From cf887ff3a2644203e1276a27a8ce3f38d6f661d0 Mon Sep 17 00:00:00 2001
From: AndresL230 <190146319+AndresL230@users.noreply.github.com>
Date: Fri, 3 Jul 2026 15:02:56 -0400
Subject: [PATCH 1/9] docs(spec): My Work reorder + structured cards +
 retroactive summary resync design

---
 .../2026-07-03-mywork-restructure-design.md   | 140 ++++++++++++++++++
 1 file changed, 140 insertions(+)
 create mode 100644 docs/superpowers/specs/2026-07-03-mywork-restructure-design.md

diff --git a/docs/superpowers/specs/2026-07-03-mywork-restructure-design.md b/docs/superpowers/specs/2026-07-03-mywork-restructure-design.md
new file mode 100644
index 0000000..39ba878
--- /dev/null
+++ b/docs/superpowers/specs/2026-07-03-mywork-restructure-design.md
@@ -0,0 +1,140 @@
+# My Work: reorder, structured cards, retroactive summary resync
+
+Date: 2026-07-03
+
+## Problem
+
+The My Work screen (`web/src/render.ts`, `myWorkView`) shows two sections: "Previous
+activity" (merged/closed PRs) above "To-do" (open assigned issues). Two things are off:
+
+1. To-do — the actionable list — renders below the read-only activity history. It
+   should be on top.
+2. Both sections are thin on structure. `todoCard` is a single truncated line with no
+   room for a full title or an updated-at signal. `prActivityCard`'s body is one
+   undifferentiated AI-generated prose blob — no labeled fields.
+
+Separately, "Sync GitHub" (the admin-only backfill button) only looks at PRs closed in
+the last 14 days, and only (re)generates a PR's summary when its event is *newly*
+captured — an already-captured PR's summary is never touched again. That means
+existing PRs would stay on the old unstructured prose format forever, even after this
+change ships.
+
+## Design
+
+### 1. Reorder (`web/src/render.ts`, `myWorkView`)
+
+Swap section composition from `${hero}${activity}${todo}` to `${hero}${todo}${activity}`.
+Section labels ("To-do", "Previous activity") stay as-is.
+
+### 2. To-do card restructure (`todoCard`)
+
+From a single-line truncated row to a two-line card, still one `<a class="cnpy-card">`:
+
+- Row 1: priority badge + `#number` + title. Title wraps up to 2 lines (CSS
+  line-clamp) instead of single-line ellipsis truncation.
+- Row 2: up to 3 labels (cap unchanged, keeps the card bounded) + a right-aligned
+  relative "updated" timestamp from `t.updatedAt` (captured today, currently unused
+  in the card).
+
+### 3. Structured PR summaries
+
+**New shared module `shared/prSummary.ts`** — the single source of truth for
+recognizing the structured-summary convention, imported by both the Worker and the
+web build:
+
+```ts
+export interface StructuredPrSummary {
+  what: string;
+  why: string | null;
+}
+
+export function parseStructuredSummary(raw: string): StructuredPrSummary | null;
+```
+
+It matches markdown of the shape:
+
+```
+**What changed:** <1-2 factual sentences>
+**Why:** <1 sentence — omitted entirely when no rationale is stated>
+```
+
+Returns `null` when the text doesn't match (old-style prose, the deterministic
+excerpt fallback, or a malformed AI response) — callers treat `null` as "render/treat
+as plain prose," never as an error.
+
+**Backend (`src/tools/summarize.ts`)** — `workersAiSummarizer`'s system prompt
+changes to require exactly that two-field shape (omitting the `**Why:**` line when
+the PR body states no rationale), instead of "2-3 short sentences." No signature
+change. `excerptSummary` (the deterministic no-AI fallback) is untouched — it keeps
+producing plain prose, which is intentional: a parse miss just falls back to today's
+rendering, never a broken UI. `pr_summaries.summary` stays a single `TEXT` column; no
+migration — the structure lives in the markdown convention, not the schema.
+
+**Frontend (`web/src/render.ts`, `prActivityCard`)** — the summary body now branches
+on `parseStructuredSummary(pr.summary)`:
+- Matched → two labeled rows ("What changed", and "Why" only when present), each a
+  small uppercase caption (scaled-down `MW_LABEL` idiom) above its markdown body.
+- Not matched → today's single prose block, unchanged.
+
+### 4. Retroactive resync (`src/tools/backfill.ts`, `runBackfill`)
+
+Two independent changes to `runBackfill`:
+
+**a. Full PR history.** Remove the `DAYS_BACK`/cutoff logic on the closed-PR fetch —
+paginate through every closed PR the repo has, not just the last 14 days. The open-
+issues fetch is untouched (it already has no window).
+
+**b. Decouple summary (re)generation from event-capture outcome.** Today,
+`storePrSummary` only runs inside `if (res.outcome === "written")` — i.e., only for
+brand-new events. Change: for every PR in the fetched list (regardless of whether its
+event was newly captured or already existed), look up its existing `pr_summaries` row
+and call `storePrSummary` unless `parseStructuredSummary(existing.summary) !== null`
+(i.e., skip only when it's already in the new structured format). `ev.raw` (built
+before `ingestEvent` runs) always has the PR's title/body available regardless of the
+event's write outcome, so no extra DB read is needed to get the summarizer input —
+only one extra read (existing `pr_summaries` row) to decide skip-or-regenerate.
+
+**c. Observability.** `BackfillResult` gains `summarized: number` — incremented each
+time `storePrSummary` actually runs (not skipped). Threaded through:
+- `src/routes.ts` `/admin/backfill` response (already returns the whole result object,
+  no route change beyond the type flowing through).
+- `web/src/api.ts` `adminBackfill()` return type.
+- `web/src/main.ts`'s flash message: `Synced: ${r.captured} captured, ${r.unchanged}
+  unchanged, ${r.summarized} summaries updated`.
+- `web/src/render.ts`'s button title: "Fetch recent GitHub PRs + issues" →
+  "Fetch all GitHub PRs + issues" (no longer just recent).
+
+**Accepted limitation:** unbounded full-history pagination plus one AI call per
+un-migrated PR has no hard cap or resumable cursor. Fine at this project's current
+size (a first Sync after this ships does a one-time migration of every existing PR to
+the structured format; later clicks are cheap since already-structured PRs are
+skipped). Would need a real bound/cursor if the repo's PR history grows a lot —
+explicitly not building that now (YAGNI).
+
+## Testing
+
+- `test/render.mywork.test.ts` (pure, no DOM): `todoCard` shows `updatedAt` and
+  doesn't collapse a long title to one truncated line; `prActivityCard` renders two
+  labeled rows for a structured summary (with and without a `why`), and falls back to
+  the existing prose rendering for a non-conforming summary.
+- New test file (or colocated in `test/summarize.test.ts`) for
+  `shared/prSummary.ts`'s `parseStructuredSummary`: matches the two-field shape,
+  matches "What changed" only (no "Why" line), returns `null` for old-style prose and
+  for empty/malformed input.
+- `test/backfill.test.ts`: the existing "oldPr excluded by the 14-day window"
+  assertion is now wrong on purpose and must be updated to reflect full-history
+  fetch. New cases: a PR with an existing non-structured summary gets re-summarized
+  on a second run (`summarized` increments, `storePrSummary`/summarizer called
+  again); a PR with an existing structured summary is skipped on a second run
+  (`summarized` stays 0 for it, summarizer not called again — assert via a
+  call-counting stub summarizer).
+- No new migration, so `test/apply-migrations.ts` is untouched.
+
+## Out of scope
+
+- No change to the live webhook capture path (`src/webhook.ts`) — a real-time merge
+  event only ever fires once, so the "already captured, skip" question doesn't arise
+  there.
+- No change to issue capture/backfill scope (already unbounded).
+- No resumable/bounded backfill cursor for large repos (see accepted limitation
+  above).

