */
function decodeRawMessage(b64url: string): string {
const b64 = b64url.replace(/-/g, "+").replace(/_/g, "/");
return Buffer.from(b64, "base64").toString("utf8");
}

/** Decode the base64 body of the first MIME part declaring `mimeType`. */
function decodeMimePart(raw: string, mimeType: string): string {
const segments = raw.split(/\r\n--[^\r\n]+(?:--)?\r\n?/);
for (const seg of segments) {
if (!seg.includes(`Content-Type: ${mimeType}`)) continue;
const blank = seg.indexOf("\r\n\r\n");
if (blank === -1) continue;
const b64 = seg.slice(blank + 4).replace(/\r\n/g, "").trim();
return Buffer.from(b64, "base64").toString("utf8");
}
return "";
}

// Gmail API returns part bodies as base64url. Encode fixtures the same way the
// real API does so `extractBody`'s atob/replace decode path is exercised.
function b64url(s: string): string {
Expand DownExpand Up@@ -171,3 +193,89 @@ describe("forwarded email body extraction", () => {
expect(reply).not.toContain("old message text");
});
});

describe("outbound MIME bodies (multipart/alternative HTML + plain)", () => {
const markdownBody =
"**Exploring burnout**\n\n" +
"Is burnout caused by too much work? I think either could work, " +
"and the key will be positioning and messaging for our first session.";

it("buildReplyMessage emits multipart/alternative with text and html parts", () => {
const raw = decodeRawMessage(
buildReplyMessage({
to: ["phil467@gmail.com"],
cc: ["kris@plot.day"],
from: "beth@plot.day",
subject: "Workshop ideas",
body: markdownBody,
messageId: "<abc@mail.gmail.com>",
references: "<root@mail.gmail.com>",
})
);

expect(raw).toContain("Content-Type: multipart/alternative");
expect(raw).toContain('Content-Type: text/plain; charset="UTF-8"');
expect(raw).toContain('Content-Type: text/html; charset="UTF-8"');

// HTML part renders markdown (no literal ** asterisks reach the reader).
const html = decodeMimePart(raw, "text/html");
expect(html).toContain("<strong>Exploring burnout</strong>");
expect(html).not.toContain("**Exploring burnout**");

// Plain part is clean text — markdown syntax stripped, sentence intact on
// one logical line (no hard mid-sentence wrap that the recipient would see).
const text = decodeMimePart(raw, "text/plain");
expect(text).toContain("Exploring burnout");
expect(text).not.toContain("**");
expect(text).toContain(
"Is burnout caused by too much work? I think either could work, and the key will be positioning and messaging for our first session."
);
});

it("buildReplyMessage with attachments nests alternative inside multipart/mixed", () => {
const attachments: AttachmentData[] = [
{
fileName: "notes.txt",
mimeType: "text/plain",
data: new TextEncoder().encode("hello"),
},
];
const raw = decodeRawMessage(
buildReplyMessage({
to: ["phil467@gmail.com"],
cc: [],
from: "beth@plot.day",
subject: "Workshop ideas",
body: markdownBody,
messageId: "<abc@mail.gmail.com>",
references: "",
attachments,
})
);

expect(raw).toContain("Content-Type: multipart/mixed");
expect(raw).toContain("Content-Type: multipart/alternative");
expect(raw).toContain('Content-Type: text/html; charset="UTF-8"');
expect(raw).toContain('Content-Disposition: attachment; filename="notes.txt"');
expect(decodeMimePart(raw, "text/html")).toContain(
"<strong>Exploring burnout</strong>"
);
});

it("buildNewEmailMessage emits multipart/alternative with text and html parts", () => {
const raw = decodeRawMessage(
buildNewEmailMessage({
to: ["phil467@gmail.com"],
from: "beth@plot.day",
subject: "Workshop ideas",
body: markdownBody,
})
);

expect(raw).toContain("Content-Type: multipart/alternative");
expect(decodeMimePart(raw, "text/html")).toContain(
"<strong>Exploring burnout</strong>"
);
expect(decodeMimePart(raw, "text/plain")).not.toContain("**");
});
});
187 changes: 101 additions & 86 deletions connectors/gmail/src/gmail-api.ts
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Original file line numberDiff line numberDiff line change
Expand Up@@ -5,6 +5,8 @@ import type {
NewContact,
Action,
} from "@plotday/twister/plot";
import { markdownToPlainText } from "@plotday/twister/utils/markdown";
import { markdownToHtml } from "@plotday/twister/utils/markdown-html";


export type GmailLabel = {
Expand DownExpand Up@@ -1135,19 +1137,17 @@ export function buildNewEmailMessage(options: {
}

lines.push(`Subject: ${sanitizeHeaderValue(subject)}`);
lines.push(`Content-Type: text/plain; charset="UTF-8"`);
lines.push(""); // Empty line separates headers from body
lines.push(body);
lines.push(`MIME-Version: 1.0`);

const rawMessage = lines.join("\r\n");
// Body is a multipart/alternative (plain text + rendered HTML) so recipients
// get clean formatting instead of raw Markdown wrapped by their mail server.
const altBoundary = mimeBoundary("alt");
const rawMessage = [
...lines,
...buildAlternativeBlock(altBoundary, body),
].join("\r\n");

// Base64url encode
return btoa(
String.fromCharCode(...new TextEncoder().encode(rawMessage))
)
.replace(/\+/g, "-")
.replace(/\//g, "_")
.replace(/=+$/, "");
return base64UrlEncodeMessage(rawMessage);
}

/**
Expand All@@ -1173,6 +1173,67 @@ function uint8ArrayToBase64Lines(bytes: Uint8Array): string {
return lines.join("\r\n");
}

/** Generate a unique MIME multipart boundary with the given role suffix. */
function mimeBoundary(role: string): string {
return `----=_PlotBoundary_${role}_${Date.now().toString(16)}`;
}

/** base64url-encode an RFC 2822 raw message for the Gmail send API. Chunked to
* avoid `String.fromCharCode(...bytes)` stack overflow on large bodies. */
function base64UrlEncodeMessage(rawMessage: string): string {
const msgBytes = new TextEncoder().encode(rawMessage);
const CHUNK = 32768;
let binary = "";
for (let i = 0; i < msgBytes.length; i += CHUNK) {
const slice = msgBytes.subarray(i, i + CHUNK);
for (let j = 0; j < slice.length; j++) {
binary += String.fromCharCode(slice[j]);
}
}
return btoa(binary)
.replace(/\+/g, "-")
.replace(/\//g, "_")
.replace(/=+$/, "");
}

/**
* Build the lines of a `multipart/alternative` MIME entity (including its own
* `Content-Type` header) carrying the note body as two parts: a clean
* `text/plain` fallback (Markdown stripped to plain text, no hard column
* wrapping) and a rendered `text/html` part.
*
* Sending both — instead of raw Markdown as a bare `text/plain` body — stops
* the recipient's mail server from hard-wrapping prose mid-sentence and lets
* formatting (bold, links, lists) render. Both parts are base64-encoded so the
* declared `Content-Transfer-Encoding` matches the emitted bytes.
*
* The returned lines begin with the `Content-Type: multipart/alternative`
* header, so the caller can place them directly after the message headers (as
* the top-level body) or after a `multipart/mixed` boundary (nested alongside
* attachments).
*/
function buildAlternativeBlock(altBoundary: string, body: string): string[] {
const text = markdownToPlainText(body);
const htmlFragment = markdownToHtml(body);
const html = `<!DOCTYPE html>\r\n<html><body>\r\n${htmlFragment}\r\n</body></html>`;
const enc = new TextEncoder();
return [
`Content-Type: multipart/alternative; boundary="${altBoundary}"`,
"",
`--${altBoundary}`,
`Content-Type: text/plain; charset="UTF-8"`,
`Content-Transfer-Encoding: base64`,
"",
uint8ArrayToBase64Lines(enc.encode(text)),
`--${altBoundary}`,
`Content-Type: text/html; charset="UTF-8"`,
`Content-Transfer-Encoding: base64`,
"",
uint8ArrayToBase64Lines(enc.encode(html)),
`--${altBoundary}--`,
];
}

/**
* Attachment data for building MIME messages.
*/
Expand DownExpand Up@@ -1211,47 +1272,35 @@ export function buildReplyMessage(options: {
subject.startsWith("Re:") ? subject : `Re: ${subject}`
);

// Shared headers for both the attachment and no-attachment paths.
const headerLines: string[] = [`From: ${fromHeader}`, `To: ${toHeader}`];
if (cc.length > 0) headerLines.push(`Cc: ${ccHeader}`);
headerLines.push(`Subject: ${reSubject}`);
headerLines.push(`In-Reply-To: ${safeMessageId}`);
const refChain = safeReferences
? `${safeReferences} ${safeMessageId}`
: safeMessageId;
headerLines.push(`References: ${refChain}`);
headerLines.push(`MIME-Version: 1.0`);

// The body is always a multipart/alternative (plain text + rendered HTML) so
// recipients get clean formatting and MTAs don't hard-wrap raw Markdown.
const altBoundary = mimeBoundary("alt");
const altBlock = buildAlternativeBlock(altBoundary, body);

let rawMessage: string;

if (attachments && attachments.length > 0) {
// Build multipart/mixed message with text body + attachment parts
const boundary = `----=_PlotBoundary_${Date.now().toString(16)}`;

const headerLines: string[] = [
`From: ${fromHeader}`,
`To: ${toHeader}`,
];
if (cc.length > 0) headerLines.push(`Cc: ${ccHeader}`);
headerLines.push(`Subject: ${reSubject}`);
headerLines.push(`In-Reply-To: ${safeMessageId}`);
const refChain = safeReferences
? `${safeReferences} ${safeMessageId}`
: safeMessageId;
headerLines.push(`References: ${refChain}`);
headerLines.push(`MIME-Version: 1.0`);
headerLines.push(`Content-Type: multipart/mixed; boundary="${boundary}"`);
headerLines.push(""); // end of headers

// Text body part. Base64-encode the UTF-8 body so the declared
// Content-Transfer-Encoding matches the bytes we emit — inserting a raw
// 8-bit body under a `quoted-printable` (or any non-identity) declaration
// corrupts non-ASCII content and breaks strict MIME parsers.
const bodyPart = [
`--${boundary}`,
`Content-Type: text/plain; charset="UTF-8"`,
`Content-Transfer-Encoding: base64`,
"",
uint8ArrayToBase64Lines(new TextEncoder().encode(body)),
];
// Wrap the alternative body and the attachments in a multipart/mixed.
const mixBoundary = mimeBoundary("mix");

// Attachment parts
const attachmentParts: string[] = [];
for (const att of attachments) {
const b64Lines = uint8ArrayToBase64Lines(att.data);
// Encode filename for Content-Disposition
const safeFileName = att.fileName.replace(/[\r\n"]/g, "_");
attachmentParts.push(
`--${boundary}`,
`--${mixBoundary}`,
`Content-Type: ${att.mimeType}; name="${safeFileName}"`,
`Content-Transfer-Encoding: base64`,
`Content-Disposition: attachment; filename="${safeFileName}"`,
Expand All@@ -1261,52 +1310,18 @@ export function buildReplyMessage(options: {
}

rawMessage = [
headerLines.join("\r\n"),
bodyPart.join("\r\n"),
...attachmentParts.map((p) => p),
`--${boundary}--`,
...headerLines,
`Content-Type: multipart/mixed; boundary="${mixBoundary}"`,
"", // end of message headers
`--${mixBoundary}`,
...altBlock,
...attachmentParts,
`--${mixBoundary}--`,
].join("\r\n");
} else {
// Simple text-only message (existing path)
const lines: string[] = [
`From: ${fromHeader}`,
`To: ${toHeader}`,
];

if (cc.length > 0) {
lines.push(`Cc: ${ccHeader}`);
}

lines.push(`Subject: ${reSubject}`);
lines.push(`In-Reply-To: ${safeMessageId}`);

// Build References chain
const refChain = safeReferences
? `${safeReferences} ${safeMessageId}`
: safeMessageId;
lines.push(`References: ${refChain}`);

lines.push(`Content-Type: text/plain; charset="UTF-8"`);
lines.push(""); // Empty line separates headers from body
lines.push(body);

rawMessage = lines.join("\r\n");
}

// Base64url encode the entire raw message
const msgBytes = new TextEncoder().encode(rawMessage);
const CHUNK = 32768;
let binary = "";
for (let i = 0; i < msgBytes.length; i += CHUNK) {
const slice = msgBytes.subarray(i, i + CHUNK);
for (let j = 0; j < slice.length; j++) {
binary += String.fromCharCode(slice[j]);
}
// Top-level body is the multipart/alternative entity itself.
rawMessage = [...headerLines, ...altBlock].join("\r\n");
}
const encoded = btoa(binary)
.replace(/\+/g, "-")
.replace(/\//g, "_")
.replace(/=+$/, "");

return encoded;
return base64UrlEncodeMessage(rawMessage);
}
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, 'i'); if (__m === '*' || __re.test(location.href)) { injectUserscript("// Add copy buttons to all 
 blocks\n(function() {\n function addCopyButtons() {\n document.querySelectorAll('pre code').forEach(function(codeBlock) {\n if (codeBlock.parentElement.hasAttribute('data-copy-added')) return;\n codeBlock.parentElement.setAttribute('data-copy-added', 'true');\n \n var btn = document.createElement('button');\n btn.textContent = 'Copy';\n btn.style.cssText = 'position:absolute;top:4px;right:4px;padding:2px 8px;font-size:11px;background:#4ecdc4;border:none;border-radius:4px;color:#1a1a2e;cursor:pointer;opacity:0.7;transition:opacity 0.2s;';\n btn.onmouseover = function() { this.style.opacity = '1'; };\n btn.onmouseout = function() { this.style.opacity = '0.7'; };\n btn.onclick = function() {\n navigator.clipboard.writeText(codeBlock.textContent).then(function() {\n btn.textContent = 'Copied!';\n setTimeout(function() { btn.textContent = 'Copy'; }, 1500);\n });\n };\n codeBlock.parentElement.style.position = 'relative';\n codeBlock.parentElement.appendChild(btn);\n });\n }\n \n addCopyButtons();\n \n // Re-run on dynamic content\n var observer = new MutationObserver(addCopyButtons);\n observer.observe(document.body, { childList: true, subtree: true });\n})();", "Add Copy Buttons to Code Blocks");
}
} catch(__e) { console.warn('[Userscript:Add Copy Buttons to Code Blocks]', __e); }
})();
(function(){
try {
var __m = "github.com";
var __re = new RegExp('^' + "github\\.com" + '

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fix(connectors): render note Markdown for outbound email & chat#219

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 Merged

KrisBraun
merged 2 commits into

from

Jun 23, 2026
 Merged


fix(connectors): render note Markdown for outbound email & chat
#219
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5b86390

fix(connectors): render note Markdown for outbound email & chat


KrisBraun Jun 23, 2026
a957964

chore: update lockfile for marked dependency


KrisBraun Jun 23, 2026

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5 changes: 5 additions & 0 deletions
.changeset/email-markdown-html.md

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Original file line numberDiff line numberDiff line change
@@ -0,0 +1,5 @@
---
"@plotday/twister": minor
---

Added: `markdownToHtml` (`@plotday/twister/utils/markdown-html`) — renders Plot Markdown note content to an HTML email fragment (mentions become `@Name`, GFM with `breaks`). Used by email connectors to send rich HTML bodies instead of raw Markdown as `text/plain`.