From c79120d8a23c1832e5c40ac26aaf4aa3c7638218 Mon Sep 17 00:00:00 2001
From: AndresL230 <190146319+AndresL230@users.noreply.github.com>
Date: Fri, 3 Jul 2026 15:39:47 -0400
Subject: [PATCH 2/9] =?UTF-8?q?feat(shared):=20parseStructuredSummary=20?=
 =?UTF-8?q?=E2=80=94=20What=20changed/Why=20markdown=20convention?=
MIME-Version: 1.0
Content-Type: text/plain; charset=UTF-8
Content-Transfer-Encoding: 8bit

---
 shared/prSummary.ts    | 28 +++++++++++++++++++++++++
 test/prSummary.test.ts | 46 ++++++++++++++++++++++++++++++++++++++++++
 2 files changed, 74 insertions(+)
 create mode 100644 shared/prSummary.ts
 create mode 100644 test/prSummary.test.ts

diff --git a/shared/prSummary.ts b/shared/prSummary.ts
new file mode 100644
index 0000000..bcb90d5
--- /dev/null
+++ b/shared/prSummary.ts
@@ -0,0 +1,28 @@
+// Recognizes the "What changed / Why" markdown convention emitted by the PR
+// summarizer (src/tools/summarize.ts) so both the Worker (the backfill's
+// already-structured check, src/tools/backfill.ts) and the web build (card
+// rendering, web/src/render.ts) agree on what counts as a structured summary.
+// No schema change backs this — pr_summaries.summary stays a single markdown
+// TEXT column; the structure lives in this convention, not a stored shape, so
+// old prose summaries and the deterministic excerpt fallback degrade
+// gracefully to a `null` parse instead of erroring.
+
+export interface StructuredPrSummary {
+  what: string;
+  why: string | null;
+}
+
+const STRUCTURED_RE = /^\s*\*\*What changed:\*\*\s*([\s\S]*?)(?:\s*\*\*Why:\*\*\s*([\s\S]*))?$/i;
+
+/** Parses "**What changed:** ... **Why:** ..." out of a PR summary's markdown.
+ *  Returns null when the text doesn't match (old-style prose, the excerpt
+ *  fallback, or a malformed AI response) — callers treat null as "render/treat
+ *  as plain prose," never as an error. */
+export function parseStructuredSummary(raw: string): StructuredPrSummary | null {
+  const m = raw.match(STRUCTURED_RE);
+  if (!m) return null;
+  const what = m[1].trim();
+  if (!what) return null;
+  const why = m[2]?.trim() || null;
+  return { what, why };
+}
diff --git a/test/prSummary.test.ts b/test/prSummary.test.ts
new file mode 100644
index 0000000..05176a6
--- /dev/null
+++ b/test/prSummary.test.ts
@@ -0,0 +1,46 @@
+import { describe, it, expect } from "vitest";
+import { parseStructuredSummary } from "@shared/prSummary";
+
+describe("parseStructuredSummary", () => {
+  it("parses What changed + Why into separate fields", () => {
+    const raw = "**What changed:** Fixed the login bug.\n**Why:** Users were being logged out unexpectedly.";
+    expect(parseStructuredSummary(raw)).toEqual({
+      what: "Fixed the login bug.",
+      why: "Users were being logged out unexpectedly.",
+    });
+  });
+
+  it("parses What changed alone, why:null, when there is no Why line", () => {
+    const raw = "**What changed:** Fixed the login bug.";
+    expect(parseStructuredSummary(raw)).toEqual({ what: "Fixed the login bug.", why: null });
+  });
+
+  it("handles What changed and Why on the same line", () => {
+    const raw = "**What changed:** Fixed the login bug. **Why:** Users were affected.";
+    expect(parseStructuredSummary(raw)).toEqual({
+      what: "Fixed the login bug.",
+      why: "Users were affected.",
+    });
+  });
+
+  it("is case-insensitive on the labels", () => {
+    const raw = "**what changed:** Fixed the login bug.\n**why:** Users were affected.";
+    expect(parseStructuredSummary(raw)).toEqual({
+      what: "Fixed the login bug.",
+      why: "Users were affected.",
+    });
+  });
+
+  it("returns null for old-style prose with no convention", () => {
+    expect(parseStructuredSummary("Fixed a bug that was breaking the login flow.")).toBeNull();
+  });
+
+  it("returns null for empty input", () => {
+    expect(parseStructuredSummary("")).toBeNull();
+  });
+
+  it("returns null when the What field is empty even if a Why is present", () => {
+    const raw = "**What changed:** \n**Why:** something";
+    expect(parseStructuredSummary(raw)).toBeNull();
+  });
+});

From af5f344953cd4f1efd6e2033c87be523b8370175 Mon Sep 17 00:00:00 2001
From: AndresL230 <190146319+AndresL230@users.noreply.github.com>
Date: Fri, 3 Jul 2026 15:43:17 -0400
Subject: [PATCH 3/9] feat(summarize): require the What changed/Why structured
 markdown convention

---
 src/tools/summarize.ts | 17 ++++++++++++-----
 test/summarize.test.ts |  9 ++++++++-
 2 files changed, 20 insertions(+), 6 deletions(-)

diff --git a/src/tools/summarize.ts b/src/tools/summarize.ts
index 8cf5fdc..3c64caf 100644
--- a/src/tools/summarize.ts
+++ b/src/tools/summarize.ts
@@ -15,6 +15,17 @@ export interface Summarizer {
 
 const WORKERS_AI_MODEL = "@cf/meta/llama-3.1-8b-instruct";
 
+// Exported for a content assertion in test/summarize.test.ts — the two-field
+// shape here is exactly what shared/prSummary.ts's parseStructuredSummary
+// recognizes; keep them in sync if either changes.
+export const SUMMARIZER_SYSTEM_PROMPT =
+  "Summarize this one pull request's description for a team activity feed. " +
+  "Respond with ONLY this exact markdown structure, nothing else:\n" +
+  "**What changed:** <1-2 short factual sentences>\n" +
+  "**Why:** <1 short sentence stating the description's own stated rationale>\n" +
+  'If the description states no rationale, omit the "**Why:**" line entirely. ' +
+  "Do not speculate beyond the text.";
+
 /** Workers AI-backed summarizer. Bounded to THAT PR's own title+body — no other
  *  context is sent. Never throws: any failure (network, empty output, malformed
  *  response) resolves to null so the caller falls back to excerptSummary. */
@@ -25,11 +36,7 @@ export function workersAiSummarizer(ai: Ai): Summarizer {
       try {
         const result = await ai.run(WORKERS_AI_MODEL, {
           messages: [
-            {
-              role: "system",
-              content:
-                "Summarize this one pull request's description in 2-3 short markdown sentences for a team activity feed. Do not speculate beyond the text.",
-            },
+            { role: "system", content: SUMMARIZER_SYSTEM_PROMPT },
             { role: "user", content: `Title: ${title}\n\nBody: ${body}` },
           ],
         });
diff --git a/test/summarize.test.ts b/test/summarize.test.ts
index 9cfe386..95aed54 100644
--- a/test/summarize.test.ts
+++ b/test/summarize.test.ts
@@ -4,7 +4,7 @@ import { all, run, nowIso } from "../src/db";
 import type { PrSummaryRow } from "@shared/rows";
 import type { Env } from "../src/env";
 import type { Summarizer } from "../src/tools/summarize";
-import { storePrSummary, excerptSummary } from "../src/tools/summarize";
+import { storePrSummary, excerptSummary, SUMMARIZER_SYSTEM_PROMPT } from "../src/tools/summarize";
 import { handleGithubWebhook } from "../src/webhook";
 import prMerged from "./fixtures/gh-pr-merged.json";
 import issueAssigned from "./fixtures/gh-issue-assigned.json";
@@ -191,3 +191,10 @@ describe("webhook → summarize wiring", () => {
     expect(rows[0].model).toBe("excerpt");
   });
 });
+
+describe("SUMMARIZER_SYSTEM_PROMPT", () => {
+  it("requires the structured What changed / Why convention", () => {
+    expect(SUMMARIZER_SYSTEM_PROMPT).toContain("**What changed:**");
+    expect(SUMMARIZER_SYSTEM_PROMPT).toContain("**Why:**");
+  });
+});

From de744f9cba67e8f522f22f7c301896cab8385ddb Mon Sep 17 00:00:00 2001
From: AndresL230 <190146319+AndresL230@users.noreply.github.com>
Date: Fri, 3 Jul 2026 15:47:51 -0400
Subject: [PATCH 4/9] feat(mywork): render structured What changed/Why PR
 summaries as labeled rows