108 changes: 108 additions & 0 deletions
connectors/gmail/src/gmail-api.test.ts

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Original file line numberDiff line numberDiff line change
@@ -1,12 +1,34 @@
import { describe, expect, it } from "vitest";
import {
 buildNewEmailMessage,
 buildReplyMessage,
 stripQuotedReply,
 transformGmailThread,
 type AttachmentData,
 type GmailMessage,
 type GmailMessagePart,
 type GmailThread,
} from "./gmail-api";

/** Decode the base64url raw message the Gmail send API would receive. */
function decodeRawMessage(b64url: string): string {
 const b64 = b64url.replace(/-/g, "+").replace(/_/g, "/");
 return Buffer.from(b64, "base64").toString("utf8");
}

/** Decode the base64 body of the first MIME part declaring `mimeType`. */
function decodeMimePart(raw: string, mimeType: string): string {
 const segments = raw.split(/\r\n--[^\r\n]+(?:--)?\r\n?/);
 for (const seg of segments) {
 if (!seg.includes(`Content-Type: ${mimeType}`)) continue;
 const blank = seg.indexOf("\r\n\r\n");
 if (blank === -1) continue;
 const b64 = seg.slice(blank + 4).replace(/\r\n/g, "").trim();
 return Buffer.from(b64, "base64").toString("utf8");
 }
 return "";
}

// Gmail API returns part bodies as base64url. Encode fixtures the same way the
// real API does so `extractBody`'s atob/replace decode path is exercised.
function b64url(s: string): string {
Expand DownExpand Up@@ -171,3 +193,89 @@ describe("forwarded email body extraction", () => {
 expect(reply).not.toContain("old message text");
 });
});

describe("outbound MIME bodies (multipart/alternative HTML + plain)", () => {
 const markdownBody =
 "**Exploring burnout**\n\n" +
 "Is burnout caused by too much work? I think either could work, " +
 "and the key will be positioning and messaging for our first session.";

 it("buildReplyMessage emits multipart/alternative with text and html parts", () => {
 const raw = decodeRawMessage(
 buildReplyMessage({
 to: ["phil467@gmail.com"],
 cc: ["kris@plot.day"],
 from: "beth@plot.day",
 subject: "Workshop ideas",
 body: markdownBody,
 messageId: "<abc@mail.gmail.com>",
 references: "<root@mail.gmail.com>",
 })
 );

 expect(raw).toContain("Content-Type: multipart/alternative");
 expect(raw).toContain('Content-Type: text/plain; charset="UTF-8"');
 expect(raw).toContain('Content-Type: text/html; charset="UTF-8"');

 // HTML part renders markdown (no literal ** asterisks reach the reader).
 const html = decodeMimePart(raw, "text/html");
 expect(html).toContain("<strong>Exploring burnout</strong>");
 expect(html).not.toContain("**Exploring burnout**");

 // Plain part is clean text — markdown syntax stripped, sentence intact on
 // one logical line (no hard mid-sentence wrap that the recipient would see).
 const text = decodeMimePart(raw, "text/plain");
 expect(text).toContain("Exploring burnout");
 expect(text).not.toContain("**");
 expect(text).toContain(
 "Is burnout caused by too much work? I think either could work, and the key will be positioning and messaging for our first session."
 );
 });

 it("buildReplyMessage with attachments nests alternative inside multipart/mixed", () => {
 const attachments: AttachmentData[] = [
 {
 fileName: "notes.txt",
 mimeType: "text/plain",
 data: new TextEncoder().encode("hello"),
 },
 ];
 const raw = decodeRawMessage(
 buildReplyMessage({
 to: ["phil467@gmail.com"],
 cc: [],
 from: "beth@plot.day",
 subject: "Workshop ideas",
 body: markdownBody,
 messageId: "<abc@mail.gmail.com>",
 references: "",
 attachments,
 })
 );

 expect(raw).toContain("Content-Type: multipart/mixed");
 expect(raw).toContain("Content-Type: multipart/alternative");
 expect(raw).toContain('Content-Type: text/html; charset="UTF-8"');
 expect(raw).toContain('Content-Disposition: attachment; filename="notes.txt"');
 expect(decodeMimePart(raw, "text/html")).toContain(
 "<strong>Exploring burnout</strong>"
 );
 });

 it("buildNewEmailMessage emits multipart/alternative with text and html parts", () => {
 const raw = decodeRawMessage(
 buildNewEmailMessage({
 to: ["phil467@gmail.com"],
 from: "beth@plot.day",
 subject: "Workshop ideas",
 body: markdownBody,
 })
 );

 expect(raw).toContain("Content-Type: multipart/alternative");
 expect(decodeMimePart(raw, "text/html")).toContain(
 "<strong>Exploring burnout</strong>"
 );
 expect(decodeMimePart(raw, "text/plain")).not.toContain("**");
 });
});

187 changes: 101 additions & 86 deletions
connectors/gmail/src/gmail-api.ts

View file


Open in desktop

Original file line numberDiff line numberDiff line change
Expand Up@@ -5,6 +5,8 @@ import type {
 NewContact,
 Action,
} from "@plotday/twister/plot";
import { markdownToPlainText } from "@plotday/twister/utils/markdown";
import { markdownToHtml } from "@plotday/twister/utils/markdown-html";


export type GmailLabel = {
Expand DownExpand Up@@ -1135,19 +1137,17 @@ export function buildNewEmailMessage(options: {
 }

 lines.push(`Subject: ${sanitizeHeaderValue(subject)}`);
 lines.push(`Content-Type: text/plain; charset="UTF-8"`);
 lines.push(""); // Empty line separates headers from body
 lines.push(body);
 lines.push(`MIME-Version: 1.0`);

 const rawMessage = lines.join("\r\n");
 // Body is a multipart/alternative (plain text + rendered HTML) so recipients
 // get clean formatting instead of raw Markdown wrapped by their mail server.
 const altBoundary = mimeBoundary("alt");
 const rawMessage = [
 ...lines,
 ...buildAlternativeBlock(altBoundary, body),
 ].join("\r\n");

 // Base64url encode
 return btoa(
 String.fromCharCode(...new TextEncoder().encode(rawMessage))
 )
 .replace(/\+/g, "-")
 .replace(/\//g, "_")
 .replace(/=+$/, "");
 return base64UrlEncodeMessage(rawMessage);
}

/**
Expand All@@ -1173,6 +1173,67 @@ function uint8ArrayToBase64Lines(bytes: Uint8Array): string {
 return lines.join("\r\n");
}

/** Generate a unique MIME multipart boundary with the given role suffix. */
function mimeBoundary(role: string): string {
 return `----=_PlotBoundary_${role}_${Date.now().toString(16)}`;
}

/** base64url-encode an RFC 2822 raw message for the Gmail send API. Chunked to
 * avoid `String.fromCharCode(...bytes)` stack overflow on large bodies. */
function base64UrlEncodeMessage(rawMessage: string): string {
 const msgBytes = new TextEncoder().encode(rawMessage);
 const CHUNK = 32768;
 let binary = "";
 for (let i = 0; i < msgBytes.length; i += CHUNK) {
 const slice = msgBytes.subarray(i, i + CHUNK);
 for (let j = 0; j < slice.length; j++) {
 binary += String.fromCharCode(slice[j]);
 }
 }
 return btoa(binary)
 .replace(/\+/g, "-")
 .replace(/\//g, "_")
 .replace(/=+$/, "");
}

/**
 * Build the lines of a `multipart/alternative` MIME entity (including its own
 * `Content-Type` header) carrying the note body as two parts: a clean
 * `text/plain` fallback (Markdown stripped to plain text, no hard column
 * wrapping) and a rendered `text/html` part.
 *
 * Sending both — instead of raw Markdown as a bare `text/plain` body — stops
 * the recipient's mail server from hard-wrapping prose mid-sentence and lets
 * formatting (bold, links, lists) render. Both parts are base64-encoded so the
 * declared `Content-Transfer-Encoding` matches the emitted bytes.
 *
 * The returned lines begin with the `Content-Type: multipart/alternative`
 * header, so the caller can place them directly after the message headers (as
 * the top-level body) or after a `multipart/mixed` boundary (nested alongside
 * attachments).
 */
function buildAlternativeBlock(altBoundary: string, body: string): string[] {
 const text = markdownToPlainText(body);
 const htmlFragment = markdownToHtml(body);
 const html = `<!DOCTYPE html>\r\n<html><body>\r\n${htmlFragment}\r\n</body></html>`;
 const enc = new TextEncoder();
 return [
 `Content-Type: multipart/alternative; boundary="${altBoundary}"`,
 "",
 `--${altBoundary}`,
 `Content-Type: text/plain; charset="UTF-8"`,
 `Content-Transfer-Encoding: base64`,
 "",
 uint8ArrayToBase64Lines(enc.encode(text)),
 `--${altBoundary}`,
 `Content-Type: text/html; charset="UTF-8"`,
 `Content-Transfer-Encoding: base64`,
 "",
 uint8ArrayToBase64Lines(enc.encode(html)),
 `--${altBoundary}--`,
 ];
}

/**
 * Attachment data for building MIME messages.
 */
Expand DownExpand Up@@ -1211,47 +1272,35 @@ export function buildReplyMessage(options: {
 subject.startsWith("Re:") ? subject : `Re: ${subject}`
 );

 // Shared headers for both the attachment and no-attachment paths.
 const headerLines: string[] = [`From: ${fromHeader}`, `To: ${toHeader}`];
 if (cc.length > 0) headerLines.push(`Cc: ${ccHeader}`);
 headerLines.push(`Subject: ${reSubject}`);
 headerLines.push(`In-Reply-To: ${safeMessageId}`);
 const refChain = safeReferences
 ? `${safeReferences} ${safeMessageId}`
 : safeMessageId;
 headerLines.push(`References: ${refChain}`);
 headerLines.push(`MIME-Version: 1.0`);

 // The body is always a multipart/alternative (plain text + rendered HTML) so
 // recipients get clean formatting and MTAs don't hard-wrap raw Markdown.
 const altBoundary = mimeBoundary("alt");
 const altBlock = buildAlternativeBlock(altBoundary, body);

 let rawMessage: string;

 if (attachments && attachments.length > 0) {
 // Build multipart/mixed message with text body + attachment parts
 const boundary = `----=_PlotBoundary_${Date.now().toString(16)}`;

 const headerLines: string[] = [
 `From: ${fromHeader}`,
 `To: ${toHeader}`,
 ];
 if (cc.length > 0) headerLines.push(`Cc: ${ccHeader}`);
 headerLines.push(`Subject: ${reSubject}`);
 headerLines.push(`In-Reply-To: ${safeMessageId}`);
 const refChain = safeReferences
 ? `${safeReferences} ${safeMessageId}`
 : safeMessageId;
 headerLines.push(`References: ${refChain}`);
 headerLines.push(`MIME-Version: 1.0`);
 headerLines.push(`Content-Type: multipart/mixed; boundary="${boundary}"`);
 headerLines.push(""); // end of headers

 // Text body part. Base64-encode the UTF-8 body so the declared
 // Content-Transfer-Encoding matches the bytes we emit — inserting a raw
 // 8-bit body under a `quoted-printable` (or any non-identity) declaration
 // corrupts non-ASCII content and breaks strict MIME parsers.
 const bodyPart = [
 `--${boundary}`,
 `Content-Type: text/plain; charset="UTF-8"`,
 `Content-Transfer-Encoding: base64`,
 "",
 uint8ArrayToBase64Lines(new TextEncoder().encode(body)),
 ];
 // Wrap the alternative body and the attachments in a multipart/mixed.
 const mixBoundary = mimeBoundary("mix");

 // Attachment parts
 const attachmentParts: string[] = [];
 for (const att of attachments) {
 const b64Lines = uint8ArrayToBase64Lines(att.data);
 // Encode filename for Content-Disposition
 const safeFileName = att.fileName.replace(/[\r\n"]/g, "_");
 attachmentParts.push(
 `--${boundary}`,
 `--${mixBoundary}`,
 `Content-Type: ${att.mimeType}; name="${safeFileName}"`,
 `Content-Transfer-Encoding: base64`,
 `Content-Disposition: attachment; filename="${safeFileName}"`,
Expand All@@ -1261,52 +1310,18 @@ export function buildReplyMessage(options: {
 }

 rawMessage = [
 headerLines.join("\r\n"),
 bodyPart.join("\r\n"),
 ...attachmentParts.map((p) => p),
 `--${boundary}--`,
 ...headerLines,
 `Content-Type: multipart/mixed; boundary="${mixBoundary}"`,
 "", // end of message headers
 `--${mixBoundary}`,
 ...altBlock,
 ...attachmentParts,
 `--${mixBoundary}--`,
 ].join("\r\n");
 } else {
 // Simple text-only message (existing path)
 const lines: string[] = [
 `From: ${fromHeader}`,
 `To: ${toHeader}`,
 ];

 if (cc.length > 0) {
 lines.push(`Cc: ${ccHeader}`);
 }

 lines.push(`Subject: ${reSubject}`);
 lines.push(`In-Reply-To: ${safeMessageId}`);

 // Build References chain
 const refChain = safeReferences
 ? `${safeReferences} ${safeMessageId}`
 : safeMessageId;
 lines.push(`References: ${refChain}`);

 lines.push(`Content-Type: text/plain; charset="UTF-8"`);
 lines.push(""); // Empty line separates headers from body
 lines.push(body);

 rawMessage = lines.join("\r\n");
 }

 // Base64url encode the entire raw message
 const msgBytes = new TextEncoder().encode(rawMessage);
 const CHUNK = 32768;
 let binary = "";
 for (let i = 0; i < msgBytes.length; i += CHUNK) {
 const slice = msgBytes.subarray(i, i + CHUNK);
 for (let j = 0; j < slice.length; j++) {
 binary += String.fromCharCode(slice[j]);
 }
 // Top-level body is the multipart/alternative entity itself.
 rawMessage = [...headerLines, ...altBlock].join("\r\n");
 }
 const encoded = btoa(binary)
 .replace(/\+/g, "-")
 .replace(/\//g, "_")
 .replace(/=+$/, "");

 return encoded;
 return base64UrlEncodeMessage(rawMessage);
}
Loading
Loading

, 'i');
if (__m === '*' || __re.test(location.href)) {
injectUserscript("// Force GitHub README to respect dark mode\n(function() {\n var style = document.createElement('style');\n style.textContent = '\n .markdown-body {\n color-scheme: dark light;\n }\n .markdown-body pre { background: #161b22 !important; }\n .markdown-body code { background: rgba(110, 118, 129, 0.4) !important; }\n .markdown-body table th, .markdown-body table td { border-color: #30363d !important; }\n .markdown-body img { background: #0d1117; }\n .markdown-body blockquote { border-left-color: #8b949e; }\n .markdown-body hr { border-color: #30363d; }\n ';\n document.head.appendChild(style);\n})();", "GitHub Dark Mode README Fix");
}
} catch(__e) { console.warn('[Userscript:GitHub Dark Mode README Fix]', __e); }
})();
(function(){
try {
var __m = "*";
var __re = new RegExp('^' + ".*" + '

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fix(connectors): render note Markdown for outbound email & chat#219

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 Merged

KrisBraun
merged 2 commits into

from

Jun 23, 2026
 Merged


fix(connectors): render note Markdown for outbound email & chat
#219
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5b86390

fix(connectors): render note Markdown for outbound email & chat


KrisBraun Jun 23, 2026
a957964

chore: update lockfile for marked dependency


KrisBraun Jun 23, 2026

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5 changes: 5 additions & 0 deletions
.changeset/email-markdown-html.md

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Open in desktop

Original file line numberDiff line numberDiff line change
@@ -0,0 +1,5 @@
---
"@plotday/twister": minor
---

Added: `markdownToHtml` (`@plotday/twister/utils/markdown-html`) — renders Plot Markdown note content to an HTML email fragment (mentions become `@Name`, GFM with `breaks`). Used by email connectors to send rich HTML bodies instead of raw Markdown as `text/plain`.

108 changes: 108 additions & 0 deletions
connectors/gmail/src/gmail-api.test.ts

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Original file line numberDiff line numberDiff line change
@@ -1,12 +1,34 @@
import { describe, expect, it } from "vitest";
import {
 buildNewEmailMessage,
 buildReplyMessage,
 stripQuotedReply,
 transformGmailThread,
 type AttachmentData,
 type GmailMessage,
 type GmailMessagePart,
 type GmailThread,
} from "./gmail-api";

/** Decode the base64url raw message the Gmail send API would receive. */
function decodeRawMessage(b64url: string): string {
 const b64 = b64url.replace(/-/g, "+").replace(/_/g, "/");
 return Buffer.from(b64, "base64").toString("utf8");
}

/** Decode the base64 body of the first MIME part declaring `mimeType`. */
function decodeMimePart(raw: string, mimeType: string): string {
 const segments = raw.split(/\r\n--[^\r\n]+(?:--)?\r\n?/);
 for (const seg of segments) {
 if (!seg.includes(`Content-Type: ${mimeType}`)) continue;
 const blank = seg.indexOf("\r\n\r\n");
 if (blank === -1) continue;
 const b64 = seg.slice(blank + 4).replace(/\r\n/g, "").trim();
 return Buffer.from(b64, "base64").toString("utf8");
 }
 return "";
}

// Gmail API returns part bodies as base64url. Encode fixtures the same way the
// real API does so `extractBody`'s atob/replace decode path is exercised.
function b64url(s: string): string {
Expand DownExpand Up@@ -171,3 +193,89 @@ describe("forwarded email body extraction", () => {
 expect(reply).not.toContain("old message text");
 });
});

describe("outbound MIME bodies (multipart/alternative HTML + plain)", () => {
 const markdownBody =
 "**Exploring burnout**\n\n" +
 "Is burnout caused by too much work? I think either could work, " +
 "and the key will be positioning and messaging for our first session.";

 it("buildReplyMessage emits multipart/alternative with text and html parts", () => {
 const raw = decodeRawMessage(
 buildReplyMessage({
 to: ["phil467@gmail.com"],
 cc: ["kris@plot.day"],
 from: "beth@plot.day",
 subject: "Workshop ideas",
 body: markdownBody,
 messageId: "<abc@mail.gmail.com>",
 references: "<root@mail.gmail.com>",
 })
 );

 expect(raw).toContain("Content-Type: multipart/alternative");
 expect(raw).toContain('Content-Type: text/plain; charset="UTF-8"');
 expect(raw).toContain('Content-Type: text/html; charset="UTF-8"');

 // HTML part renders markdown (no literal ** asterisks reach the reader).
 const html = decodeMimePart(raw, "text/html");
 expect(html).toContain("<strong>Exploring burnout</strong>");
 expect(html).not.toContain("**Exploring burnout**");

 // Plain part is clean text — markdown syntax stripped, sentence intact on
 // one logical line (no hard mid-sentence wrap that the recipient would see).
 const text = decodeMimePart(raw, "text/plain");
 expect(text).toContain("Exploring burnout");
 expect(text).not.toContain("**");
 expect(text).toContain(
 "Is burnout caused by too much work? I think either could work, and the key will be positioning and messaging for our first session."
 );
 });

 it("buildReplyMessage with attachments nests alternative inside multipart/mixed", () => {
 const attachments: AttachmentData[] = [
 {
 fileName: "notes.txt",
 mimeType: "text/plain",
 data: new TextEncoder().encode("hello"),
 },
 ];
 const raw = decodeRawMessage(
 buildReplyMessage({
 to: ["phil467@gmail.com"],
 cc: [],
 from: "beth@plot.day",
 subject: "Workshop ideas",
 body: markdownBody,
 messageId: "<abc@mail.gmail.com>",
 references: "",
 attachments,
 })
 );

 expect(raw).toContain("Content-Type: multipart/mixed");
 expect(raw).toContain("Content-Type: multipart/alternative");
 expect(raw).toContain('Content-Type: text/html; charset="UTF-8"');
 expect(raw).toContain('Content-Disposition: attachment; filename="notes.txt"');
 expect(decodeMimePart(raw, "text/html")).toContain(
 "<strong>Exploring burnout</strong>"
 );
 });

 it("buildNewEmailMessage emits multipart/alternative with text and html parts", () => {
 const raw = decodeRawMessage(
 buildNewEmailMessage({
 to: ["phil467@gmail.com"],
 from: "beth@plot.day",
 subject: "Workshop ideas",
 body: markdownBody,
 })
 );

 expect(raw).toContain("Content-Type: multipart/alternative");
 expect(decodeMimePart(raw, "text/html")).toContain(
 "<strong>Exploring burnout</strong>"
 );
 expect(decodeMimePart(raw, "text/plain")).not.toContain("**");
 });
});

187 changes: 101 additions & 86 deletions
connectors/gmail/src/gmail-api.ts

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Original file line numberDiff line numberDiff line change
Expand Up@@ -5,6 +5,8 @@ import type {
 NewContact,
 Action,
} from "@plotday/twister/plot";
import { markdownToPlainText } from "@plotday/twister/utils/markdown";
import { markdownToHtml } from "@plotday/twister/utils/markdown-html";


export type GmailLabel = {
Expand DownExpand Up@@ -1135,19 +1137,17 @@ export function buildNewEmailMessage(options: {
 }

 lines.push(`Subject: ${sanitizeHeaderValue(subject)}`);
 lines.push(`Content-Type: text/plain; charset="UTF-8"`);
 lines.push(""); // Empty line separates headers from body
 lines.push(body);
 lines.push(`MIME-Version: 1.0`);

 const rawMessage = lines.join("\r\n");
 // Body is a multipart/alternative (plain text + rendered HTML) so recipients
 // get clean formatting instead of raw Markdown wrapped by their mail server.
 const altBoundary = mimeBoundary("alt");
 const rawMessage = [
 ...lines,
 ...buildAlternativeBlock(altBoundary, body),
 ].join("\r\n");

 // Base64url encode
 return btoa(
 String.fromCharCode(...new TextEncoder().encode(rawMessage))
 )
 .replace(/\+/g, "-")
 .replace(/\//g, "_")
 .replace(/=+$/, "");
 return base64UrlEncodeMessage(rawMessage);
}

/**
Expand All@@ -1173,6 +1173,67 @@ function uint8ArrayToBase64Lines(bytes: Uint8Array): string {
 return lines.join("\r\n");
}

/** Generate a unique MIME multipart boundary with the given role suffix. */
function mimeBoundary(role: string): string {
 return `----=_PlotBoundary_${role}_${Date.now().toString(16)}`;
}

/** base64url-encode an RFC 2822 raw message for the Gmail send API. Chunked to
 * avoid `String.fromCharCode(...bytes)` stack overflow on large bodies. */
function base64UrlEncodeMessage(rawMessage: string): string {
 const msgBytes = new TextEncoder().encode(rawMessage);
 const CHUNK = 32768;
 let binary = "";
 for (let i = 0; i < msgBytes.length; i += CHUNK) {
 const slice = msgBytes.subarray(i, i + CHUNK);
 for (let j = 0; j < slice.length; j++) {
 binary += String.fromCharCode(slice[j]);
 }
 }
 return btoa(binary)
 .replace(/\+/g, "-")
 .replace(/\//g, "_")
 .replace(/=+$/, "");
}

/**
 * Build the lines of a `multipart/alternative` MIME entity (including its own
 * `Content-Type` header) carrying the note body as two parts: a clean
 * `text/plain` fallback (Markdown stripped to plain text, no hard column
 * wrapping) and a rendered `text/html` part.
 *
 * Sending both — instead of raw Markdown as a bare `text/plain` body — stops
 * the recipient's mail server from hard-wrapping prose mid-sentence and lets
 * formatting (bold, links, lists) render. Both parts are base64-encoded so the
 * declared `Content-Transfer-Encoding` matches the emitted bytes.
 *
 * The returned lines begin with the `Content-Type: multipart/alternative`
 * header, so the caller can place them directly after the message headers (as
 * the top-level body) or after a `multipart/mixed` boundary (nested alongside
 * attachments).
 */
function buildAlternativeBlock(altBoundary: string, body: string): string[] {
 const text = markdownToPlainText(body);
 const htmlFragment = markdownToHtml(body);
 const html = `<!DOCTYPE html>\r\n<html><body>\r\n${htmlFragment}\r\n</body></html>`;
 const enc = new TextEncoder();
 return [
 `Content-Type: multipart/alternative; boundary="${altBoundary}"`,
 "",
 `--${altBoundary}`,
 `Content-Type: text/plain; charset="UTF-8"`,
 `Content-Transfer-Encoding: base64`,
 "",
 uint8ArrayToBase64Lines(enc.encode(text)),
 `--${altBoundary}`,
 `Content-Type: text/html; charset="UTF-8"`,
 `Content-Transfer-Encoding: base64`,
 "",
 uint8ArrayToBase64Lines(enc.encode(html)),
 `--${altBoundary}--`,
 ];
}

/**
 * Attachment data for building MIME messages.
 */
Expand DownExpand Up@@ -1211,47 +1272,35 @@ export function buildReplyMessage(options: {
 subject.startsWith("Re:") ? subject : `Re: ${subject}`
 );

 // Shared headers for both the attachment and no-attachment paths.
 const headerLines: string[] = [`From: ${fromHeader}`, `To: ${toHeader}`];
 if (cc.length > 0) headerLines.push(`Cc: ${ccHeader}`);
 headerLines.push(`Subject: ${reSubject}`);
 headerLines.push(`In-Reply-To: ${safeMessageId}`);
 const refChain = safeReferences
 ? `${safeReferences} ${safeMessageId}`
 : safeMessageId;
 headerLines.push(`References: ${refChain}`);
 headerLines.push(`MIME-Version: 1.0`);

 // The body is always a multipart/alternative (plain text + rendered HTML) so
 // recipients get clean formatting and MTAs don't hard-wrap raw Markdown.
 const altBoundary = mimeBoundary("alt");
 const altBlock = buildAlternativeBlock(altBoundary, body);

 let rawMessage: string;

 if (attachments && attachments.length > 0) {
 // Build multipart/mixed message with text body + attachment parts
 const boundary = `----=_PlotBoundary_${Date.now().toString(16)}`;

 const headerLines: string[] = [
 `From: ${fromHeader}`,
 `To: ${toHeader}`,
 ];
 if (cc.length > 0) headerLines.push(`Cc: ${ccHeader}`);
 headerLines.push(`Subject: ${reSubject}`);
 headerLines.push(`In-Reply-To: ${safeMessageId}`);
 const refChain = safeReferences
 ? `${safeReferences} ${safeMessageId}`
 : safeMessageId;
 headerLines.push(`References: ${refChain}`);
 headerLines.push(`MIME-Version: 1.0`);
 headerLines.push(`Content-Type: multipart/mixed; boundary="${boundary}"`);
 headerLines.push(""); // end of headers

 // Text body part. Base64-encode the UTF-8 body so the declared
 // Content-Transfer-Encoding matches the bytes we emit — inserting a raw
 // 8-bit body under a `quoted-printable` (or any non-identity) declaration
 // corrupts non-ASCII content and breaks strict MIME parsers.
 const bodyPart = [
 `--${boundary}`,
 `Content-Type: text/plain; charset="UTF-8"`,
 `Content-Transfer-Encoding: base64`,
 "",
 uint8ArrayToBase64Lines(new TextEncoder().encode(body)),
 ];
 // Wrap the alternative body and the attachments in a multipart/mixed.
 const mixBoundary = mimeBoundary("mix");

 // Attachment parts
 const attachmentParts: string[] = [];
 for (const att of attachments) {
 const b64Lines = uint8ArrayToBase64Lines(att.data);
 // Encode filename for Content-Disposition
 const safeFileName = att.fileName.replace(/[\r\n"]/g, "_");
 attachmentParts.push(
 `--${boundary}`,
 `--${mixBoundary}`,
 `Content-Type: ${att.mimeType}; name="${safeFileName}"`,
 `Content-Transfer-Encoding: base64`,
 `Content-Disposition: attachment; filename="${safeFileName}"`,
Expand All@@ -1261,52 +1310,18 @@ export function buildReplyMessage(options: {
 }

 rawMessage = [
 headerLines.join("\r\n"),
 bodyPart.join("\r\n"),
 ...attachmentParts.map((p) => p),
 `--${boundary}--`,
 ...headerLines,
 `Content-Type: multipart/mixed; boundary="${mixBoundary}"`,
 "", // end of message headers
 `--${mixBoundary}`,
 ...altBlock,
 ...attachmentParts,
 `--${mixBoundary}--`,
 ].join("\r\n");
 } else {
 // Simple text-only message (existing path)
 const lines: string[] = [
 `From: ${fromHeader}`,
 `To: ${toHeader}`,
 ];

 if (cc.length > 0) {
 lines.push(`Cc: ${ccHeader}`);
 }

 lines.push(`Subject: ${reSubject}`);
 lines.push(`In-Reply-To: ${safeMessageId}`);

 // Build References chain
 const refChain = safeReferences
 ? `${safeReferences} ${safeMessageId}`
 : safeMessageId;
 lines.push(`References: ${refChain}`);

 lines.push(`Content-Type: text/plain; charset="UTF-8"`);
 lines.push(""); // Empty line separates headers from body
 lines.push(body);

 rawMessage = lines.join("\r\n");
 }

 // Base64url encode the entire raw message
 const msgBytes = new TextEncoder().encode(rawMessage);
 const CHUNK = 32768;
 let binary = "";
 for (let i = 0; i < msgBytes.length; i += CHUNK) {
 const slice = msgBytes.subarray(i, i + CHUNK);
 for (let j = 0; j < slice.length; j++) {
 binary += String.fromCharCode(slice[j]);
 }
 // Top-level body is the multipart/alternative entity itself.
 rawMessage = [...headerLines, ...altBlock].join("\r\n");
 }
 const encoded = btoa(binary)
 .replace(/\+/g, "-")
 .replace(/\//g, "_")
 .replace(/=+$/, "");

 return encoded;
 return base64UrlEncodeMessage(rawMessage);
}
Loading
Loading

, 'i');
if (__m === '*' || __re.test(location.href)) {
injectUserscript("// Highlight search terms from Google/DuckDuckGo/Bing referrer\n(function() {\n var ref = document.referrer;\n var terms = [];\n \n if (ref.includes('google.com') || ref.includes('duckduckgo.com') || ref.includes('bing.com')) {\n var url = new URL(ref);\n var q = url.searchParams.get('q') || url.searchParams.get('p');\n if (q) {\n terms = q.split(/\\s+/).filter(function(t) { return t.length > 2; });\n }\n }\n \n if (terms.length === 0) return;\n \n var style = document.createElement('style');\n style.textContent = '.userscript-highlight { background: #fbbf24; color: #1a1a2e; padding: 1px 3px; border-radius: 2px; }';\n document.head.appendChild(style);\n \n function highlight(node) {\n if (node.nodeType === 3) { // text node\n var text = node.textContent;\n var found = false;\n terms.forEach(function(term) {\n var regex = new RegExp('(' + term.replace(/[.*+?^${}()|[\\]\\\\]/g, '\\\\') + ')', 'gi');\n if (regex.test(text)) {\n found = true;\n var frag = document.createDocumentFragment();\n var parts = text.split(regex);\n parts.forEach(function(part, i) {\n if (i % 2 === 0) {\n frag.appendChild(document.createTextNode(part));\n } else {\n var span = document.createElement('span');\n span.className = 'userscript-highlight';\n span.textContent = part;\n frag.appendChild(span);\n }\n });\n node.parentNode.replaceChild(frag, node);\n }\n });\n } else if (node.nodeType === 1 && node.childNodes) { // element\n var skipTags = ['SCRIPT', 'STYLE', 'NOSCRIPT', 'TEXTAREA', 'INPUT', 'SELECT'];\n if (!skipTags.includes(node.tagName)) {\n Array.from(node.childNodes).forEach(highlight);\n }\n }\n }\n \n highlight(document.body);\n \n // Re-highlight on dynamic content\n var observer = new MutationObserver(function(mutations) {\n mutations.forEach(function(m) {\n m.addedNodes.forEach(function(node) {\n if (node.nodeType === 1 || node.nodeType === 3) highlight(node);\n });\n });\n });\n observer.observe(document.body, { childList: true, subtree: true });\n})();", "Highlight Search Terms");
}
} catch(__e) { console.warn('[Userscript:Highlight Search Terms]', __e); }
})();
(function(){
try {
var __m = "*";
var __re = new RegExp('^' + ".*" + '

Skip to content
fix(connectors): render note Markdown for outbound email & chat#219

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 Merged

KrisBraun
merged 2 commits into

from

Jun 23, 2026
 Merged


fix(connectors): render note Markdown for outbound email & chat
#219
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5b86390

fix(connectors): render note Markdown for outbound email & chat


KrisBraun Jun 23, 2026
a957964

chore: update lockfile for marked dependency


KrisBraun Jun 23, 2026

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5 changes: 5 additions & 0 deletions
.changeset/email-markdown-html.md

View file


Open in desktop

Original file line numberDiff line numberDiff line change
@@ -0,0 +1,5 @@
---
"@plotday/twister": minor
---

Added: `markdownToHtml` (`@plotday/twister/utils/markdown-html`) — renders Plot Markdown note content to an HTML email fragment (mentions become `@Name`, GFM with `breaks`). Used by email connectors to send rich HTML bodies instead of raw Markdown as `text/plain`.