---
 test/render.mywork.test.ts | 23 +++++++++++++++++++++++
 web/src/render.ts          | 30 ++++++++++++++++++++++++++----
 2 files changed, 49 insertions(+), 4 deletions(-)

diff --git a/test/render.mywork.test.ts b/test/render.mywork.test.ts
index 59b2cec..8eab342 100644
--- a/test/render.mywork.test.ts
+++ b/test/render.mywork.test.ts
@@ -89,6 +89,29 @@ describe("prActivityCard", () => {
     expect(html).toContain('href="#"');
     expect(html).not.toContain("javascript:alert(1)");
   });
+
+  it("renders structured What changed + Why as separate labeled rows", () => {
+    const pr = makePr({ summary: "**What changed:** Fixed the login bug.\n**Why:** Users were logged out unexpectedly." });
+    const html = prActivityCard(pr, mockMd);
+    expect(html).toContain("What changed");
+    expect(html).toContain("Why");
+    expect(html).toContain("Fixed the login bug.");
+    expect(html).toContain("Users were logged out unexpectedly.");
+  });
+
+  it("omits the Why row when the structured summary has no Why", () => {
+    const pr = makePr({ summary: "**What changed:** Fixed the login bug." });
+    const html = prActivityCard(pr, mockMd);
+    expect(html).toContain("What changed");
+    expect(html).not.toContain("Why");
+  });
+
+  it("falls back to the raw prose block for a non-conforming summary (legacy/excerpt)", () => {
+    const pr = makePr({ summary: "Fixed the login bug that was affecting users." });
+    const html = prActivityCard(pr, mockMd);
+    expect(html).not.toContain("What changed");
+    expect(html).toContain("mock-md");
+  });
 });
 
 // ── todoCard ──────────────────────────────────────────────────────────────────
diff --git a/web/src/render.ts b/web/src/render.ts
index f87e6d4..5f3b818 100644
--- a/web/src/render.ts
+++ b/web/src/render.ts
@@ -8,6 +8,7 @@ import type { FeedRow, DocRow, DocVersionRow } from "@shared/rows";
 import type { QueryResult, QueryPrimary, QueryPointer, Authority, MilestoneWithProgress, PlanView, StagedProposal } from "./api";
 import type { AdrRow, NeedsTriageRow, MilestoneProposalRow } from "@shared/rows";
 import type { DashboardData, MyWorkPr, MyWorkTodo } from "@shared/dashboard";
+import { parseStructuredSummary, type StructuredPrSummary } from "@shared/prSummary";
 import { TAGS } from "@shared/vocabulary";
 import { renderMarkdown } from "./markdown";
 import { REPO_URL } from "./github";
@@ -1329,6 +1330,7 @@ function settingsView(s: AppState): string {
 
 // ── my work (personal dashboard) ──────────────────────────────────────────────
 const MW_LABEL = "font-size:11px;font-weight:600;font-family:var(--mono);text-transform:uppercase;letter-spacing:.1em;color:var(--fg-40)";
+const MW_FIELD_LABEL = "font-size:10px;font-weight:600;font-family:var(--mono);text-transform:uppercase;letter-spacing:.08em;color:var(--fg-40);margin-bottom:3px";
 
 function wrapMyWork(inner: string): string {
   return `<div class="cnpy-scroll" style="max-width:820px;margin:0 auto;padding:32px 32px 100px">${inner}</div>`;
@@ -1351,14 +1353,34 @@ function mwDegradedHint(text: string): string {
   return `<div style="font-size:13px;color:var(--fg-40);padding:2px 0">${text}</div>`;
 }
 
-/** A merged/closed PR card: #number → pr.url, title, relTime, MERGED/CLOSED chip, markdown summary. */
+/** Renders a structured {what, why} summary as labeled rows (small caption + markdown body each). */
+function structuredSummaryBody(structured: StructuredPrSummary, markdownFn: (body: string) => string): string {
+  const whatRow = `<div${structured.why ? ' style="margin-bottom:10px"' : ""}>
+      <div style="${MW_FIELD_LABEL}">What changed</div>
+      <div class="cnpy-md" style="font-size:13.5px;color:var(--fg-70)">${markdownFn(structured.what)}</div>
+    </div>`;
+  const whyRow = structured.why
+    ? `<div>
+      <div style="${MW_FIELD_LABEL}">Why</div>
+      <div class="cnpy-md" style="font-size:13.5px;color:var(--fg-70)">${markdownFn(structured.why)}</div>
+    </div>`
+    : "";
+  return whatRow + whyRow;
+}
+
+/** A merged/closed PR card: #number → pr.url, title, relTime, MERGED/CLOSED chip,
+ *  and a summary body — labeled "What changed"/"Why" rows when pr.summary matches
+ *  the structured convention, else the raw markdown blob (legacy/excerpt fallback). */
 export function prActivityCard(pr: MyWorkPr, markdownFn: (body: string) => string): string {
   const chip = pr.merged
     ? `<span style="font-size:9.5px;font-weight:600;font-family:var(--mono);letter-spacing:.03em;color:var(--green);border:1px solid color-mix(in srgb,var(--green) 45%,transparent);background:color-mix(in srgb,var(--green) 12%,transparent);border-radius:5px;padding:2px 6px;white-space:nowrap">MERGED</span>`
     : `<span style="font-size:9.5px;font-weight:600;font-family:var(--mono);letter-spacing:.03em;color:var(--fg-40);border:1px solid var(--border);border-radius:5px;padding:2px 6px;white-space:nowrap">CLOSED</span>`;
-  const body = pr.summary !== null
-    ? `<div class="cnpy-md" style="font-size:13.5px;color:var(--fg-70)">${markdownFn(pr.summary)}</div>`
-    : `<div style="font-size:13.5px;color:var(--fg-55);line-height:1.6">${linkifyRefs("No summary recorded for this PR.")}</div>`;
+  const structured = pr.summary !== null ? parseStructuredSummary(pr.summary) : null;
+  const body = pr.summary === null
+    ? `<div style="font-size:13.5px;color:var(--fg-55);line-height:1.6">${linkifyRefs("No summary recorded for this PR.")}</div>`
+    : structured !== null
+      ? structuredSummaryBody(structured, markdownFn)
+      : `<div class="cnpy-md" style="font-size:13.5px;color:var(--fg-70)">${markdownFn(pr.summary)}</div>`;
   return `<div class="cnpy-card" style="border:1px solid var(--border);border-radius:13px;padding:14px 16px;margin-bottom:10px">
     <div style="display:flex;align-items:center;justify-content:space-between;gap:10px;margin-bottom:8px">
       <div style="display:flex;align-items:center;gap:9px;min-width:0">

From cb20694d0b470d1e84e064b33d719d124847ce2f Mon Sep 17 00:00:00 2001
From: AndresL230 <190146319+AndresL230@users.noreply.github.com>
Date: Fri, 3 Jul 2026 15:53:22 -0400
Subject: [PATCH 5/9] test(mywork): strengthen prActivityCard
 structured-summary tests to detect a reverted feature

---
 test/render.mywork.test.ts | 3 +++
 1 file changed, 3 insertions(+)

diff --git a/test/render.mywork.test.ts b/test/render.mywork.test.ts
index 8eab342..43dbe78 100644
--- a/test/render.mywork.test.ts
+++ b/test/render.mywork.test.ts
@@ -97,6 +97,8 @@ describe("prActivityCard", () => {
     expect(html).toContain("Why");
     expect(html).toContain("Fixed the login bug.");
     expect(html).toContain("Users were logged out unexpectedly.");
+    expect(html).not.toContain("**What changed:**");
+    expect(html).not.toContain("**Why:**");
   });
 
   it("omits the Why row when the structured summary has no Why", () => {
@@ -104,6 +106,7 @@ describe("prActivityCard", () => {
     const html = prActivityCard(pr, mockMd);
     expect(html).toContain("What changed");
     expect(html).not.toContain("Why");
+    expect(html).not.toContain("**What changed:**");
   });
 
   it("falls back to the raw prose block for a non-conforming summary (legacy/excerpt)", () => {

From 55b11db2efa30ac26480f6369e01105753a78f06 Mon Sep 17 00:00:00 2001
From: AndresL230 <190146319+AndresL230@users.noreply.github.com>
Date: Fri, 3 Jul 2026 15:57:37 -0400
Subject: [PATCH 6/9] feat(mywork): reorder To-do above Previous activity;
 richer To-do cards

---
 test/render.mywork.test.ts | 23 +++++++++++++++++++++++
 web/src/render.ts          | 20 +++++++++++++-------
 2 files changed, 36 insertions(+), 7 deletions(-)

diff --git a/test/render.mywork.test.ts b/test/render.mywork.test.ts
index 43dbe78..231fe24 100644
--- a/test/render.mywork.test.ts
+++ b/test/render.mywork.test.ts
@@ -161,6 +161,18 @@ describe("todoCard", () => {
     expect(html).not.toContain("P2");
     expect(html).not.toContain("P3");
   });
+
+  it("shows a relative 'updated' time derived from t.updatedAt", () => {
+    const threeDaysAgo = new Date(Date.now() - 3 * 24 * 60 * 60 * 1000).toISOString();
+    const html = todoCard(makeTodo({ updatedAt: threeDaysAgo }));
+    expect(html).toContain("3d ago");
+  });
+
+  it("wraps a long title across lines instead of truncating to one line", () => {
+    const html = todoCard(makeTodo({ title: "A very long issue title that should wrap across more than one line of text" }));
+    expect(html).toContain("-webkit-line-clamp:2");
+    expect(html).not.toContain("text-overflow:ellipsis");
+  });
 });
 