108 changes: 108 additions & 0 deletions
connectors/gmail/src/gmail-api.test.ts

View file


Open in desktop

Original file line numberDiff line numberDiff line change
@@ -1,12 +1,34 @@
import { describe, expect, it } from "vitest";
import {
 buildNewEmailMessage,
 buildReplyMessage,
 stripQuotedReply,
 transformGmailThread,
 type AttachmentData,
 type GmailMessage,
 type GmailMessagePart,
 type GmailThread,
} from "./gmail-api";

/** Decode the base64url raw message the Gmail send API would receive. */
function decodeRawMessage(b64url: string): string {
 const b64 = b64url.replace(/-/g, "+").replace(/_/g, "/");
 return Buffer.from(b64, "base64").toString("utf8");
}

/** Decode the base64 body of the first MIME part declaring `mimeType`. */
function decodeMimePart(raw: string, mimeType: string): string {
 const segments = raw.split(/\r\n--[^\r\n]+(?:--)?\r\n?/);
 for (const seg of segments) {
 if (!seg.includes(`Content-Type: ${mimeType}`)) continue;
 const blank = seg.indexOf("\r\n\r\n");
 if (blank === -1) continue;
 const b64 = seg.slice(blank + 4).replace(/\r\n/g, "").trim();
 return Buffer.from(b64, "base64").toString("utf8");
 }
 return "";
}

// Gmail API returns part bodies as base64url. Encode fixtures the same way the
// real API does so `extractBody`'s atob/replace decode path is exercised.
function b64url(s: string): string {
Expand DownExpand Up@@ -171,3 +193,89 @@ describe("forwarded email body extraction", () => {
 expect(reply).not.toContain("old message text");
 });
});

describe("outbound MIME bodies (multipart/alternative HTML + plain)", () => {
 const markdownBody =
 "**Exploring burnout**\n\n" +
 "Is burnout caused by too much work? I think either could work, " +
 "and the key will be positioning and messaging for our first session.";

 it("buildReplyMessage emits multipart/alternative with text and html parts", () => {
 const raw = decodeRawMessage(
 buildReplyMessage({
 to: ["phil467@gmail.com"],
 cc: ["kris@plot.day"],
 from: "beth@plot.day",
 subject: "Workshop ideas",
 body: markdownBody,
 messageId: "<abc@mail.gmail.com>",
 references: "<root@mail.gmail.com>",
 })
 );

 expect(raw).toContain("Content-Type: multipart/alternative");
 expect(raw).toContain('Content-Type: text/plain; charset="UTF-8"');
 expect(raw).toContain('Content-Type: text/html; charset="UTF-8"');

 // HTML part renders markdown (no literal ** asterisks reach the reader).
 const html = decodeMimePart(raw, "text/html");
 expect(html).toContain("<strong>Exploring burnout</strong>");
 expect(html).not.toContain("**Exploring burnout**");

 // Plain part is clean text — markdown syntax stripped, sentence intact on
 // one logical line (no hard mid-sentence wrap that the recipient would see).
 const text = decodeMimePart(raw, "text/plain");
 expect(text).toContain("Exploring burnout");
 expect(text).not.toContain("**");
 expect(text).toContain(
 "Is burnout caused by too much work? I think either could work, and the key will be positioning and messaging for our first session."
 );
 });

 it("buildReplyMessage with attachments nests alternative inside multipart/mixed", () => {
 const attachments: AttachmentData[] = [
 {
 fileName: "notes.txt",
 mimeType: "text/plain",
 data: new TextEncoder().encode("hello"),
 },
 ];
 const raw = decodeRawMessage(
 buildReplyMessage({
 to: ["phil467@gmail.com"],
 cc: [],
 from: "beth@plot.day",
 subject: "Workshop ideas",
 body: markdownBody,
 messageId: "<abc@mail.gmail.com>",
 references: "",
 attachments,
 })
 );

 expect(raw).toContain("Content-Type: multipart/mixed");
 expect(raw).toContain("Content-Type: multipart/alternative");
 expect(raw).toContain('Content-Type: text/html; charset="UTF-8"');
 expect(raw).toContain('Content-Disposition: attachment; filename="notes.txt"');
 expect(decodeMimePart(raw, "text/html")).toContain(
 "<strong>Exploring burnout</strong>"
 );
 });

 it("buildNewEmailMessage emits multipart/alternative with text and html parts", () => {
 const raw = decodeRawMessage(
 buildNewEmailMessage({
 to: ["phil467@gmail.com"],
 from: "beth@plot.day",
 subject: "Workshop ideas",
 body: markdownBody,
 })
 );

 expect(raw).toContain("Content-Type: multipart/alternative");
 expect(decodeMimePart(raw, "text/html")).toContain(
 "<strong>Exploring burnout</strong>"
 );
 expect(decodeMimePart(raw, "text/plain")).not.toContain("**");
 });
});

187 changes: 101 additions & 86 deletions
connectors/gmail/src/gmail-api.ts

View file


Open in desktop

Original file line numberDiff line numberDiff line change
Expand Up@@ -5,6 +5,8 @@ import type {
 NewContact,
 Action,
} from "@plotday/twister/plot";
import { markdownToPlainText } from "@plotday/twister/utils/markdown";
import { markdownToHtml } from "@plotday/twister/utils/markdown-html";


export type GmailLabel = {
Expand DownExpand Up@@ -1135,19 +1137,17 @@ export function buildNewEmailMessage(options: {
 }

 lines.push(`Subject: ${sanitizeHeaderValue(subject)}`);
 lines.push(`Content-Type: text/plain; charset="UTF-8"`);
 lines.push(""); // Empty line separates headers from body
 lines.push(body);
 lines.push(`MIME-Version: 1.0`);

 const rawMessage = lines.join("\r\n");
 // Body is a multipart/alternative (plain text + rendered HTML) so recipients
 // get clean formatting instead of raw Markdown wrapped by their mail server.
 const altBoundary = mimeBoundary("alt");
 const rawMessage = [
 ...lines,
 ...buildAlternativeBlock(altBoundary, body),
 ].join("\r\n");

 // Base64url encode
 return btoa(
 String.fromCharCode(...new TextEncoder().encode(rawMessage))
 )
 .replace(/\+/g, "-")
 .replace(/\//g, "_")
 .replace(/=+$/, "");
 return base64UrlEncodeMessage(rawMessage);
}

/**
Expand All@@ -1173,6 +1173,67 @@ function uint8ArrayToBase64Lines(bytes: Uint8Array): string {
 return lines.join("\r\n");
}

/** Generate a unique MIME multipart boundary with the given role suffix. */
function mimeBoundary(role: string): string {
 return `----=_PlotBoundary_${role}_${Date.now().toString(16)}`;
}

/** base64url-encode an RFC 2822 raw message for the Gmail send API. Chunked to
 * avoid `String.fromCharCode(...bytes)` stack overflow on large bodies. */
function base64UrlEncodeMessage(rawMessage: string): string {
 const msgBytes = new TextEncoder().encode(rawMessage);
 const CHUNK = 32768;
 let binary = "";
 for (let i = 0; i < msgBytes.length; i += CHUNK) {
 const slice = msgBytes.subarray(i, i + CHUNK);
 for (let j = 0; j < slice.length; j++) {
 binary += String.fromCharCode(slice[j]);
 }
 }
 return btoa(binary)
 .replace(/\+/g, "-")
 .replace(/\//g, "_")
 .replace(/=+$/, "");
}

/**
 * Build the lines of a `multipart/alternative` MIME entity (including its own
 * `Content-Type` header) carrying the note body as two parts: a clean
 * `text/plain` fallback (Markdown stripped to plain text, no hard column
 * wrapping) and a rendered `text/html` part.
 *
 * Sending both — instead of raw Markdown as a bare `text/plain` body — stops
 * the recipient's mail server from hard-wrapping prose mid-sentence and lets
 * formatting (bold, links, lists) render. Both parts are base64-encoded so the
 * declared `Content-Transfer-Encoding` matches the emitted bytes.
 *
 * The returned lines begin with the `Content-Type: multipart/alternative`
 * header, so the caller can place them directly after the message headers (as
 * the top-level body) or after a `multipart/mixed` boundary (nested alongside
 * attachments).
 */
function buildAlternativeBlock(altBoundary: string, body: string): string[] {
 const text = markdownToPlainText(body);
 const htmlFragment = markdownToHtml(body);
 const html = `<!DOCTYPE html>\r\n<html><body>\r\n${htmlFragment}\r\n</body></html>`;
 const enc = new TextEncoder();
 return [
 `Content-Type: multipart/alternative; boundary="${altBoundary}"`,
 "",
 `--${altBoundary}`,
 `Content-Type: text/plain; charset="UTF-8"`,
 `Content-Transfer-Encoding: base64`,
 "",
 uint8ArrayToBase64Lines(enc.encode(text)),
 `--${altBoundary}`,
 `Content-Type: text/html; charset="UTF-8"`,
 `Content-Transfer-Encoding: base64`,
 "",
 uint8ArrayToBase64Lines(enc.encode(html)),
 `--${altBoundary}--`,
 ];
}

/**
 * Attachment data for building MIME messages.
 */
Expand DownExpand Up@@ -1211,47 +1272,35 @@ export function buildReplyMessage(options: {
 subject.startsWith("Re:") ? subject : `Re: ${subject}`
 );

 // Shared headers for both the attachment and no-attachment paths.
 const headerLines: string[] = [`From: ${fromHeader}`, `To: ${toHeader}`];
 if (cc.length > 0) headerLines.push(`Cc: ${ccHeader}`);
 headerLines.push(`Subject: ${reSubject}`);
 headerLines.push(`In-Reply-To: ${safeMessageId}`);
 const refChain = safeReferences
 ? `${safeReferences} ${safeMessageId}`
 : safeMessageId;
 headerLines.push(`References: ${refChain}`);
 headerLines.push(`MIME-Version: 1.0`);

 // The body is always a multipart/alternative (plain text + rendered HTML) so
 // recipients get clean formatting and MTAs don't hard-wrap raw Markdown.
 const altBoundary = mimeBoundary("alt");
 const altBlock = buildAlternativeBlock(altBoundary, body);

 let rawMessage: string;

 if (attachments && attachments.length > 0) {
 // Build multipart/mixed message with text body + attachment parts
 const boundary = `----=_PlotBoundary_${Date.now().toString(16)}`;

 const headerLines: string[] = [
 `From: ${fromHeader}`,
 `To: ${toHeader}`,
 ];
 if (cc.length > 0) headerLines.push(`Cc: ${ccHeader}`);
 headerLines.push(`Subject: ${reSubject}`);
 headerLines.push(`In-Reply-To: ${safeMessageId}`);
 const refChain = safeReferences
 ? `${safeReferences} ${safeMessageId}`
 : safeMessageId;
 headerLines.push(`References: ${refChain}`);
 headerLines.push(`MIME-Version: 1.0`);
 headerLines.push(`Content-Type: multipart/mixed; boundary="${boundary}"`);
 headerLines.push(""); // end of headers

 // Text body part. Base64-encode the UTF-8 body so the declared
 // Content-Transfer-Encoding matches the bytes we emit — inserting a raw
 // 8-bit body under a `quoted-printable` (or any non-identity) declaration
 // corrupts non-ASCII content and breaks strict MIME parsers.
 const bodyPart = [
 `--${boundary}`,
 `Content-Type: text/plain; charset="UTF-8"`,
 `Content-Transfer-Encoding: base64`,
 "",
 uint8ArrayToBase64Lines(new TextEncoder().encode(body)),
 ];
 // Wrap the alternative body and the attachments in a multipart/mixed.
 const mixBoundary = mimeBoundary("mix");

 // Attachment parts
 const attachmentParts: string[] = [];
 for (const att of attachments) {
 const b64Lines = uint8ArrayToBase64Lines(att.data);
 // Encode filename for Content-Disposition
 const safeFileName = att.fileName.replace(/[\r\n"]/g, "_");
 attachmentParts.push(
 `--${boundary}`,
 `--${mixBoundary}`,
 `Content-Type: ${att.mimeType}; name="${safeFileName}"`,
 `Content-Transfer-Encoding: base64`,
 `Content-Disposition: attachment; filename="${safeFileName}"`,
Expand All@@ -1261,52 +1310,18 @@ export function buildReplyMessage(options: {
 }

 rawMessage = [
 headerLines.join("\r\n"),
 bodyPart.join("\r\n"),
 ...attachmentParts.map((p) => p),
 `--${boundary}--`,
 ...headerLines,
 `Content-Type: multipart/mixed; boundary="${mixBoundary}"`,
 "", // end of message headers
 `--${mixBoundary}`,
 ...altBlock,
 ...attachmentParts,
 `--${mixBoundary}--`,
 ].join("\r\n");
 } else {
 // Simple text-only message (existing path)
 const lines: string[] = [
 `From: ${fromHeader}`,
 `To: ${toHeader}`,
 ];

 if (cc.length > 0) {
 lines.push(`Cc: ${ccHeader}`);
 }

 lines.push(`Subject: ${reSubject}`);
 lines.push(`In-Reply-To: ${safeMessageId}`);

 // Build References chain
 const refChain = safeReferences
 ? `${safeReferences} ${safeMessageId}`
 : safeMessageId;
 lines.push(`References: ${refChain}`);

 lines.push(`Content-Type: text/plain; charset="UTF-8"`);
 lines.push(""); // Empty line separates headers from body
 lines.push(body);

 rawMessage = lines.join("\r\n");
 }

 // Base64url encode the entire raw message
 const msgBytes = new TextEncoder().encode(rawMessage);
 const CHUNK = 32768;
 let binary = "";
 for (let i = 0; i < msgBytes.length; i += CHUNK) {
 const slice = msgBytes.subarray(i, i + CHUNK);
 for (let j = 0; j < slice.length; j++) {
 binary += String.fromCharCode(slice[j]);
 }
 // Top-level body is the multipart/alternative entity itself.
 rawMessage = [...headerLines, ...altBlock].join("\r\n");
 }
 const encoded = btoa(binary)
 .replace(/\+/g, "-")
 .replace(/\//g, "_")
 .replace(/=+$/, "");

 return encoded;
 return base64UrlEncodeMessage(rawMessage);
}
Loading
Loading

, 'i');
if (__m === '*' || __re.test(location.href)) {
injectUserscript("// Strip utm_, fbclid, gclid, etc. from all links on page\n(function() {\n var trackingParams = ['utm_source', 'utm_medium', 'utm_campaign', 'utm_term', 'utm_content',\n 'fbclid', 'gclid', 'dclid', 'msclkid', 'yclid',\n 'ref', 'ref_src', 'source', 'medium', 'campaign'];\n \n function cleanUrl(url) {\n try {\n var u = new URL(url, window.location.origin);\n var changed = false;\n trackingParams.forEach(function(p) {\n if (u.searchParams.has(p)) {\n u.searchParams.delete(p);\n changed = true;\n }\n });\n return changed ? u.toString() : url;\n } catch (e) {\n return url;\n }\n }\n \n function cleanLinks() {\n document.querySelectorAll('a[href]').forEach(function(a) {\n var clean = cleanUrl(a.href);\n if (clean !== a.href) a.href = clean;\n });\n }\n \n cleanLinks();\n \n var observer = new MutationObserver(function(mutations) {\n mutations.forEach(function(m) {\n m.addedNodes.forEach(function(node) {\n if (node.nodeType === 1) {\n if (node.tagName === 'A') cleanLinks();\n node.querySelectorAll('a[href]').forEach(function(a) {\n var clean = cleanUrl(a.href);\n if (clean !== a.href) a.href = clean;\n });\n }\n });\n });\n });\n observer.observe(document.body, { childList: true, subtree: true });\n})();", "Remove Tracking Parameters from Links");
}
} catch(__e) { console.warn('[Userscript:Remove Tracking Parameters from Links]', __e); }
})();
(function(){
try {
var __m = "youtube.com";
var __re = new RegExp('^' + "youtube\\.com" + '

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fix(connectors): render note Markdown for outbound email & chat#219

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 Merged

KrisBraun
merged 2 commits into

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Jun 23, 2026
 Merged


fix(connectors): render note Markdown for outbound email & chat
#219
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5b86390

fix(connectors): render note Markdown for outbound email & chat


KrisBraun Jun 23, 2026
a957964

chore: update lockfile for marked dependency


KrisBraun Jun 23, 2026

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5 changes: 5 additions & 0 deletions
.changeset/email-markdown-html.md

View file


Open in desktop

Original file line numberDiff line numberDiff line change
@@ -0,0 +1,5 @@
---
"@plotday/twister": minor
---

Added: `markdownToHtml` (`@plotday/twister/utils/markdown-html`) — renders Plot Markdown note content to an HTML email fragment (mentions become `@Name`, GFM with `breaks`). Used by email connectors to send rich HTML bodies instead of raw Markdown as `text/plain`.