 // ── full render() — My Work screen composition ──────────────────────────────
@@ -243,4 +255,15 @@ describe("render() — My Work screen", () => {
     const html = render(stateWithDashboard(data, false));
     expect(html).not.toContain('data-act="adminBackfill"');
   });
+
+  it("renders To-do before Previous activity", () => {
+    const data: DashboardData = {
+      person: "alice",
+      previousActivity: [makePr({ summary: null })],
+      todo: [makeTodo()],
+      degraded: false,
+    };
+    const html = render(stateWithDashboard(data));
+    expect(html.indexOf("To-do")).toBeLessThan(html.indexOf("Previous activity"));
+  });
 });
diff --git a/web/src/render.ts b/web/src/render.ts
index 5f3b818..d388b8c 100644
--- a/web/src/render.ts
+++ b/web/src/render.ts
@@ -1396,15 +1396,21 @@ export function prActivityCard(pr: MyWorkPr, markdownFn: (body: string) => strin
   </div>`;
 }
 
-/** An assigned-issue card — priority + #number + title + up-to-3 labels, no markdown. */
+/** An assigned-issue card — priority + #number + title (wraps up to 2 lines) on
+ *  row 1, labels (capped at 3) + relative updated-at on row 2. No markdown. */
 export function todoCard(t: MyWorkTodo): string {
   const prio = t.priority ? `<span style="font-size:10.5px;font-weight:700;font-family:var(--mono);color:var(--amber);flex:none">${esc(t.priority)}</span>` : "";
   const labels = t.labels.slice(0, 3).map((l) => `<span style="font-size:10.5px;color:var(--fg-40);border:1px solid var(--border);border-radius:5px;padding:1px 6px">${esc(l)}</span>`).join("");
-  return `<a href="${attr(safeUrl(t.url))}" target="_blank" rel="noopener" class="cnpy-card" style="display:flex;align-items:center;gap:11px;border:1px solid var(--border);border-radius:10px;padding:11px 14px;text-decoration:none;color:var(--fg)">
-    ${prio}
-    <span style="font-family:var(--mono);font-size:12px;color:var(--fg-40);flex:none">#${t.number}</span>
-    <span style="flex:1;font-size:13.5px;min-width:0;overflow:hidden;text-overflow:ellipsis;white-space:nowrap">${esc(t.title)}</span>
-    <span style="display:flex;gap:5px;flex:none">${labels}</span>
+  return `<a href="${attr(safeUrl(t.url))}" target="_blank" rel="noopener" class="cnpy-card" style="display:flex;flex-direction:column;gap:6px;border:1px solid var(--border);border-radius:10px;padding:11px 14px;text-decoration:none;color:var(--fg)">
+    <div style="display:flex;align-items:baseline;gap:9px">
+      ${prio}
+      <span style="font-family:var(--mono);font-size:12px;color:var(--fg-40);flex:none">#${t.number}</span>
+      <span style="font-size:13.5px;line-height:1.4;display:-webkit-box;-webkit-line-clamp:2;-webkit-box-orient:vertical;overflow:hidden">${esc(t.title)}</span>
+    </div>
+    <div style="display:flex;align-items:center;gap:5px">
+      <span style="display:flex;gap:5px;flex:1;min-width:0">${labels}</span>
+      <span style="font-size:11px;color:var(--fg-40);flex:none">${relTime(t.updatedAt)}</span>
+    </div>
   </a>`;
 }
 
@@ -1435,7 +1441,7 @@ function myWorkView(s: AppState): string {
   const activity = mwSection("Previous activity", activityBody);
   const todo = mwSection("To-do", todoBody);
 
-  return wrapMyWork(`${hero}${activity}${todo}`);
+  return wrapMyWork(`${hero}${todo}${activity}`);
 }
 
 // ── root ─────────────────────────────────────────────────────────────────────

From 279583ed2f6b539909f795d7f9780ab9eb30553f Mon Sep 17 00:00:00 2001
From: AndresL230 <190146319+AndresL230@users.noreply.github.com>
Date: Fri, 3 Jul 2026 16:03:50 -0400
Subject: [PATCH 7/9] feat(backfill): retroactively resync PR summaries to the
 structured format; drop the 14-day window

---
 src/tools/backfill.ts | 50 +++++++++++++-----------
 test/backfill.test.ts | 91 +++++++++++++++++++++++++++++++------------
 web/src/api.ts        |  2 +-
 web/src/main.ts       |  2 +-
 web/src/render.ts     |  2 +-
 5 files changed, 97 insertions(+), 50 deletions(-)

diff --git a/src/tools/backfill.ts b/src/tools/backfill.ts
index 914f975..8a482bb 100644
--- a/src/tools/backfill.ts
+++ b/src/tools/backfill.ts
@@ -1,9 +1,11 @@
 import type { Env } from "../env";
-import { nowIso } from "../db";
+import type { PrSummaryRow } from "@shared/rows";
+import { first } from "../db";
 import { ingestEvent } from "../consumer";
 import { eventsFromDelivery } from "../webhook";
 import { type Summarizer, workersAiSummarizer, storePrSummary } from "./summarize";
 import { applyEventProgress } from "./progress";
+import { parseStructuredSummary } from "@shared/prSummary";
 
 // Admin-triggered server-side GitHub backfill. Unlike scripts/backfill-events.mjs
 // (which signs synthetic webhook deliveries with the webhook secret), this runs
@@ -19,13 +21,13 @@ import { applyEventProgress } from "./progress";
 
 const GH_API = "application/vnd.github+json";
 const USER_AGENT = "canopy";
-const DAYS_BACK = 14;
 
 export interface BackfillResult {
   ok: boolean;
   error?: string;
   captured: number;
   unchanged: number;
+  summarized: number;
   prs: number;
   issues: number;
 }
@@ -120,12 +122,12 @@ function issueDelivery(issue: GhIssueListItem) {
 export async function runBackfill(
   env: Env,
   principalLogin: string,
-  opts?: { fetchImpl?: typeof fetch; summarizer?: Summarizer | null; now?: string }
+  opts?: { fetchImpl?: typeof fetch; summarizer?: Summarizer | null }
 ): Promise<BackfillResult> {
   const token = env.GITHUB_SERVICE_TOKEN;
   const repo = env.GITHUB_REPO;
   if (!token || !repo) {
-    return { ok: false, error: "service token or repo not configured", captured: 0, unchanged: 0, prs: 0, issues: 0 };
+    return { ok: false, error: "service token or repo not configured", captured: 0, unchanged: 0, summarized: 0, prs: 0, issues: 0 };
   }
 
   const doFetch = opts?.fetchImpl ?? fetch;
@@ -136,26 +138,18 @@ export async function runBackfill(
     "user-agent": USER_AGENT,
     "x-github-api-version": "2022-11-28",
   };
-  const cutoffMs = new Date(opts?.now ?? nowIso()).getTime() - DAYS_BACK * 24 * 60 * 60 * 1000;
 
-  // (a) Closed PRs updated in the last 14 days. Sorted updated-desc, so we stop
-  //     paginating at the first item whose updated_at predates the cutoff.
+  // (a) All closed PRs, fully paginated — full history, not just recent
+  //     activity, so a Sync also surfaces PRs merged before this route existed.
   const prList: GhPrListItem[] = [];
   {
     let url: string | null = `https://api.github.com/repos/${repo}/pulls?state=closed&sort=updated&direction=desc&per_page=100`;
-    let done = false;
-    while (url && !done) {
+    while (url) {
       const res: Response = await doFetch(url, { headers });
       if (!res.ok) break;
       const page = (await res.json()) as GhPrListItem[];
-      for (const pr of page) {
-        if (pr.updated_at && new Date(pr.updated_at).getTime() < cutoffMs) {
-          done = true;
-          break;
-        }
-        prList.push(pr);
-      }
-      url = done ? null : nextLink(res);
+      prList.push(...page);
+      url = nextLink(res);
     }
   }
 
@@ -178,6 +172,7 @@ export async function runBackfill(
 
   let captured = 0;
   let unchanged = 0;
+  let summarized = 0;
 
   for (const pr of prList) {
     const payload = prClosedDelivery(pr);
@@ -186,8 +181,20 @@ export async function runBackfill(
       const res = await ingestEvent(env.DB, ev, principalLogin);
       if (res.outcome === "written") {
         captured++;
-        // Mirror handleGithubWebhook's summary seam: parse THIS PR's own raw and
-        // store a capture-time summary (storePrSummary never throws).
+      } else {
+        unchanged++;
+      }
+
+      // (Re)summarize unless it's already in the structured format — decoupled
+      // from the event-capture outcome so a Sync also migrates PRs captured
+      // before the structured format existed, not just brand-new ones.
+      const existing = await first<PrSummaryRow>(
+        env.DB,
+        `SELECT summary FROM pr_summaries WHERE semantic_key = ?`,
+        ev.semantic_key
+      );
+      const alreadyStructured = existing !== null && parseStructuredSummary(existing.summary) !== null;
+      if (!alreadyStructured) {
         const parsed = JSON.parse(ev.raw) as { pr: { number: number; title: string; body: string | null } };
         await storePrSummary(env.DB, summarizer, {
           semantic_key: ev.semantic_key,
@@ -195,8 +202,7 @@ export async function runBackfill(
           title: parsed.pr.title,
           body: parsed.pr.body ?? "",
         });
-      } else {
-        unchanged++;
+        summarized++;
       }
     }
   }
@@ -216,5 +222,5 @@ export async function runBackfill(
     }
   }
 
-  return { ok: true, captured, unchanged, prs: prList.length, issues: issueList.length };
+  return { ok: true, captured, unchanged, summarized, prs: prList.length, issues: issueList.length };
 }
diff --git a/test/backfill.test.ts b/test/backfill.test.ts
index 17294bf..bc4a324 100644
--- a/test/backfill.test.ts
+++ b/test/backfill.test.ts
@@ -6,10 +6,6 @@ import type { Env } from "../src/env";
 import type { Summarizer } from "../src/tools/summarize";
 import type { EventRow, PrSummaryRow } from "@shared/rows";
 
-// Fixed "now" so the 14-day window is deterministic. threeDaysAgo is inside the
-// window; twentyDaysAgo is outside it (must be excluded — and, being sorted
-// updated-desc, must also stop pagination).
-const NOW = "2026-07-01T00:00:00Z";
 const threeDaysAgo = "2026-06-28T00:00:00Z";
 const twentyDaysAgo = "2026-06-11T00:00:00Z";
 
@@ -24,8 +20,19 @@ function stubFetch(prs: unknown[], issues: unknown[]): typeof fetch {
   }) as unknown as typeof fetch;
 }
 
-// Deterministic summarizer stub — never touches Workers AI.
-const summarizer: Summarizer = { model: "test-model", summarize: async () => "AI summary" };
+// Deterministic summarizer stub — never touches Workers AI. Counts calls so
+// tests can assert the retroactive-resummarize / skip-if-structured behavior.
+function countingSummarizer(summary: string): Summarizer & { calls: number } {
+  const s = {
+    model: "test-model",
+    calls: 0,
+    async summarize() {
+      s.calls++;
+      return summary;
+    },
+  };
+  return s;
+}
 
 function envWith(overrides: Partial<Env> = {}): Env {
   return { ...(env as unknown as Env), GITHUB_SERVICE_TOKEN: "svc-token", GITHUB_REPO: "o/r", ...overrides };
@@ -42,14 +49,14 @@ const mergedPr = {
   user: { login: "octocat" },
   milestone: null,
 };
-const oldPr = {
+const olderPr = {
   number: 5,
   title: "Old PR",
   body: "old",
   html_url: "https://github.com/o/r/pull/5",
   merged_at: twentyDaysAgo,
   closed_at: twentyDaysAgo,
-  updated_at: twentyDaysAgo, // predates the cutoff → excluded (and stops pagination)
+  updated_at: twentyDaysAgo, // older than the old 14-day window — now included too (full history, no cutoff)
   user: { login: "octocat" },
   milestone: null,
 };
@@ -78,21 +85,22 @@ const prAsIssue = {
 };
 
 describe("runBackfill", () => {
-  it("captures in-window closed PRs + open issues as backfill events written by the admin principal", async () => {
+  it("captures ALL closed PRs (full history, no recency window) + open issues, written by the admin principal", async () => {
+    const summarizer = countingSummarizer("AI summary");
     const res = await runBackfill(envWith(), "admin-user", {
-      fetchImpl: stubFetch([mergedPr, oldPr], [openIssue, prAsIssue]),
+      fetchImpl: stubFetch([mergedPr, olderPr], [openIssue, prAsIssue]),
       summarizer,
-      now: NOW,
     });
 
     expect(res.ok).toBe(true);
-    expect(res.prs).toBe(1); // oldPr excluded by the 14-day window
+    expect(res.prs).toBe(2); // both mergedPr and olderPr — no cutoff anymore
     expect(res.issues).toBe(1); // prAsIssue excluded (pull_request present)
-    expect(res.captured).toBe(2);
+    expect(res.captured).toBe(3); // 2 PR events + 1 issue event
     expect(res.unchanged).toBe(0);
+    expect(res.summarized).toBe(2); // one summary per newly-captured PR
 
     const events = await all<EventRow>(env.DB, `SELECT * FROM events ORDER BY ref_number`);
-    expect(events).toHaveLength(2);
+    expect(events).toHaveLength(3);
     for (const ev of events) {
       expect(ev.provenance).toBe("backfill"); // provenance post-mapped from "webhook"
       expect(ev.recorded_by).toBe("admin-user"); // writer is the ADMIN principal, not "github-webhook"
@@ -102,33 +110,66 @@ describe("runBackfill", () => {
     expect(pr.event_type).toBe("pr_merged");
     expect(pr.subject_login).toBe("octocat");
 
-    // The PR summary projection ran for the newly-written PR event.
+    // The PR summary projection ran for both newly-written PR events.
     const summary = await first<PrSummaryRow>(env.DB, `SELECT * FROM pr_summaries WHERE pr_number = ?`, 10);
     expect(summary).toBeTruthy();
     expect(summary?.summary).toBe("AI summary");
   });
 
-  it("is idempotent — a second run over the same GitHub state writes nothing new", async () => {
+  it("is idempotent on event capture — a second run over the same GitHub state writes no new events", async () => {
+    const summarizer = countingSummarizer("**What changed:** AI summary");
     const fetchImpl = stubFetch([mergedPr], [openIssue]);
-    const first = await runBackfill(envWith(), "admin-user", { fetchImpl, summarizer, now: NOW });
-    expect(first.captured).toBe(2);
+    const firstRun = await runBackfill(envWith(), "admin-user", { fetchImpl, summarizer });
+    expect(firstRun.captured).toBe(2);
 
-    const second = await runBackfill(envWith(), "admin-user", { fetchImpl, summarizer, now: NOW });
-    expect(second.ok).toBe(true);
-    expect(second.captured).toBe(0);
-    expect(second.unchanged).toBe(2);
+    const secondRun = await runBackfill(envWith(), "admin-user", { fetchImpl, summarizer });
+    expect(secondRun.ok).toBe(true);
+    expect(secondRun.captured).toBe(0);
+    expect(secondRun.unchanged).toBe(2);
     expect(await all(env.DB, `SELECT * FROM events`)).toHaveLength(2); // INSERT OR IGNORE on semantic_key
   });
 