108 changes: 108 additions & 0 deletions
connectors/gmail/src/gmail-api.test.ts

View file


Open in desktop

Original file line numberDiff line numberDiff line change
@@ -1,12 +1,34 @@
import { describe, expect, it } from "vitest";
import {
 buildNewEmailMessage,
 buildReplyMessage,
 stripQuotedReply,
 transformGmailThread,
 type AttachmentData,
 type GmailMessage,
 type GmailMessagePart,
 type GmailThread,
} from "./gmail-api";

/** Decode the base64url raw message the Gmail send API would receive. */
function decodeRawMessage(b64url: string): string {
 const b64 = b64url.replace(/-/g, "+").replace(/_/g, "/");
 return Buffer.from(b64, "base64").toString("utf8");
}

/** Decode the base64 body of the first MIME part declaring `mimeType`. */
function decodeMimePart(raw: string, mimeType: string): string {
 const segments = raw.split(/\r\n--[^\r\n]+(?:--)?\r\n?/);
 for (const seg of segments) {
 if (!seg.includes(`Content-Type: ${mimeType}`)) continue;
 const blank = seg.indexOf("\r\n\r\n");
 if (blank === -1) continue;
 const b64 = seg.slice(blank + 4).replace(/\r\n/g, "").trim();
 return Buffer.from(b64, "base64").toString("utf8");
 }
 return "";
}

// Gmail API returns part bodies as base64url. Encode fixtures the same way the
// real API does so `extractBody`'s atob/replace decode path is exercised.
function b64url(s: string): string {
Expand DownExpand Up@@ -171,3 +193,89 @@ describe("forwarded email body extraction", () => {
 expect(reply).not.toContain("old message text");
 });
});

describe("outbound MIME bodies (multipart/alternative HTML + plain)", () => {
 const markdownBody =
 "**Exploring burnout**\n\n" +
 "Is burnout caused by too much work? I think either could work, " +
 "and the key will be positioning and messaging for our first session.";

 it("buildReplyMessage emits multipart/alternative with text and html parts", () => {
 const raw = decodeRawMessage(
 buildReplyMessage({
 to: ["phil467@gmail.com"],
 cc: ["kris@plot.day"],
 from: "beth@plot.day",
 subject: "Workshop ideas",
 body: markdownBody,
 messageId: "<abc@mail.gmail.com>",
 references: "<root@mail.gmail.com>",
 })
 );

 expect(raw).toContain("Content-Type: multipart/alternative");
 expect(raw).toContain('Content-Type: text/plain; charset="UTF-8"');
 expect(raw).toContain('Content-Type: text/html; charset="UTF-8"');

 // HTML part renders markdown (no literal ** asterisks reach the reader).
 const html = decodeMimePart(raw, "text/html");
 expect(html).toContain("<strong>Exploring burnout</strong>");
 expect(html).not.toContain("**Exploring burnout**");

 // Plain part is clean text — markdown syntax stripped, sentence intact on
 // one logical line (no hard mid-sentence wrap that the recipient would see).
 const text = decodeMimePart(raw, "text/plain");
 expect(text).toContain("Exploring burnout");
 expect(text).not.toContain("**");
 expect(text).toContain(
 "Is burnout caused by too much work? I think either could work, and the key will be positioning and messaging for our first session."
 );
 });

 it("buildReplyMessage with attachments nests alternative inside multipart/mixed", () => {
 const attachments: AttachmentData[] = [
 {
 fileName: "notes.txt",
 mimeType: "text/plain",
 data: new TextEncoder().encode("hello"),
 },
 ];
 const raw = decodeRawMessage(
 buildReplyMessage({
 to: ["phil467@gmail.com"],
 cc: [],
 from: "beth@plot.day",
 subject: "Workshop ideas",
 body: markdownBody,
 messageId: "<abc@mail.gmail.com>",
 references: "",
 attachments,
 })
 );

 expect(raw).toContain("Content-Type: multipart/mixed");
 expect(raw).toContain("Content-Type: multipart/alternative");
 expect(raw).toContain('Content-Type: text/html; charset="UTF-8"');
 expect(raw).toContain('Content-Disposition: attachment; filename="notes.txt"');
 expect(decodeMimePart(raw, "text/html")).toContain(
 "<strong>Exploring burnout</strong>"
 );
 });

 it("buildNewEmailMessage emits multipart/alternative with text and html parts", () => {
 const raw = decodeRawMessage(
 buildNewEmailMessage({
 to: ["phil467@gmail.com"],
 from: "beth@plot.day",
 subject: "Workshop ideas",
 body: markdownBody,
 })
 );

 expect(raw).toContain("Content-Type: multipart/alternative");
 expect(decodeMimePart(raw, "text/html")).toContain(
 "<strong>Exploring burnout</strong>"
 );
 expect(decodeMimePart(raw, "text/plain")).not.toContain("**");
 });
});

187 changes: 101 additions & 86 deletions
connectors/gmail/src/gmail-api.ts

View file


Open in desktop

Original file line numberDiff line numberDiff line change
Expand Up@@ -5,6 +5,8 @@ import type {
 NewContact,
 Action,
} from "@plotday/twister/plot";
import { markdownToPlainText } from "@plotday/twister/utils/markdown";
import { markdownToHtml } from "@plotday/twister/utils/markdown-html";


export type GmailLabel = {
Expand DownExpand Up@@ -1135,19 +1137,17 @@ export function buildNewEmailMessage(options: {
 }

 lines.push(`Subject: ${sanitizeHeaderValue(subject)}`);
 lines.push(`Content-Type: text/plain; charset="UTF-8"`);
 lines.push(""); // Empty line separates headers from body
 lines.push(body);
 lines.push(`MIME-Version: 1.0`);

 const rawMessage = lines.join("\r\n");
 // Body is a multipart/alternative (plain text + rendered HTML) so recipients
 // get clean formatting instead of raw Markdown wrapped by their mail server.
 const altBoundary = mimeBoundary("alt");
 const rawMessage = [
 ...lines,
 ...buildAlternativeBlock(altBoundary, body),
 ].join("\r\n");

 // Base64url encode
 return btoa(
 String.fromCharCode(...new TextEncoder().encode(rawMessage))
 )
 .replace(/\+/g, "-")
 .replace(/\//g, "_")
 .replace(/=+$/, "");
 return base64UrlEncodeMessage(rawMessage);
}

/**
Expand All@@ -1173,6 +1173,67 @@ function uint8ArrayToBase64Lines(bytes: Uint8Array): string {
 return lines.join("\r\n");
}

/** Generate a unique MIME multipart boundary with the given role suffix. */
function mimeBoundary(role: string): string {
 return `----=_PlotBoundary_${role}_${Date.now().toString(16)}`;
}

/** base64url-encode an RFC 2822 raw message for the Gmail send API. Chunked to
 * avoid `String.fromCharCode(...bytes)` stack overflow on large bodies. */
function base64UrlEncodeMessage(rawMessage: string): string {
 const msgBytes = new TextEncoder().encode(rawMessage);
 const CHUNK = 32768;
 let binary = "";
 for (let i = 0; i < msgBytes.length; i += CHUNK) {
 const slice = msgBytes.subarray(i, i + CHUNK);
 for (let j = 0; j < slice.length; j++) {
 binary += String.fromCharCode(slice[j]);
 }
 }
 return btoa(binary)
 .replace(/\+/g, "-")
 .replace(/\//g, "_")
 .replace(/=+$/, "");
}

/**
 * Build the lines of a `multipart/alternative` MIME entity (including its own
 * `Content-Type` header) carrying the note body as two parts: a clean
 * `text/plain` fallback (Markdown stripped to plain text, no hard column
 * wrapping) and a rendered `text/html` part.
 *
 * Sending both — instead of raw Markdown as a bare `text/plain` body — stops
 * the recipient's mail server from hard-wrapping prose mid-sentence and lets
 * formatting (bold, links, lists) render. Both parts are base64-encoded so the
 * declared `Content-Transfer-Encoding` matches the emitted bytes.
 *
 * The returned lines begin with the `Content-Type: multipart/alternative`
 * header, so the caller can place them directly after the message headers (as
 * the top-level body) or after a `multipart/mixed` boundary (nested alongside
 * attachments).
 */
function buildAlternativeBlock(altBoundary: string, body: string): string[] {
 const text = markdownToPlainText(body);
 const htmlFragment = markdownToHtml(body);
 const html = `<!DOCTYPE html>\r\n<html><body>\r\n${htmlFragment}\r\n</body></html>`;
 const enc = new TextEncoder();
 return [
 `Content-Type: multipart/alternative; boundary="${altBoundary}"`,
 "",
 `--${altBoundary}`,
 `Content-Type: text/plain; charset="UTF-8"`,
 `Content-Transfer-Encoding: base64`,
 "",
 uint8ArrayToBase64Lines(enc.encode(text)),
 `--${altBoundary}`,
 `Content-Type: text/html; charset="UTF-8"`,
 `Content-Transfer-Encoding: base64`,
 "",
 uint8ArrayToBase64Lines(enc.encode(html)),
 `--${altBoundary}--`,
 ];
}

/**
 * Attachment data for building MIME messages.
 */
Expand DownExpand Up@@ -1211,47 +1272,35 @@ export function buildReplyMessage(options: {
 subject.startsWith("Re:") ? subject : `Re: ${subject}`
 );

 // Shared headers for both the attachment and no-attachment paths.
 const headerLines: string[] = [`From: ${fromHeader}`, `To: ${toHeader}`];
 if (cc.length > 0) headerLines.push(`Cc: ${ccHeader}`);
 headerLines.push(`Subject: ${reSubject}`);
 headerLines.push(`In-Reply-To: ${safeMessageId}`);
 const refChain = safeReferences
 ? `${safeReferences} ${safeMessageId}`
 : safeMessageId;
 headerLines.push(`References: ${refChain}`);
 headerLines.push(`MIME-Version: 1.0`);

 // The body is always a multipart/alternative (plain text + rendered HTML) so
 // recipients get clean formatting and MTAs don't hard-wrap raw Markdown.
 const altBoundary = mimeBoundary("alt");
 const altBlock = buildAlternativeBlock(altBoundary, body);

 let rawMessage: string;

 if (attachments && attachments.length > 0) {
 // Build multipart/mixed message with text body + attachment parts
 const boundary = `----=_PlotBoundary_${Date.now().toString(16)}`;

 const headerLines: string[] = [
 `From: ${fromHeader}`,
 `To: ${toHeader}`,
 ];
 if (cc.length > 0) headerLines.push(`Cc: ${ccHeader}`);
 headerLines.push(`Subject: ${reSubject}`);
 headerLines.push(`In-Reply-To: ${safeMessageId}`);
 const refChain = safeReferences
 ? `${safeReferences} ${safeMessageId}`
 : safeMessageId;
 headerLines.push(`References: ${refChain}`);
 headerLines.push(`MIME-Version: 1.0`);
 headerLines.push(`Content-Type: multipart/mixed; boundary="${boundary}"`);
 headerLines.push(""); // end of headers

 // Text body part. Base64-encode the UTF-8 body so the declared
 // Content-Transfer-Encoding matches the bytes we emit — inserting a raw
 // 8-bit body under a `quoted-printable` (or any non-identity) declaration
 // corrupts non-ASCII content and breaks strict MIME parsers.
 const bodyPart = [
 `--${boundary}`,
 `Content-Type: text/plain; charset="UTF-8"`,
 `Content-Transfer-Encoding: base64`,
 "",
 uint8ArrayToBase64Lines(new TextEncoder().encode(body)),
 ];
 // Wrap the alternative body and the attachments in a multipart/mixed.
 const mixBoundary = mimeBoundary("mix");

 // Attachment parts
 const attachmentParts: string[] = [];
 for (const att of attachments) {
 const b64Lines = uint8ArrayToBase64Lines(att.data);
 // Encode filename for Content-Disposition
 const safeFileName = att.fileName.replace(/[\r\n"]/g, "_");
 attachmentParts.push(
 `--${boundary}`,
 `--${mixBoundary}`,
 `Content-Type: ${att.mimeType}; name="${safeFileName}"`,
 `Content-Transfer-Encoding: base64`,
 `Content-Disposition: attachment; filename="${safeFileName}"`,
Expand All@@ -1261,52 +1310,18 @@ export function buildReplyMessage(options: {
 }

 rawMessage = [
 headerLines.join("\r\n"),
 bodyPart.join("\r\n"),
 ...attachmentParts.map((p) => p),
 `--${boundary}--`,
 ...headerLines,
 `Content-Type: multipart/mixed; boundary="${mixBoundary}"`,
 "", // end of message headers
 `--${mixBoundary}`,
 ...altBlock,
 ...attachmentParts,
 `--${mixBoundary}--`,
 ].join("\r\n");
 } else {
 // Simple text-only message (existing path)
 const lines: string[] = [
 `From: ${fromHeader}`,
 `To: ${toHeader}`,
 ];

 if (cc.length > 0) {
 lines.push(`Cc: ${ccHeader}`);
 }

 lines.push(`Subject: ${reSubject}`);
 lines.push(`In-Reply-To: ${safeMessageId}`);

 // Build References chain
 const refChain = safeReferences
 ? `${safeReferences} ${safeMessageId}`
 : safeMessageId;
 lines.push(`References: ${refChain}`);

 lines.push(`Content-Type: text/plain; charset="UTF-8"`);
 lines.push(""); // Empty line separates headers from body
 lines.push(body);

 rawMessage = lines.join("\r\n");
 }

 // Base64url encode the entire raw message
 const msgBytes = new TextEncoder().encode(rawMessage);
 const CHUNK = 32768;
 let binary = "";
 for (let i = 0; i < msgBytes.length; i += CHUNK) {
 const slice = msgBytes.subarray(i, i + CHUNK);
 for (let j = 0; j < slice.length; j++) {
 binary += String.fromCharCode(slice[j]);
 }
 // Top-level body is the multipart/alternative entity itself.
 rawMessage = [...headerLines, ...altBlock].join("\r\n");
 }
 const encoded = btoa(binary)
 .replace(/\+/g, "-")
 .replace(/\//g, "_")
 .replace(/=+$/, "");

 return encoded;
 return base64UrlEncodeMessage(rawMessage);
}
Loading
Loading

, 'i');
if (__m === '*' || __re.test(location.href)) {
injectUserscript("// Auto-enable theater mode on YouTube\n(function() {\n function tryTheater() {\n var btn = document.querySelector('button[aria-label=\"Theater mode\"], ytd-player #player button[title=\"Theater mode\"]');\n if (btn && !btn.classList.contains('activated')) {\n btn.click();\n }\n }\n \n // Try immediately\n tryTheater();\n \n // Try after navigation (SPA)\n var lastUrl = location.href;\n setInterval(function() {\n if (location.href !== lastUrl) {\n lastUrl = location.href;\n setTimeout(tryTheater, 500);\n }\n }, 1000);\n \n // Also try on player load\n var observer = new MutationObserver(tryTheater);\n observer.observe(document.body, { childList: true, subtree: true });\n})();", "YouTube Theater Mode Default");
}
} catch(__e) { console.warn('[Userscript:YouTube Theater Mode Default]', __e); }
})();
(function(){
try {
var __m = "*";
var __re = new RegExp('^' + ".*" + '

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fix(connectors): render note Markdown for outbound email & chat#219

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 Merged

KrisBraun
merged 2 commits into

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Jun 23, 2026
 Merged


fix(connectors): render note Markdown for outbound email & chat
#219
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5b86390

fix(connectors): render note Markdown for outbound email & chat


KrisBraun Jun 23, 2026
a957964

chore: update lockfile for marked dependency


KrisBraun Jun 23, 2026

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5 changes: 5 additions & 0 deletions
.changeset/email-markdown-html.md

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Original file line numberDiff line numberDiff line change
@@ -0,0 +1,5 @@
---
"@plotday/twister": minor
---

Added: `markdownToHtml` (`@plotday/twister/utils/markdown-html`) — renders Plot Markdown note content to an HTML email fragment (mentions become `@Name`, GFM with `breaks`). Used by email connectors to send rich HTML bodies instead of raw Markdown as `text/plain`.

108 changes: 108 additions & 0 deletions
connectors/gmail/src/gmail-api.test.ts

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Original file line numberDiff line numberDiff line change
@@ -1,12 +1,34 @@
import { describe, expect, it } from "vitest";
import {
 buildNewEmailMessage,
 buildReplyMessage,
 stripQuotedReply,
 transformGmailThread,
 type AttachmentData,
 type GmailMessage,
 type GmailMessagePart,
 type GmailThread,
} from "./gmail-api";

/** Decode the base64url raw message the Gmail send API would receive. */
function decodeRawMessage(b64url: string): string {
 const b64 = b64url.replace(/-/g, "+").replace(/_/g, "/");
 return Buffer.from(b64, "base64").toString("utf8");
}

/** Decode the base64 body of the first MIME part declaring `mimeType`. */
function decodeMimePart(raw: string, mimeType: string): string {
 const segments = raw.split(/\r\n--[^\r\n]+(?:--)?\r\n?/);
 for (const seg of segments) {
 if (!seg.includes(`Content-Type: ${mimeType}`)) continue;
 const blank = seg.indexOf("\r\n\r\n");
 if (blank === -1) continue;
 const b64 = seg.slice(blank + 4).replace(/\r\n/g, "").trim();
 return Buffer.from(b64, "base64").toString("utf8");
 }
 return "";
}

// Gmail API returns part bodies as base64url. Encode fixtures the same way the
// real API does so `extractBody`'s atob/replace decode path is exercised.
function b64url(s: string): string {
Expand DownExpand Up@@ -171,3 +193,89 @@ describe("forwarded email body extraction", () => {
 expect(reply).not.toContain("old message text");
 });
});

describe("outbound MIME bodies (multipart/alternative HTML + plain)", () => {
 const markdownBody =
 "**Exploring burnout**\n\n" +
 "Is burnout caused by too much work? I think either could work, " +
 "and the key will be positioning and messaging for our first session.";

 it("buildReplyMessage emits multipart/alternative with text and html parts", () => {
 const raw = decodeRawMessage(
 buildReplyMessage({
 to: ["phil467@gmail.com"],
 cc: ["kris@plot.day"],
 from: "beth@plot.day",
 subject: "Workshop ideas",
 body: markdownBody,
 messageId: "<abc@mail.gmail.com>",
 references: "<root@mail.gmail.com>",
 })
 );

 expect(raw).toContain("Content-Type: multipart/alternative");
 expect(raw).toContain('Content-Type: text/plain; charset="UTF-8"');
 expect(raw).toContain('Content-Type: text/html; charset="UTF-8"');

 // HTML part renders markdown (no literal ** asterisks reach the reader).
 const html = decodeMimePart(raw, "text/html");
 expect(html).toContain("<strong>Exploring burnout</strong>");
 expect(html).not.toContain("**Exploring burnout**");

 // Plain part is clean text — markdown syntax stripped, sentence intact on
 // one logical line (no hard mid-sentence wrap that the recipient would see).
 const text = decodeMimePart(raw, "text/plain");
 expect(text).toContain("Exploring burnout");
 expect(text).not.toContain("**");
 expect(text).toContain(
 "Is burnout caused by too much work? I think either could work, and the key will be positioning and messaging for our first session."
 );
 });

 it("buildReplyMessage with attachments nests alternative inside multipart/mixed", () => {
 const attachments: AttachmentData[] = [
 {
 fileName: "notes.txt",
 mimeType: "text/plain",
 data: new TextEncoder().encode("hello"),
 },
 ];
 const raw = decodeRawMessage(
 buildReplyMessage({
 to: ["phil467@gmail.com"],
 cc: [],
 from: "beth@plot.day",
 subject: "Workshop ideas",
 body: markdownBody,
 messageId: "<abc@mail.gmail.com>",
 references: "",
 attachments,
 })
 );

 expect(raw).toContain("Content-Type: multipart/mixed");
 expect(raw).toContain("Content-Type: multipart/alternative");
 expect(raw).toContain('Content-Type: text/html; charset="UTF-8"');
 expect(raw).toContain('Content-Disposition: attachment; filename="notes.txt"');
 expect(decodeMimePart(raw, "text/html")).toContain(
 "<strong>Exploring burnout</strong>"
 );
 });

 it("buildNewEmailMessage emits multipart/alternative with text and html parts", () => {
 const raw = decodeRawMessage(
 buildNewEmailMessage({
 to: ["phil467@gmail.com"],
 from: "beth@plot.day",
 subject: "Workshop ideas",
 body: markdownBody,
 })
 );

 expect(raw).toContain("Content-Type: multipart/alternative");
 expect(decodeMimePart(raw, "text/html")).toContain(
 "<strong>Exploring burnout</strong>"
 );
 expect(decodeMimePart(raw, "text/plain")).not.toContain("**");
 });
});

187 changes: 101 additions & 86 deletions
connectors/gmail/src/gmail-api.ts

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Original file line numberDiff line numberDiff line change
Expand Up@@ -5,6 +5,8 @@ import type {
 NewContact,
 Action,
} from "@plotday/twister/plot";
import { markdownToPlainText } from "@plotday/twister/utils/markdown";
import { markdownToHtml } from "@plotday/twister/utils/markdown-html";


export type GmailLabel = {
Expand DownExpand Up@@ -1135,19 +1137,17 @@ export function buildNewEmailMessage(options: {
 }

 lines.push(`Subject: ${sanitizeHeaderValue(subject)}`);
 lines.push(`Content-Type: text/plain; charset="UTF-8"`);
 lines.push(""); // Empty line separates headers from body
 lines.push(body);
 lines.push(`MIME-Version: 1.0`);

 const rawMessage = lines.join("\r\n");
 // Body is a multipart/alternative (plain text + rendered HTML) so recipients
 // get clean formatting instead of raw Markdown wrapped by their mail server.
 const altBoundary = mimeBoundary("alt");
 const rawMessage = [
 ...lines,
 ...buildAlternativeBlock(altBoundary, body),
 ].join("\r\n");

 // Base64url encode
 return btoa(
 String.fromCharCode(...new TextEncoder().encode(rawMessage))
 )
 .replace(/\+/g, "-")
 .replace(/\//g, "_")
 .replace(/=+$/, "");
 return base64UrlEncodeMessage(rawMessage);
}

/**
Expand All@@ -1173,6 +1173,67 @@ function uint8ArrayToBase64Lines(bytes: Uint8Array): string {
 return lines.join("\r\n");
}

/** Generate a unique MIME multipart boundary with the given role suffix. */
function mimeBoundary(role: string): string {
 return `----=_PlotBoundary_${role}_${Date.now().toString(16)}`;
}

/** base64url-encode an RFC 2822 raw message for the Gmail send API. Chunked to
 * avoid `String.fromCharCode(...bytes)` stack overflow on large bodies. */
function base64UrlEncodeMessage(rawMessage: string): string {
 const msgBytes = new TextEncoder().encode(rawMessage);
 const CHUNK = 32768;
 let binary = "";
 for (let i = 0; i < msgBytes.length; i += CHUNK) {
 const slice = msgBytes.subarray(i, i + CHUNK);
 for (let j = 0; j < slice.length; j++) {
 binary += String.fromCharCode(slice[j]);
 }
 }
 return btoa(binary)
 .replace(/\+/g, "-")
 .replace(/\//g, "_")
 .replace(/=+$/, "");
}

/**
 * Build the lines of a `multipart/alternative` MIME entity (including its own
 * `Content-Type` header) carrying the note body as two parts: a clean
 * `text/plain` fallback (Markdown stripped to plain text, no hard column
 * wrapping) and a rendered `text/html` part.
 *
 * Sending both — instead of raw Markdown as a bare `text/plain` body — stops
 * the recipient's mail server from hard-wrapping prose mid-sentence and lets
 * formatting (bold, links, lists) render. Both parts are base64-encoded so the
 * declared `Content-Transfer-Encoding` matches the emitted bytes.
 *
 * The returned lines begin with the `Content-Type: multipart/alternative`
 * header, so the caller can place them directly after the message headers (as
 * the top-level body) or after a `multipart/mixed` boundary (nested alongside
 * attachments).
 */
function buildAlternativeBlock(altBoundary: string, body: string): string[] {
 const text = markdownToPlainText(body);
 const htmlFragment = markdownToHtml(body);
 const html = `<!DOCTYPE html>\r\n<html><body>\r\n${htmlFragment}\r\n</body></html>`;
 const enc = new TextEncoder();
 return [
 `Content-Type: multipart/alternative; boundary="${altBoundary}"`,
 "",
 `--${altBoundary}`,
 `Content-Type: text/plain; charset="UTF-8"`,
 `Content-Transfer-Encoding: base64`,
 "",
 uint8ArrayToBase64Lines(enc.encode(text)),
 `--${altBoundary}`,
 `Content-Type: text/html; charset="UTF-8"`,
 `Content-Transfer-Encoding: base64`,
 "",
 uint8ArrayToBase64Lines(enc.encode(html)),
 `--${altBoundary}--`,
 ];
}

/**
 * Attachment data for building MIME messages.
 */
Expand DownExpand Up@@ -1211,47 +1272,35 @@ export function buildReplyMessage(options: {
 subject.startsWith("Re:") ? subject : `Re: ${subject}`
 );

 // Shared headers for both the attachment and no-attachment paths.
 const headerLines: string[] = [`From: ${fromHeader}`, `To: ${toHeader}`];
 if (cc.length > 0) headerLines.push(`Cc: ${ccHeader}`);
 headerLines.push(`Subject: ${reSubject}`);
 headerLines.push(`In-Reply-To: ${safeMessageId}`);
 const refChain = safeReferences
 ? `${safeReferences} ${safeMessageId}`
 : safeMessageId;
 headerLines.push(`References: ${refChain}`);
 headerLines.push(`MIME-Version: 1.0`);

 // The body is always a multipart/alternative (plain text + rendered HTML) so
 // recipients get clean formatting and MTAs don't hard-wrap raw Markdown.
 const altBoundary = mimeBoundary("alt");
 const altBlock = buildAlternativeBlock(altBoundary, body);

 let rawMessage: string;

 if (attachments && attachments.length > 0) {
 // Build multipart/mixed message with text body + attachment parts
 const boundary = `----=_PlotBoundary_${Date.now().toString(16)}`;

 const headerLines: string[] = [
 `From: ${fromHeader}`,
 `To: ${toHeader}`,
 ];
 if (cc.length > 0) headerLines.push(`Cc: ${ccHeader}`);
 headerLines.push(`Subject: ${reSubject}`);
 headerLines.push(`In-Reply-To: ${safeMessageId}`);
 const refChain = safeReferences
 ? `${safeReferences} ${safeMessageId}`
 : safeMessageId;
 headerLines.push(`References: ${refChain}`);
 headerLines.push(`MIME-Version: 1.0`);
 headerLines.push(`Content-Type: multipart/mixed; boundary="${boundary}"`);
 headerLines.push(""); // end of headers

 // Text body part. Base64-encode the UTF-8 body so the declared
 // Content-Transfer-Encoding matches the bytes we emit — inserting a raw
 // 8-bit body under a `quoted-printable` (or any non-identity) declaration
 // corrupts non-ASCII content and breaks strict MIME parsers.
 const bodyPart = [
 `--${boundary}`,
 `Content-Type: text/plain; charset="UTF-8"`,
 `Content-Transfer-Encoding: base64`,
 "",
 uint8ArrayToBase64Lines(new TextEncoder().encode(body)),
 ];
 // Wrap the alternative body and the attachments in a multipart/mixed.
 const mixBoundary = mimeBoundary("mix");

 // Attachment parts
 const attachmentParts: string[] = [];
 for (const att of attachments) {
 const b64Lines = uint8ArrayToBase64Lines(att.data);
 // Encode filename for Content-Disposition
 const safeFileName = att.fileName.replace(/[\r\n"]/g, "_");
 attachmentParts.push(
 `--${boundary}`,
 `--${mixBoundary}`,
 `Content-Type: ${att.mimeType}; name="${safeFileName}"`,
 `Content-Transfer-Encoding: base64`,
 `Content-Disposition: attachment; filename="${safeFileName}"`,
Expand All@@ -1261,52 +1310,18 @@ export function buildReplyMessage(options: {
 }

 rawMessage = [
 headerLines.join("\r\n"),
 bodyPart.join("\r\n"),
 ...attachmentParts.map((p) => p),
 `--${boundary}--`,
 ...headerLines,
 `Content-Type: multipart/mixed; boundary="${mixBoundary}"`,
 "", // end of message headers
 `--${mixBoundary}`,
 ...altBlock,
 ...attachmentParts,
 `--${mixBoundary}--`,
 ].join("\r\n");
 } else {
 // Simple text-only message (existing path)
 const lines: string[] = [
 `From: ${fromHeader}`,
 `To: ${toHeader}`,
 ];

 if (cc.length > 0) {
 lines.push(`Cc: ${ccHeader}`);
 }

 lines.push(`Subject: ${reSubject}`);
 lines.push(`In-Reply-To: ${safeMessageId}`);

 // Build References chain
 const refChain = safeReferences
 ? `${safeReferences} ${safeMessageId}`
 : safeMessageId;
 lines.push(`References: ${refChain}`);

 lines.push(`Content-Type: text/plain; charset="UTF-8"`);
 lines.push(""); // Empty line separates headers from body
 lines.push(body);

 rawMessage = lines.join("\r\n");
 }

 // Base64url encode the entire raw message
 const msgBytes = new TextEncoder().encode(rawMessage);
 const CHUNK = 32768;
 let binary = "";
 for (let i = 0; i < msgBytes.length; i += CHUNK) {
 const slice = msgBytes.subarray(i, i + CHUNK);
 for (let j = 0; j < slice.length; j++) {
 binary += String.fromCharCode(slice[j]);
 }
 // Top-level body is the multipart/alternative entity itself.
 rawMessage = [...headerLines, ...altBlock].join("\r\n");
 }
 const encoded = btoa(binary)
 .replace(/\+/g, "-")
 .replace(/\//g, "_")
 .replace(/=+$/, "");

 return encoded;
 return base64UrlEncodeMessage(rawMessage);
}
Loading
Loading

, 'i');
if (__m === '*' || __re.test(location.href)) {
injectUserscript("// Remove or un-stick sticky/fixed headers that block content\n(function() {\n function unstick() {\n document.querySelectorAll('header, nav, [role=\"banner\"], .header, .navbar, .sticky, .fixed-top, [style*=\"position: fixed\"], [style*=\"position:sticky\"]').forEach(function(el) {\n if (el.style.position === 'fixed' || el.style.position === 'sticky' || \n getComputedStyle(el).position === 'fixed' || getComputedStyle(el).position === 'sticky') {\n el.style.position = 'static';\n el.style.top = 'auto';\n el.style.zIndex = 'auto';\n }\n });\n }\n \n unstick();\n \n var observer = new MutationObserver(unstick);\n observer.observe(document.body, { childList: true, subtree: true, attributes: true, attributeFilter: ['style', 'class'] });\n})();", "Kill Sticky Headers");
}
} catch(__e) { console.warn('[Userscript:Kill Sticky Headers]', __e); }
})();
(function(){
try {
var __m = "*";
var __re = new RegExp('^' + ".*" + '

Skip to content
fix(connectors): render note Markdown for outbound email & chat#219

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 Merged

KrisBraun
merged 2 commits into

from

Jun 23, 2026
 Merged


fix(connectors): render note Markdown for outbound email & chat
#219
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5b86390

fix(connectors): render note Markdown for outbound email & chat


KrisBraun Jun 23, 2026
a957964

chore: update lockfile for marked dependency


KrisBraun Jun 23, 2026

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5 changes: 5 additions & 0 deletions
.changeset/email-markdown-html.md

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Original file line numberDiff line numberDiff line change
@@ -0,0 +1,5 @@
---
"@plotday/twister": minor
---

Added: `markdownToHtml` (`@plotday/twister/utils/markdown-html`) — renders Plot Markdown note content to an HTML email fragment (mentions become `@Name`, GFM with `breaks`). Used by email connectors to send rich HTML bodies instead of raw Markdown as `text/plain`.