+  it("retroactively re-summarizes a PR whose existing summary is NOT structured", async () => {
+    const plainSummarizer = countingSummarizer("Plain prose summary, not structured.");
+    const fetchImpl = stubFetch([mergedPr], []);
+    const firstRun = await runBackfill(envWith(), "admin-user", { fetchImpl, summarizer: plainSummarizer });
+    expect(firstRun.summarized).toBe(1);
+    expect(plainSummarizer.calls).toBe(1);
+
+    // Second run: the event is unchanged, but the stored summary is still
+    // plain prose (doesn't match the structured convention) → re-summarized.
+    const secondRun = await runBackfill(envWith(), "admin-user", { fetchImpl, summarizer: plainSummarizer });
+    expect(secondRun.captured).toBe(0);
+    expect(secondRun.unchanged).toBe(1);
+    expect(secondRun.summarized).toBe(1);
+    expect(plainSummarizer.calls).toBe(2);
+  });
+
+  it("skips re-summarizing a PR whose existing summary is already structured", async () => {
+    const structuredSummarizer = countingSummarizer("**What changed:** Fixed the thing.");
+    const fetchImpl = stubFetch([mergedPr], []);
+    const firstRun = await runBackfill(envWith(), "admin-user", { fetchImpl, summarizer: structuredSummarizer });
+    expect(firstRun.summarized).toBe(1);
+    expect(structuredSummarizer.calls).toBe(1);
+
+    // Second run: the stored summary already matches the structured convention
+    // → skipped, no second summarizer call.
+    const secondRun = await runBackfill(envWith(), "admin-user", { fetchImpl, summarizer: structuredSummarizer });
+    expect(secondRun.summarized).toBe(0);
+    expect(structuredSummarizer.calls).toBe(1);
+
+    const summary = await first<PrSummaryRow>(env.DB, `SELECT * FROM pr_summaries WHERE pr_number = ?`, 10);
+    expect(summary?.summary).toBe("**What changed:** Fixed the thing.");
+  });
+
   it("returns {ok:false} (no throw, no writes) when the service token is missing", async () => {
     const res = await runBackfill(envWith({ GITHUB_SERVICE_TOKEN: undefined }), "admin-user", {
       fetchImpl: stubFetch([mergedPr], [openIssue]),
-      summarizer,
-      now: NOW,
+      summarizer: countingSummarizer("AI summary"),
     });
     expect(res.ok).toBe(false);
     expect(res.error).toContain("service token or repo");
-    expect(res).toMatchObject({ captured: 0, unchanged: 0, prs: 0, issues: 0 });
+    expect(res).toMatchObject({ captured: 0, unchanged: 0, summarized: 0, prs: 0, issues: 0 });
     expect(await all(env.DB, `SELECT * FROM events`)).toHaveLength(0);
   });
 });
diff --git a/web/src/api.ts b/web/src/api.ts
index cbcd9a5..40cc3ca 100644
--- a/web/src/api.ts
+++ b/web/src/api.ts
@@ -126,7 +126,7 @@ export function getMe(): Promise<Me> {
 
 // ADMIN action: trigger the server-side GitHub backfill (admin-only route). The
 // worker holds the service token and fetches GitHub directly — no webhook secret.
-export function adminBackfill(): Promise<{ ok: boolean; captured: number; unchanged: number; prs: number; issues: number }> {
+export function adminBackfill(): Promise<{ ok: boolean; captured: number; unchanged: number; summarized: number; prs: number; issues: number }> {
   return postJson("/admin/backfill", {});
 }
 
diff --git a/web/src/main.ts b/web/src/main.ts
index ff5f655..bf4fdf5 100644
--- a/web/src/main.ts
+++ b/web/src/main.ts
@@ -482,7 +482,7 @@ function dispatch(act: string, arg: string | null, value: string | null): void {
     case "adminBackfill": {
       flash("Syncing GitHub&hellip;");
       adminBackfill()
-        .then((r) => { flash(`Synced: ${r.captured} captured, ${r.unchanged} unchanged`); loadMyWork(); })
+        .then((r) => { flash(`Synced: ${r.captured} captured, ${r.unchanged} unchanged, ${r.summarized} summaries updated`); loadMyWork(); })
         .catch((e) => {
           if (e instanceof Unauthorized) { state.view = "auth"; state.authStep = "login"; rerender(); return; }
           flash(e instanceof ApiError ? e.message : "Sync failed");
diff --git a/web/src/render.ts b/web/src/render.ts
index d388b8c..2e14f56 100644
--- a/web/src/render.ts
+++ b/web/src/render.ts
@@ -340,7 +340,7 @@ function header(s: AppState): string {
   // ADMIN-only, My Work screen: trigger the server-side GitHub backfill. Rendered
   // only when /auth/me returned admin:true (outline button, promote-class action).
   const myworkControls = s.screen === "mywork" && s.me?.admin
-    ? `<button data-act="adminBackfill" title="Fetch recent GitHub PRs + issues" class="cnpy-outlinebtn" style="display:flex;align-items:center;gap:7px;padding:6px 12px;border-radius:8px;border:1px solid var(--border-strong);font-size:12.5px;font-weight:500;color:var(--fg-70)">
+    ? `<button data-act="adminBackfill" title="Fetch all GitHub PRs + issues" class="cnpy-outlinebtn" style="display:flex;align-items:center;gap:7px;padding:6px 12px;border-radius:8px;border:1px solid var(--border-strong);font-size:12.5px;font-weight:500;color:var(--fg-70)">
       <svg width="15" height="15" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="1.8"><path d="M21 12a9 9 0 1 1-3-6.7L21 8"></path><path d="M21 3v5h-5"></path></svg>
       Sync GitHub
     </button>` : "";

From 2fa5ae9961a75eb952d77bffc6eb38fdf61464ea Mon Sep 17 00:00:00 2001
From: AndresL230 <190146319+AndresL230@users.noreply.github.com>
Date: Fri, 3 Jul 2026 16:19:22 -0400
Subject: [PATCH 8/9] fix(shared): tolerate a leading AI preamble before the
 What changed marker
MIME-Version: 1.0
Content-Type: text/plain; charset=UTF-8
Content-Transfer-Encoding: 8bit

STRUCTURED_RE was anchored with ^\s* at the start of the string, so an
8B instruct model prepending a preamble like "Here's the summary:"
caused parseStructuredSummary to return null even though the
structured content was present later — the PR silently fell back to
prose rendering and the backfill re-summarized it on every future
click. Drop the start-of-string anchor; the trailing $ still requires
everything after the marker to be consumed as what/why content.
---
 shared/prSummary.ts    | 2 +-
 test/prSummary.test.ts | 8 ++++++++
 2 files changed, 9 insertions(+), 1 deletion(-)

diff --git a/shared/prSummary.ts b/shared/prSummary.ts
index bcb90d5..ffc762b 100644
--- a/shared/prSummary.ts
+++ b/shared/prSummary.ts
@@ -12,7 +12,7 @@ export interface StructuredPrSummary {
   why: string | null;
 }
 
-const STRUCTURED_RE = /^\s*\*\*What changed:\*\*\s*([\s\S]*?)(?:\s*\*\*Why:\*\*\s*([\s\S]*))?$/i;
+const STRUCTURED_RE = /\*\*What changed:\*\*\s*([\s\S]*?)(?:\s*\*\*Why:\*\*\s*([\s\S]*))?$/i;
 
 /** Parses "**What changed:** ... **Why:** ..." out of a PR summary's markdown.
  *  Returns null when the text doesn't match (old-style prose, the excerpt
diff --git a/test/prSummary.test.ts b/test/prSummary.test.ts
index 05176a6..6efb54b 100644
--- a/test/prSummary.test.ts
+++ b/test/prSummary.test.ts
@@ -43,4 +43,12 @@ describe("parseStructuredSummary", () => {
     const raw = "**What changed:** \n**Why:** something";
     expect(parseStructuredSummary(raw)).toBeNull();
   });
+
+  it("tolerates a leading preamble before the What changed marker (AI non-conformance)", () => {
+    const raw = "Here's the summary:\n\n**What changed:** Fixed the login bug.\n**Why:** Users were affected.";
+    expect(parseStructuredSummary(raw)).toEqual({
+      what: "Fixed the login bug.",
+      why: "Users were affected.",
+    });
+  });
 });

From 278e0357b5060eaa1cfa6f822059676a755e82cf Mon Sep 17 00:00:00 2001
From: AndresL230 <190146319+AndresL230@users.noreply.github.com>
Date: Fri, 3 Jul 2026 16:29:56 -0400
Subject: [PATCH 9/9] docs(plan): My Work reorder + structured cards +
 retroactive summary resync implementation plan