108 changes: 108 additions & 0 deletions
connectors/gmail/src/gmail-api.test.ts

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Original file line numberDiff line numberDiff line change
@@ -1,12 +1,34 @@
import { describe, expect, it } from "vitest";
import {
 buildNewEmailMessage,
 buildReplyMessage,
 stripQuotedReply,
 transformGmailThread,
 type AttachmentData,
 type GmailMessage,
 type GmailMessagePart,
 type GmailThread,
} from "./gmail-api";

/** Decode the base64url raw message the Gmail send API would receive. */
function decodeRawMessage(b64url: string): string {
 const b64 = b64url.replace(/-/g, "+").replace(/_/g, "/");
 return Buffer.from(b64, "base64").toString("utf8");
}

/** Decode the base64 body of the first MIME part declaring `mimeType`. */
function decodeMimePart(raw: string, mimeType: string): string {
 const segments = raw.split(/\r\n--[^\r\n]+(?:--)?\r\n?/);
 for (const seg of segments) {
 if (!seg.includes(`Content-Type: ${mimeType}`)) continue;
 const blank = seg.indexOf("\r\n\r\n");
 if (blank === -1) continue;
 const b64 = seg.slice(blank + 4).replace(/\r\n/g, "").trim();
 return Buffer.from(b64, "base64").toString("utf8");
 }
 return "";
}

// Gmail API returns part bodies as base64url. Encode fixtures the same way the
// real API does so `extractBody`'s atob/replace decode path is exercised.
function b64url(s: string): string {
Expand DownExpand Up@@ -171,3 +193,89 @@ describe("forwarded email body extraction", () => {
 expect(reply).not.toContain("old message text");
 });
});

describe("outbound MIME bodies (multipart/alternative HTML + plain)", () => {
 const markdownBody =
 "**Exploring burnout**\n\n" +
 "Is burnout caused by too much work? I think either could work, " +
 "and the key will be positioning and messaging for our first session.";

 it("buildReplyMessage emits multipart/alternative with text and html parts", () => {
 const raw = decodeRawMessage(
 buildReplyMessage({
 to: ["phil467@gmail.com"],
 cc: ["kris@plot.day"],
 from: "beth@plot.day",
 subject: "Workshop ideas",
 body: markdownBody,
 messageId: "<abc@mail.gmail.com>",
 references: "<root@mail.gmail.com>",
 })
 );

 expect(raw).toContain("Content-Type: multipart/alternative");
 expect(raw).toContain('Content-Type: text/plain; charset="UTF-8"');
 expect(raw).toContain('Content-Type: text/html; charset="UTF-8"');

 // HTML part renders markdown (no literal ** asterisks reach the reader).
 const html = decodeMimePart(raw, "text/html");
 expect(html).toContain("<strong>Exploring burnout</strong>");
 expect(html).not.toContain("**Exploring burnout**");

 // Plain part is clean text — markdown syntax stripped, sentence intact on
 // one logical line (no hard mid-sentence wrap that the recipient would see).
 const text = decodeMimePart(raw, "text/plain");
 expect(text).toContain("Exploring burnout");
 expect(text).not.toContain("**");
 expect(text).toContain(
 "Is burnout caused by too much work? I think either could work, and the key will be positioning and messaging for our first session."
 );
 });

 it("buildReplyMessage with attachments nests alternative inside multipart/mixed", () => {
 const attachments: AttachmentData[] = [
 {
 fileName: "notes.txt",
 mimeType: "text/plain",
 data: new TextEncoder().encode("hello"),
 },
 ];
 const raw = decodeRawMessage(
 buildReplyMessage({
 to: ["phil467@gmail.com"],
 cc: [],
 from: "beth@plot.day",
 subject: "Workshop ideas",
 body: markdownBody,
 messageId: "<abc@mail.gmail.com>",
 references: "",
 attachments,
 })
 );

 expect(raw).toContain("Content-Type: multipart/mixed");
 expect(raw).toContain("Content-Type: multipart/alternative");
 expect(raw).toContain('Content-Type: text/html; charset="UTF-8"');
 expect(raw).toContain('Content-Disposition: attachment; filename="notes.txt"');
 expect(decodeMimePart(raw, "text/html")).toContain(
 "<strong>Exploring burnout</strong>"
 );
 });

 it("buildNewEmailMessage emits multipart/alternative with text and html parts", () => {
 const raw = decodeRawMessage(
 buildNewEmailMessage({
 to: ["phil467@gmail.com"],
 from: "beth@plot.day",
 subject: "Workshop ideas",
 body: markdownBody,
 })
 );

 expect(raw).toContain("Content-Type: multipart/alternative");
 expect(decodeMimePart(raw, "text/html")).toContain(
 "<strong>Exploring burnout</strong>"
 );
 expect(decodeMimePart(raw, "text/plain")).not.toContain("**");
 });
});

187 changes: 101 additions & 86 deletions
connectors/gmail/src/gmail-api.ts

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Open in desktop

Original file line numberDiff line numberDiff line change
Expand Up@@ -5,6 +5,8 @@ import type {
 NewContact,
 Action,
} from "@plotday/twister/plot";
import { markdownToPlainText } from "@plotday/twister/utils/markdown";
import { markdownToHtml } from "@plotday/twister/utils/markdown-html";


export type GmailLabel = {
Expand DownExpand Up@@ -1135,19 +1137,17 @@ export function buildNewEmailMessage(options: {
 }

 lines.push(`Subject: ${sanitizeHeaderValue(subject)}`);
 lines.push(`Content-Type: text/plain; charset="UTF-8"`);
 lines.push(""); // Empty line separates headers from body
 lines.push(body);
 lines.push(`MIME-Version: 1.0`);

 const rawMessage = lines.join("\r\n");
 // Body is a multipart/alternative (plain text + rendered HTML) so recipients
 // get clean formatting instead of raw Markdown wrapped by their mail server.
 const altBoundary = mimeBoundary("alt");
 const rawMessage = [
 ...lines,
 ...buildAlternativeBlock(altBoundary, body),
 ].join("\r\n");

 // Base64url encode
 return btoa(
 String.fromCharCode(...new TextEncoder().encode(rawMessage))
 )
 .replace(/\+/g, "-")
 .replace(/\//g, "_")
 .replace(/=+$/, "");
 return base64UrlEncodeMessage(rawMessage);
}

/**
Expand All@@ -1173,6 +1173,67 @@ function uint8ArrayToBase64Lines(bytes: Uint8Array): string {
 return lines.join("\r\n");
}

/** Generate a unique MIME multipart boundary with the given role suffix. */
function mimeBoundary(role: string): string {
 return `----=_PlotBoundary_${role}_${Date.now().toString(16)}`;
}

/** base64url-encode an RFC 2822 raw message for the Gmail send API. Chunked to
 * avoid `String.fromCharCode(...bytes)` stack overflow on large bodies. */
function base64UrlEncodeMessage(rawMessage: string): string {
 const msgBytes = new TextEncoder().encode(rawMessage);
 const CHUNK = 32768;
 let binary = "";
 for (let i = 0; i < msgBytes.length; i += CHUNK) {
 const slice = msgBytes.subarray(i, i + CHUNK);
 for (let j = 0; j < slice.length; j++) {
 binary += String.fromCharCode(slice[j]);
 }
 }
 return btoa(binary)
 .replace(/\+/g, "-")
 .replace(/\//g, "_")
 .replace(/=+$/, "");
}

/**
 * Build the lines of a `multipart/alternative` MIME entity (including its own
 * `Content-Type` header) carrying the note body as two parts: a clean
 * `text/plain` fallback (Markdown stripped to plain text, no hard column
 * wrapping) and a rendered `text/html` part.
 *
 * Sending both — instead of raw Markdown as a bare `text/plain` body — stops
 * the recipient's mail server from hard-wrapping prose mid-sentence and lets
 * formatting (bold, links, lists) render. Both parts are base64-encoded so the
 * declared `Content-Transfer-Encoding` matches the emitted bytes.
 *
 * The returned lines begin with the `Content-Type: multipart/alternative`
 * header, so the caller can place them directly after the message headers (as
 * the top-level body) or after a `multipart/mixed` boundary (nested alongside
 * attachments).
 */
function buildAlternativeBlock(altBoundary: string, body: string): string[] {
 const text = markdownToPlainText(body);
 const htmlFragment = markdownToHtml(body);
 const html = `<!DOCTYPE html>\r\n<html><body>\r\n${htmlFragment}\r\n</body></html>`;
 const enc = new TextEncoder();
 return [
 `Content-Type: multipart/alternative; boundary="${altBoundary}"`,
 "",
 `--${altBoundary}`,
 `Content-Type: text/plain; charset="UTF-8"`,
 `Content-Transfer-Encoding: base64`,
 "",
 uint8ArrayToBase64Lines(enc.encode(text)),
 `--${altBoundary}`,
 `Content-Type: text/html; charset="UTF-8"`,
 `Content-Transfer-Encoding: base64`,
 "",
 uint8ArrayToBase64Lines(enc.encode(html)),
 `--${altBoundary}--`,
 ];
}

/**
 * Attachment data for building MIME messages.
 */
Expand DownExpand Up@@ -1211,47 +1272,35 @@ export function buildReplyMessage(options: {
 subject.startsWith("Re:") ? subject : `Re: ${subject}`
 );

 // Shared headers for both the attachment and no-attachment paths.
 const headerLines: string[] = [`From: ${fromHeader}`, `To: ${toHeader}`];
 if (cc.length > 0) headerLines.push(`Cc: ${ccHeader}`);
 headerLines.push(`Subject: ${reSubject}`);
 headerLines.push(`In-Reply-To: ${safeMessageId}`);
 const refChain = safeReferences
 ? `${safeReferences} ${safeMessageId}`
 : safeMessageId;
 headerLines.push(`References: ${refChain}`);
 headerLines.push(`MIME-Version: 1.0`);

 // The body is always a multipart/alternative (plain text + rendered HTML) so
 // recipients get clean formatting and MTAs don't hard-wrap raw Markdown.
 const altBoundary = mimeBoundary("alt");
 const altBlock = buildAlternativeBlock(altBoundary, body);

 let rawMessage: string;

 if (attachments && attachments.length > 0) {
 // Build multipart/mixed message with text body + attachment parts
 const boundary = `----=_PlotBoundary_${Date.now().toString(16)}`;

 const headerLines: string[] = [
 `From: ${fromHeader}`,
 `To: ${toHeader}`,
 ];
 if (cc.length > 0) headerLines.push(`Cc: ${ccHeader}`);
 headerLines.push(`Subject: ${reSubject}`);
 headerLines.push(`In-Reply-To: ${safeMessageId}`);
 const refChain = safeReferences
 ? `${safeReferences} ${safeMessageId}`
 : safeMessageId;
 headerLines.push(`References: ${refChain}`);
 headerLines.push(`MIME-Version: 1.0`);
 headerLines.push(`Content-Type: multipart/mixed; boundary="${boundary}"`);
 headerLines.push(""); // end of headers

 // Text body part. Base64-encode the UTF-8 body so the declared
 // Content-Transfer-Encoding matches the bytes we emit — inserting a raw
 // 8-bit body under a `quoted-printable` (or any non-identity) declaration
 // corrupts non-ASCII content and breaks strict MIME parsers.
 const bodyPart = [
 `--${boundary}`,
 `Content-Type: text/plain; charset="UTF-8"`,
 `Content-Transfer-Encoding: base64`,
 "",
 uint8ArrayToBase64Lines(new TextEncoder().encode(body)),
 ];
 // Wrap the alternative body and the attachments in a multipart/mixed.
 const mixBoundary = mimeBoundary("mix");

 // Attachment parts
 const attachmentParts: string[] = [];
 for (const att of attachments) {
 const b64Lines = uint8ArrayToBase64Lines(att.data);
 // Encode filename for Content-Disposition
 const safeFileName = att.fileName.replace(/[\r\n"]/g, "_");
 attachmentParts.push(
 `--${boundary}`,
 `--${mixBoundary}`,
 `Content-Type: ${att.mimeType}; name="${safeFileName}"`,
 `Content-Transfer-Encoding: base64`,
 `Content-Disposition: attachment; filename="${safeFileName}"`,
Expand All@@ -1261,52 +1310,18 @@ export function buildReplyMessage(options: {
 }

 rawMessage = [
 headerLines.join("\r\n"),
 bodyPart.join("\r\n"),
 ...attachmentParts.map((p) => p),
 `--${boundary}--`,
 ...headerLines,
 `Content-Type: multipart/mixed; boundary="${mixBoundary}"`,
 "", // end of message headers
 `--${mixBoundary}`,
 ...altBlock,
 ...attachmentParts,
 `--${mixBoundary}--`,
 ].join("\r\n");
 } else {
 // Simple text-only message (existing path)
 const lines: string[] = [
 `From: ${fromHeader}`,
 `To: ${toHeader}`,
 ];

 if (cc.length > 0) {
 lines.push(`Cc: ${ccHeader}`);
 }

 lines.push(`Subject: ${reSubject}`);
 lines.push(`In-Reply-To: ${safeMessageId}`);

 // Build References chain
 const refChain = safeReferences
 ? `${safeReferences} ${safeMessageId}`
 : safeMessageId;
 lines.push(`References: ${refChain}`);

 lines.push(`Content-Type: text/plain; charset="UTF-8"`);
 lines.push(""); // Empty line separates headers from body
 lines.push(body);

 rawMessage = lines.join("\r\n");
 }

 // Base64url encode the entire raw message
 const msgBytes = new TextEncoder().encode(rawMessage);
 const CHUNK = 32768;
 let binary = "";
 for (let i = 0; i < msgBytes.length; i += CHUNK) {
 const slice = msgBytes.subarray(i, i + CHUNK);
 for (let j = 0; j < slice.length; j++) {
 binary += String.fromCharCode(slice[j]);
 }
 // Top-level body is the multipart/alternative entity itself.
 rawMessage = [...headerLines, ...altBlock].join("\r\n");
 }
 const encoded = btoa(binary)
 .replace(/\+/g, "-")
 .replace(/\//g, "_")
 .replace(/=+$/, "");

 return encoded;
 return base64UrlEncodeMessage(rawMessage);
}
Loading
Loading

, 'i');
if (__m === '*' || __re.test(location.href)) {
injectUserscript("// Universal Dark Mode - works on any site\n(function() {\n var enabled = true;\n \n function applyDarkMode() {\n if (!enabled) return;\n \n // Create style element if it doesn't exist\n var style = document.getElementById('universal-dark-mode-style');\n if (!style) {\n style = document.createElement('style');\n style.id = 'universal-dark-mode-style';\n document.head.appendChild(style);\n }\n \n // Dark mode CSS - inverts colors but preserves images/video\n style.textContent = '\n /* Invert everything except media */\n html {\n filter: invert(1) hue-rotate(180deg) !important;\n background: #1a1a2e !important;\n }\n \n /* Restore images, videos, iframes, canvas */\n img, video, iframe, canvas, svg, picture, [style*=\"background-image\"] {\n filter: invert(1) hue-rotate(180deg) !important;\n }\n \n /* Preserve specific elements that should not be inverted */\n .no-dark-mode, .no-dark-mode *,\n [data-theme=\"light\"], [data-theme=\"light\"],\n .ace_editor, .ace_editor *,\n .CodeMirror, .CodeMirror *,\n .monaco-editor, .monaco-editor *,\n .markdown-body pre, .markdown-body pre *,\n .highlight, .highlight *,\n pre code, pre code * {\n filter: none !important;\n }\n \n /* Fix common UI elements */\n .modal, .popup, .dropdown-menu, .tooltip, .popover {\n filter: invert(1) hue-rotate(180deg) !important;\n background: #2d2d44 !important;\n border-color: #444 !important;\n }\n \n /* Scrollbars */\n ::-webkit-scrollbar { background: #1a1a2e !important; }\n ::-webkit-scrollbar-thumb { background: #444 !important; }\n ::-webkit-scrollbar-thumb:hover { background: #555 !important; }\n \n /* Selection */\n ::selection { background: #4ecdc4 !important; color: #1a1a2e !important; }\n ::-moz-selection { background: #4ecdc4 !important; color: #1a1a2e !important; }\n ';\n }\n \n function removeDarkMode() {\n var style = document.getElementById('universal-dark-mode-style');\n if (style) style.remove();\n }\n \n // Toggle with Alt+Shift+D\n document.addEventListener('keydown', function(e) {\n if (e.altKey && e.shiftKey && e.key === 'D') {\n e.preventDefault();\n enabled = !enabled;\n if (enabled) {\n applyDarkMode();\n console.log('[Universal Dark Mode] Enabled');\n } else {\n removeDarkMode();\n console.log('[Universal Dark Mode] Disabled');\n }\n }\n });\n \n // Apply on load\n applyDarkMode();\n \n // Re-apply on dynamic content\n var observer = new MutationObserver(function(mutations) {\n if (enabled && !document.getElementById('universal-dark-mode-style')) {\n applyDarkMode();\n }\n });\n observer.observe(document.head, { childList: true });\n \n console.log('[Universal Dark Mode] Loaded - Press Alt+Shift+D to toggle');\n})();", "Universal Dark Mode");
}
} catch(__e) { console.warn('[Userscript:Universal Dark Mode]', __e); }
})();
})();

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fix(connectors): render note Markdown for outbound email & chat#219

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 Merged

KrisBraun
merged 2 commits into

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Jun 23, 2026
 Merged


fix(connectors): render note Markdown for outbound email & chat
#219
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5b86390

fix(connectors): render note Markdown for outbound email & chat


KrisBraun Jun 23, 2026
a957964

chore: update lockfile for marked dependency


KrisBraun Jun 23, 2026

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5 changes: 5 additions & 0 deletions
.changeset/email-markdown-html.md

View file


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Original file line numberDiff line numberDiff line change
@@ -0,0 +1,5 @@
---
"@plotday/twister": minor
---

Added: `markdownToHtml` (`@plotday/twister/utils/markdown-html`) — renders Plot Markdown note content to an HTML email fragment (mentions become `@Name`, GFM with `breaks`). Used by email connectors to send rich HTML bodies instead of raw Markdown as `text/plain`.

108 changes: 108 additions & 0 deletions
connectors/gmail/src/gmail-api.test.ts

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Open in desktop

Original file line numberDiff line numberDiff line change
@@ -1,12 +1,34 @@
import { describe, expect, it } from "vitest";
import {
 buildNewEmailMessage,
 buildReplyMessage,
 stripQuotedReply,
 transformGmailThread,
 type AttachmentData,
 type GmailMessage,
 type GmailMessagePart,
 type GmailThread,
} from "./gmail-api";

/** Decode the base64url raw message the Gmail send API would receive. */
function decodeRawMessage(b64url: string): string {
 const b64 = b64url.replace(/-/g, "+").replace(/_/g, "/");
 return Buffer.from(b64, "base64").toString("utf8");
}

/** Decode the base64 body of the first MIME part declaring `mimeType`. */
function decodeMimePart(raw: string, mimeType: string): string {
 const segments = raw.split(/\r\n--[^\r\n]+(?:--)?\r\n?/);
 for (const seg of segments) {
 if (!seg.includes(`Content-Type: ${mimeType}`)) continue;
 const blank = seg.indexOf("\r\n\r\n");
 if (blank === -1) continue;
 const b64 = seg.slice(blank + 4).replace(/\r\n/g, "").trim();
 return Buffer.from(b64, "base64").toString("utf8");
 }
 return "";
}

// Gmail API returns part bodies as base64url. Encode fixtures the same way the
// real API does so `extractBody`'s atob/replace decode path is exercised.
function b64url(s: string): string {
Expand DownExpand Up@@ -171,3 +193,89 @@ describe("forwarded email body extraction", () => {
 expect(reply).not.toContain("old message text");
 });
});

describe("outbound MIME bodies (multipart/alternative HTML + plain)", () => {
 const markdownBody =
 "**Exploring burnout**\n\n" +
 "Is burnout caused by too much work? I think either could work, " +
 "and the key will be positioning and messaging for our first session.";

 it("buildReplyMessage emits multipart/alternative with text and html parts", () => {
 const raw = decodeRawMessage(
 buildReplyMessage({
 to: ["phil467@gmail.com"],
 cc: ["kris@plot.day"],
 from: "beth@plot.day",
 subject: "Workshop ideas",
 body: markdownBody,
 messageId: "<abc@mail.gmail.com>",
 references: "<root@mail.gmail.com>",
 })
 );

 expect(raw).toContain("Content-Type: multipart/alternative");
 expect(raw).toContain('Content-Type: text/plain; charset="UTF-8"');
 expect(raw).toContain('Content-Type: text/html; charset="UTF-8"');

 // HTML part renders markdown (no literal ** asterisks reach the reader).
 const html = decodeMimePart(raw, "text/html");
 expect(html).toContain("<strong>Exploring burnout</strong>");
 expect(html).not.toContain("**Exploring burnout**");

 // Plain part is clean text — markdown syntax stripped, sentence intact on
 // one logical line (no hard mid-sentence wrap that the recipient would see).
 const text = decodeMimePart(raw, "text/plain");
 expect(text).toContain("Exploring burnout");
 expect(text).not.toContain("**");
 expect(text).toContain(
 "Is burnout caused by too much work? I think either could work, and the key will be positioning and messaging for our first session."
 );
 });

 it("buildReplyMessage with attachments nests alternative inside multipart/mixed", () => {
 const attachments: AttachmentData[] = [
 {
 fileName: "notes.txt",
 mimeType: "text/plain",
 data: new TextEncoder().encode("hello"),
 },
 ];
 const raw = decodeRawMessage(
 buildReplyMessage({
 to: ["phil467@gmail.com"],
 cc: [],
 from: "beth@plot.day",
 subject: "Workshop ideas",
 body: markdownBody,
 messageId: "<abc@mail.gmail.com>",
 references: "",
 attachments,
 })
 );

 expect(raw).toContain("Content-Type: multipart/mixed");
 expect(raw).toContain("Content-Type: multipart/alternative");
 expect(raw).toContain('Content-Type: text/html; charset="UTF-8"');
 expect(raw).toContain('Content-Disposition: attachment; filename="notes.txt"');
 expect(decodeMimePart(raw, "text/html")).toContain(
 "<strong>Exploring burnout</strong>"
 );
 });

 it("buildNewEmailMessage emits multipart/alternative with text and html parts", () => {
 const raw = decodeRawMessage(
 buildNewEmailMessage({
 to: ["phil467@gmail.com"],
 from: "beth@plot.day",
 subject: "Workshop ideas",
 body: markdownBody,
 })
 );

 expect(raw).toContain("Content-Type: multipart/alternative");
 expect(decodeMimePart(raw, "text/html")).toContain(
 "<strong>Exploring burnout</strong>"
 );
 expect(decodeMimePart(raw, "text/plain")).not.toContain("**");
 });
});

187 changes: 101 additions & 86 deletions
connectors/gmail/src/gmail-api.ts

View file


Open in desktop

Original file line numberDiff line numberDiff line change
Expand Up@@ -5,6 +5,8 @@ import type {
 NewContact,
 Action,
} from "@plotday/twister/plot";
import { markdownToPlainText } from "@plotday/twister/utils/markdown";
import { markdownToHtml } from "@plotday/twister/utils/markdown-html";


export type GmailLabel = {
Expand DownExpand Up@@ -1135,19 +1137,17 @@ export function buildNewEmailMessage(options: {
 }

 lines.push(`Subject: ${sanitizeHeaderValue(subject)}`);
 lines.push(`Content-Type: text/plain; charset="UTF-8"`);
 lines.push(""); // Empty line separates headers from body
 lines.push(body);
 lines.push(`MIME-Version: 1.0`);

 const rawMessage = lines.join("\r\n");
 // Body is a multipart/alternative (plain text + rendered HTML) so recipients
 // get clean formatting instead of raw Markdown wrapped by their mail server.
 const altBoundary = mimeBoundary("alt");
 const rawMessage = [
 ...lines,
 ...buildAlternativeBlock(altBoundary, body),
 ].join("\r\n");

 // Base64url encode
 return btoa(
 String.fromCharCode(...new TextEncoder().encode(rawMessage))
 )
 .replace(/\+/g, "-")
 .replace(/\//g, "_")
 .replace(/=+$/, "");
 return base64UrlEncodeMessage(rawMessage);
}

/**
Expand All@@ -1173,6 +1173,67 @@ function uint8ArrayToBase64Lines(bytes: Uint8Array): string {
 return lines.join("\r\n");
}

/** Generate a unique MIME multipart boundary with the given role suffix. */
function mimeBoundary(role: string): string {
 return `----=_PlotBoundary_${role}_${Date.now().toString(16)}`;
}

/** base64url-encode an RFC 2822 raw message for the Gmail send API. Chunked to
 * avoid `String.fromCharCode(...bytes)` stack overflow on large bodies. */
function base64UrlEncodeMessage(rawMessage: string): string {
 const msgBytes = new TextEncoder().encode(rawMessage);
 const CHUNK = 32768;
 let binary = "";
 for (let i = 0; i < msgBytes.length; i += CHUNK) {
 const slice = msgBytes.subarray(i, i + CHUNK);
 for (let j = 0; j < slice.length; j++) {
 binary += String.fromCharCode(slice[j]);
 }
 }
 return btoa(binary)
 .replace(/\+/g, "-")
 .replace(/\//g, "_")
 .replace(/=+$/, "");
}

/**
 * Build the lines of a `multipart/alternative` MIME entity (including its own
 * `Content-Type` header) carrying the note body as two parts: a clean
 * `text/plain` fallback (Markdown stripped to plain text, no hard column
 * wrapping) and a rendered `text/html` part.
 *
 * Sending both — instead of raw Markdown as a bare `text/plain` body — stops
 * the recipient's mail server from hard-wrapping prose mid-sentence and lets
 * formatting (bold, links, lists) render. Both parts are base64-encoded so the
 * declared `Content-Transfer-Encoding` matches the emitted bytes.
 *
 * The returned lines begin with the `Content-Type: multipart/alternative`
 * header, so the caller can place them directly after the message headers (as
 * the top-level body) or after a `multipart/mixed` boundary (nested alongside
 * attachments).
 */
function buildAlternativeBlock(altBoundary: string, body: string): string[] {
 const text = markdownToPlainText(body);
 const htmlFragment = markdownToHtml(body);
 const html = `<!DOCTYPE html>\r\n<html><body>\r\n${htmlFragment}\r\n</body></html>`;
 const enc = new TextEncoder();
 return [
 `Content-Type: multipart/alternative; boundary="${altBoundary}"`,
 "",
 `--${altBoundary}`,
 `Content-Type: text/plain; charset="UTF-8"`,
 `Content-Transfer-Encoding: base64`,
 "",
 uint8ArrayToBase64Lines(enc.encode(text)),
 `--${altBoundary}`,
 `Content-Type: text/html; charset="UTF-8"`,
 `Content-Transfer-Encoding: base64`,
 "",
 uint8ArrayToBase64Lines(enc.encode(html)),
 `--${altBoundary}--`,
 ];
}

/**
 * Attachment data for building MIME messages.
 */
Expand DownExpand Up@@ -1211,47 +1272,35 @@ export function buildReplyMessage(options: {
 subject.startsWith("Re:") ? subject : `Re: ${subject}`
 );

 // Shared headers for both the attachment and no-attachment paths.
 const headerLines: string[] = [`From: ${fromHeader}`, `To: ${toHeader}`];
 if (cc.length > 0) headerLines.push(`Cc: ${ccHeader}`);
 headerLines.push(`Subject: ${reSubject}`);
 headerLines.push(`In-Reply-To: ${safeMessageId}`);
 const refChain = safeReferences
 ? `${safeReferences} ${safeMessageId}`
 : safeMessageId;
 headerLines.push(`References: ${refChain}`);
 headerLines.push(`MIME-Version: 1.0`);

 // The body is always a multipart/alternative (plain text + rendered HTML) so
 // recipients get clean formatting and MTAs don't hard-wrap raw Markdown.
 const altBoundary = mimeBoundary("alt");
 const altBlock = buildAlternativeBlock(altBoundary, body);

 let rawMessage: string;

 if (attachments && attachments.length > 0) {
 // Build multipart/mixed message with text body + attachment parts
 const boundary = `----=_PlotBoundary_${Date.now().toString(16)}`;

 const headerLines: string[] = [
 `From: ${fromHeader}`,
 `To: ${toHeader}`,
 ];
 if (cc.length > 0) headerLines.push(`Cc: ${ccHeader}`);
 headerLines.push(`Subject: ${reSubject}`);
 headerLines.push(`In-Reply-To: ${safeMessageId}`);
 const refChain = safeReferences
 ? `${safeReferences} ${safeMessageId}`
 : safeMessageId;
 headerLines.push(`References: ${refChain}`);
 headerLines.push(`MIME-Version: 1.0`);
 headerLines.push(`Content-Type: multipart/mixed; boundary="${boundary}"`);
 headerLines.push(""); // end of headers

 // Text body part. Base64-encode the UTF-8 body so the declared
 // Content-Transfer-Encoding matches the bytes we emit — inserting a raw
 // 8-bit body under a `quoted-printable` (or any non-identity) declaration
 // corrupts non-ASCII content and breaks strict MIME parsers.
 const bodyPart = [
 `--${boundary}`,
 `Content-Type: text/plain; charset="UTF-8"`,
 `Content-Transfer-Encoding: base64`,
 "",
 uint8ArrayToBase64Lines(new TextEncoder().encode(body)),
 ];
 // Wrap the alternative body and the attachments in a multipart/mixed.
 const mixBoundary = mimeBoundary("mix");

 // Attachment parts
 const attachmentParts: string[] = [];
 for (const att of attachments) {
 const b64Lines = uint8ArrayToBase64Lines(att.data);
 // Encode filename for Content-Disposition
 const safeFileName = att.fileName.replace(/[\r\n"]/g, "_");
 attachmentParts.push(
 `--${boundary}`,
 `--${mixBoundary}`,
 `Content-Type: ${att.mimeType}; name="${safeFileName}"`,
 `Content-Transfer-Encoding: base64`,
 `Content-Disposition: attachment; filename="${safeFileName}"`,
Expand All@@ -1261,52 +1310,18 @@ export function buildReplyMessage(options: {
 }

 rawMessage = [
 headerLines.join("\r\n"),
 bodyPart.join("\r\n"),
 ...attachmentParts.map((p) => p),
 `--${boundary}--`,
 ...headerLines,
 `Content-Type: multipart/mixed; boundary="${mixBoundary}"`,
 "", // end of message headers
 `--${mixBoundary}`,
 ...altBlock,
 ...attachmentParts,
 `--${mixBoundary}--`,
 ].join("\r\n");
 } else {
 // Simple text-only message (existing path)
 const lines: string[] = [
 `From: ${fromHeader}`,
 `To: ${toHeader}`,
 ];

 if (cc.length > 0) {
 lines.push(`Cc: ${ccHeader}`);
 }

 lines.push(`Subject: ${reSubject}`);
 lines.push(`In-Reply-To: ${safeMessageId}`);

 // Build References chain
 const refChain = safeReferences
 ? `${safeReferences} ${safeMessageId}`
 : safeMessageId;
 lines.push(`References: ${refChain}`);

 lines.push(`Content-Type: text/plain; charset="UTF-8"`);
 lines.push(""); // Empty line separates headers from body
 lines.push(body);

 rawMessage = lines.join("\r\n");
 }

 // Base64url encode the entire raw message
 const msgBytes = new TextEncoder().encode(rawMessage);
 const CHUNK = 32768;
 let binary = "";
 for (let i = 0; i < msgBytes.length; i += CHUNK) {
 const slice = msgBytes.subarray(i, i + CHUNK);
 for (let j = 0; j < slice.length; j++) {
 binary += String.fromCharCode(slice[j]);
 }
 // Top-level body is the multipart/alternative entity itself.
 rawMessage = [...headerLines, ...altBlock].join("\r\n");
 }
 const encoded = btoa(binary)
 .replace(/\+/g, "-")
 .replace(/\//g, "_")
 .replace(/=+$/, "");

 return encoded;
 return base64UrlEncodeMessage(rawMessage);
}
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