---
 .../2026-07-03-mywork-restructure-plan.md     | 955 ++++++++++++++++++
 1 file changed, 955 insertions(+)
 create mode 100644 docs/superpowers/plans/2026-07-03-mywork-restructure-plan.md

diff --git a/docs/superpowers/plans/2026-07-03-mywork-restructure-plan.md b/docs/superpowers/plans/2026-07-03-mywork-restructure-plan.md
new file mode 100644
index 0000000..97eebcb
--- /dev/null
+++ b/docs/superpowers/plans/2026-07-03-mywork-restructure-plan.md
@@ -0,0 +1,955 @@
+# My Work Restructure Implementation Plan
+
+> **For agentic workers:** REQUIRED SUB-SKILL: Use superpowers:subagent-driven-development (recommended) or superpowers:executing-plans to implement this plan task-by-task. Steps use checkbox (`- [ ]`) syntax for tracking.
+
+**Goal:** Reorder My Work so To-do renders above Previous activity, give both sections
+richer structured cards, and make the admin "Sync GitHub" backfill retroactively
+migrate every historical merged PR (not just brand-new ones) to the new structured
+summary format.
+
+**Architecture:** A new shared module (`shared/prSummary.ts`) defines a markdown
+convention (`**What changed:** ... **Why:** ...`) and a parser for it — the single
+source of truth both the Worker (to decide whether a PR summary needs regenerating)
+and the web build (to decide how to render it) import. No database migration: the
+structure lives in the markdown convention inside the existing `pr_summaries.summary`
+TEXT column, so old prose and the deterministic excerpt fallback degrade gracefully to
+today's plain rendering instead of erroring.
+
+**Tech Stack:** TypeScript, Cloudflare Workers (Hono), D1, Vitest + Miniflare, plain
+DOM-less server-rendered HTML strings (`web/src/render.ts`).
+
+## Global Constraints
+
+- Design source: `docs/superpowers/specs/2026-07-03-mywork-restructure-design.md`.
+- No new D1 migration — `pr_summaries.summary` stays a single `TEXT` column.
+- `shared/` is the only cross-layer import location (`@shared/...` alias) — new shared
+  logic goes there, never duplicated in `src/` and `web/` separately.
+- Backend tests run against real Miniflare D1 (`npx vitest run test/<file>.test.ts`);
+  GitHub I/O and the summarizer are dependency-injected (`fetchImpl`, `summarizer`) —
+  never hit the network in tests.
+- Frontend render tests are pure (no DOM/DOMPurify) — mirror the existing `mockMd`
+  pattern in `test/render.mywork.test.ts`.
+- Run `npm run typecheck` after any task touching `shared/` or crossing the
+  Worker/web boundary — it does not run as part of `npm test`.
+
+---
+
+### Task 1: Shared structured-summary parser
+
+**Files:**
+- Create: `shared/prSummary.ts`
+- Create: `test/prSummary.test.ts`
+
+**Interfaces:**
+- Produces: `interface StructuredPrSummary { what: string; why: string | null }` and
+  `function parseStructuredSummary(raw: string): StructuredPrSummary | null`, imported
+  as `@shared/prSummary` by Task 3 (frontend rendering) and Task 5 (backend backfill
+  skip-check).
+
+- [ ] **Step 1: Write the failing tests**
+
+Create `test/prSummary.test.ts`:
+
+```ts
+import { describe, it, expect } from "vitest";
+import { parseStructuredSummary } from "@shared/prSummary";
+
+describe("parseStructuredSummary", () => {
+  it("parses What changed + Why into separate fields", () => {
+    const raw = "**What changed:** Fixed the login bug.\n**Why:** Users were being logged out unexpectedly.";
+    expect(parseStructuredSummary(raw)).toEqual({
+      what: "Fixed the login bug.",
+      why: "Users were being logged out unexpectedly.",
+    });
+  });
+
+  it("parses What changed alone, why:null, when there is no Why line", () => {
+    const raw = "**What changed:** Fixed the login bug.";
+    expect(parseStructuredSummary(raw)).toEqual({ what: "Fixed the login bug.", why: null });
+  });
+
+  it("handles What changed and Why on the same line", () => {
+    const raw = "**What changed:** Fixed the login bug. **Why:** Users were affected.";
+    expect(parseStructuredSummary(raw)).toEqual({
+      what: "Fixed the login bug.",
+      why: "Users were affected.",
+    });
+  });
+
+  it("is case-insensitive on the labels", () => {
+    const raw = "**what changed:** Fixed the login bug.\n**why:** Users were affected.";
+    expect(parseStructuredSummary(raw)).toEqual({
+      what: "Fixed the login bug.",
+      why: "Users were affected.",
+    });
+  });
+
+  it("returns null for old-style prose with no convention", () => {
+    expect(parseStructuredSummary("Fixed a bug that was breaking the login flow.")).toBeNull();
+  });
+
+  it("returns null for empty input", () => {
+    expect(parseStructuredSummary("")).toBeNull();
+  });
+
+  it("returns null when the What field is empty even if a Why is present", () => {
+    const raw = "**What changed:** \n**Why:** something";
+    expect(parseStructuredSummary(raw)).toBeNull();
+  });
+});
+```
+
+- [ ] **Step 2: Run tests to verify they fail**
+
+Run: `npx vitest run test/prSummary.test.ts`
+Expected: FAIL — `@shared/prSummary` does not exist yet.
+
+- [ ] **Step 3: Write the implementation**
+
+Create `shared/prSummary.ts`:
+
+```ts
+// Recognizes the "What changed / Why" markdown convention emitted by the PR
+// summarizer (src/tools/summarize.ts) so both the Worker (the backfill's
+// already-structured check, src/tools/backfill.ts) and the web build (card
+// rendering, web/src/render.ts) agree on what counts as a structured summary.
+// No schema change backs this — pr_summaries.summary stays a single markdown
+// TEXT column; the structure lives in this convention, not a stored shape, so
+// old prose summaries and the deterministic excerpt fallback degrade
+// gracefully to a `null` parse instead of erroring.
+
+export interface StructuredPrSummary {
+  what: string;
+  why: string | null;
+}
+
+const STRUCTURED_RE = /^\s*\*\*What changed:\*\*\s*([\s\S]*?)(?:\s*\*\*Why:\*\*\s*([\s\S]*))?$/i;
+
+/** Parses "**What changed:** ... **Why:** ..." out of a PR summary's markdown.
+ *  Returns null when the text doesn't match (old-style prose, the excerpt
+ *  fallback, or a malformed AI response) — callers treat null as "render/treat
+ *  as plain prose," never as an error. */
+export function parseStructuredSummary(raw: string): StructuredPrSummary | null {
+  const m = raw.match(STRUCTURED_RE);
+  if (!m) return null;
+  const what = m[1].trim();
+  if (!what) return null;
+  const why = m[2]?.trim() || null;
+  return { what, why };
+}
+```
+
+- [ ] **Step 4: Run tests to verify they pass**
+
+Run: `npx vitest run test/prSummary.test.ts`
+Expected: PASS (7 tests)
+
+- [ ] **Step 5: Typecheck**
+
+Run: `npm run typecheck`
+Expected: no errors
+
+- [ ] **Step 6: Commit**
+
+```bash
+git add shared/prSummary.ts test/prSummary.test.ts
+git commit -m "feat(shared): parseStructuredSummary — What changed/Why markdown convention"
+```
+
+---
+
+### Task 2: Backend — structured summarizer prompt
+
+**Files:**
+- Modify: `src/tools/summarize.ts:16-45`
+- Modify: `test/summarize.test.ts:1-11` (import), append a new `describe` block
+
+**Interfaces:**
+- Consumes: nothing new.
+- Produces: exported `SUMMARIZER_SYSTEM_PROMPT` constant (the two-field shape it
+  requires is what Task 1's `parseStructuredSummary` recognizes — keep them in sync
+  if either changes). `workersAiSummarizer`'s exported signature is unchanged.
+
+- [ ] **Step 1: Write the failing test**
+
+In `test/summarize.test.ts`, change the import on line 7 from:
+
+```ts
+import { storePrSummary, excerptSummary } from "../src/tools/summarize";
+```
+
+to:
+
+```ts
+import { storePrSummary, excerptSummary, SUMMARIZER_SYSTEM_PROMPT } from "../src/tools/summarize";
+```
+
+Then append this block at the end of the file (after the `webhook → summarize wiring`
+`describe` block):
+
+```ts
+describe("SUMMARIZER_SYSTEM_PROMPT", () => {
+  it("requires the structured What changed / Why convention", () => {
+    expect(SUMMARIZER_SYSTEM_PROMPT).toContain("**What changed:**");
+    expect(SUMMARIZER_SYSTEM_PROMPT).toContain("**Why:**");
+  });
+});
+```
+
+- [ ] **Step 2: Run test to verify it fails**
+
+Run: `npx vitest run test/summarize.test.ts`
+Expected: FAIL — `SUMMARIZER_SYSTEM_PROMPT` is not exported yet.
+
+- [ ] **Step 3: Write the implementation**
+
+In `src/tools/summarize.ts`, replace lines 16-45 (from `const WORKERS_AI_MODEL = ...`
+through the end of `workersAiSummarizer`) with:
+
+```ts
+const WORKERS_AI_MODEL = "@cf/meta/llama-3.1-8b-instruct";
+
+// Exported for a content assertion in test/summarize.test.ts — the two-field
+// shape here is exactly what shared/prSummary.ts's parseStructuredSummary
+// recognizes; keep them in sync if either changes.
+export const SUMMARIZER_SYSTEM_PROMPT =
+  "Summarize this one pull request's description for a team activity feed. " +
+  "Respond with ONLY this exact markdown structure, nothing else:\n" +
+  "**What changed:** <1-2 short factual sentences>\n" +
+  "**Why:** <1 short sentence stating the description's own stated rationale>\n" +
+  'If the description states no rationale, omit the "**Why:**" line entirely. ' +
+  "Do not speculate beyond the text.";
+
+/** Workers AI-backed summarizer. Bounded to THAT PR's own title+body — no other
+ *  context is sent. Never throws: any failure (network, empty output, malformed
+ *  response) resolves to null so the caller falls back to excerptSummary. */
+export function workersAiSummarizer(ai: Ai): Summarizer {
+  return {
+    model: WORKERS_AI_MODEL,
+    async summarize({ title, body }) {
+      try {
+        const result = await ai.run(WORKERS_AI_MODEL, {
+          messages: [
+            { role: "system", content: SUMMARIZER_SYSTEM_PROMPT },
+            { role: "user", content: `Title: ${title}\n\nBody: ${body}` },
+          ],
+        });
+        const response = (result as { response?: unknown } | null)?.response;
+        if (typeof response !== "string") return null;
+        const trimmed = response.trim();
+        return trimmed.length > 0 ? trimmed : null;
+      } catch {
+        return null;
+      }
+    },
+  };
+}
+```
+
+- [ ] **Step 4: Run tests to verify they pass**
+
+Run: `npx vitest run test/summarize.test.ts`
+Expected: PASS (all tests, including the new one)
+
+- [ ] **Step 5: Commit**
+
+```bash
+git add src/tools/summarize.ts test/summarize.test.ts
+git commit -m "feat(summarize): require the What changed/Why structured markdown convention"
+```
+
+---
+
+### Task 3: Frontend — structured "Previous activity" cards
+
+**Files:**
+- Modify: `web/src/render.ts:10` (import), `:1331` (label style), `:1354-1375`
+  (`prActivityCard`)
+- Modify: `test/render.mywork.test.ts` — append cases to the `prActivityCard`
+  `describe` block
+
+**Interfaces:**
+- Consumes: `parseStructuredSummary`, `StructuredPrSummary` from `@shared/prSummary`
+  (Task 1).
+- Produces: `prActivityCard`'s exported signature is unchanged
+  (`(pr: MyWorkPr, markdownFn: (body: string) => string) => string`) — only its
+  internal rendering changes, so no other file needs to change its call site.
+
+- [ ] **Step 1: Write the failing tests**
+
+In `test/render.mywork.test.ts`, inside the existing `describe("prActivityCard", ...)`
+block, append these three tests (after the last existing `it(...)`, before the
+block's closing `});`):
+
+```ts
+  it("renders structured What changed + Why as separate labeled rows", () => {
+    const pr = makePr({ summary: "**What changed:** Fixed the login bug.\n**Why:** Users were logged out unexpectedly." });
+    const html = prActivityCard(pr, mockMd);
+    expect(html).toContain("What changed");
+    expect(html).toContain("Why");
+    expect(html).toContain("Fixed the login bug.");
+    expect(html).toContain("Users were logged out unexpectedly.");
+  });
+
+  it("omits the Why row when the structured summary has no Why", () => {
+    const pr = makePr({ summary: "**What changed:** Fixed the login bug." });
+    const html = prActivityCard(pr, mockMd);
+    expect(html).toContain("What changed");
+    expect(html).not.toContain("Why");
+  });
+
+  it("falls back to the raw prose block for a non-conforming summary (legacy/excerpt)", () => {
+    const pr = makePr({ summary: "Fixed the login bug that was affecting users." });
+    const html = prActivityCard(pr, mockMd);
+    expect(html).not.toContain("What changed");
+    expect(html).toContain("mock-md");
+  });
+```
+
+- [ ] **Step 2: Run tests to verify the new ones fail**
+
+Run: `npx vitest run test/render.mywork.test.ts`
+Expected: the 3 new tests FAIL (current `prActivityCard` always renders the raw
+prose block, never labeled rows); all pre-existing tests in the file still PASS.
+
+- [ ] **Step 3: Write the implementation**
+
+In `web/src/render.ts`, change the import block. Line 10 currently reads:
+
+```ts
+import type { DashboardData, MyWorkPr, MyWorkTodo } from "@shared/dashboard";
+```
+
+Add a new line directly after it:
+
+```ts
+import type { DashboardData, MyWorkPr, MyWorkTodo } from "@shared/dashboard";
+import { parseStructuredSummary, type StructuredPrSummary } from "@shared/prSummary";
+```
+
+Then, at line 1331, directly after the `MW_LABEL` constant, add:
+
+```ts
+const MW_LABEL = "font-size:11px;font-weight:600;font-family:var(--mono);text-transform:uppercase;letter-spacing:.1em;color:var(--fg-40)";
+const MW_FIELD_LABEL = "font-size:10px;font-weight:600;font-family:var(--mono);text-transform:uppercase;letter-spacing:.08em;color:var(--fg-40);margin-bottom:3px";
+```
+
+Then replace the whole `prActivityCard` function (lines 1354-1375, from the
+`/** A merged/closed PR card...` comment through its closing `}`) with:
+
+```ts
+/** Renders a structured {what, why} summary as labeled rows (small caption + markdown body each). */
+function structuredSummaryBody(structured: StructuredPrSummary, markdownFn: (body: string) => string): string {
+  const whatRow = `<div${structured.why ? ' style="margin-bottom:10px"' : ""}>
+      <div style="${MW_FIELD_LABEL}">What changed</div>
+      <div class="cnpy-md" style="font-size:13.5px;color:var(--fg-70)">${markdownFn(structured.what)}</div>
+    </div>`;
+  const whyRow = structured.why
+    ? `<div>
+      <div style="${MW_FIELD_LABEL}">Why</div>
+      <div class="cnpy-md" style="font-size:13.5px;color:var(--fg-70)">${markdownFn(structured.why)}</div>
+    </div>`
+    : "";
+  return whatRow + whyRow;
+}
+
+/** A merged/closed PR card: #number → pr.url, title, relTime, MERGED/CLOSED chip,
+ *  and a summary body — labeled "What changed"/"Why" rows when pr.summary matches
+ *  the structured convention, else the raw markdown blob (legacy/excerpt fallback). */
+export function prActivityCard(pr: MyWorkPr, markdownFn: (body: string) => string): string {
+  const chip = pr.merged
+    ? `<span style="font-size:9.5px;font-weight:600;font-family:var(--mono);letter-spacing:.03em;color:var(--green);border:1px solid color-mix(in srgb,var(--green) 45%,transparent);background:color-mix(in srgb,var(--green) 12%,transparent);border-radius:5px;padding:2px 6px;white-space:nowrap">MERGED</span>`
+    : `<span style="font-size:9.5px;font-weight:600;font-family:var(--mono);letter-spacing:.03em;color:var(--fg-40);border:1px solid var(--border);border-radius:5px;padding:2px 6px;white-space:nowrap">CLOSED</span>`;
+  const structured = pr.summary !== null ? parseStructuredSummary(pr.summary) : null;
+  const body = pr.summary === null
+    ? `<div style="font-size:13.5px;color:var(--fg-55);line-height:1.6">${linkifyRefs("No summary recorded for this PR.")}</div>`
+    : structured !== null
+      ? structuredSummaryBody(structured, markdownFn)
+      : `<div class="cnpy-md" style="font-size:13.5px;color:var(--fg-70)">${markdownFn(pr.summary)}</div>`;
+  return `<div class="cnpy-card" style="border:1px solid var(--border);border-radius:13px;padding:14px 16px;margin-bottom:10px">
+    <div style="display:flex;align-items:center;justify-content:space-between;gap:10px;margin-bottom:8px">
+      <div style="display:flex;align-items:center;gap:9px;min-width:0">
+        <a href="${attr(safeUrl(pr.url))}" target="_blank" rel="noopener" style="font-family:var(--mono);font-size:12px;color:var(--fg-40);text-decoration:none;flex:none">#${pr.number}</a>
+        <span style="font-size:14px;font-weight:500;color:var(--fg);min-width:0;overflow:hidden;text-overflow:ellipsis;white-space:nowrap">${esc(pr.title)}</span>
+      </div>
+      <div style="display:flex;align-items:center;gap:9px;flex:none">
+        ${chip}
+        <span style="font-size:11.5px;color:var(--fg-40)">${relTime(pr.occurredAt)}</span>
+      </div>
+    </div>
+    ${body}
+  </div>`;
+}
+```
+
+- [ ] **Step 4: Run tests to verify they pass**
+
+Run: `npx vitest run test/render.mywork.test.ts`
+Expected: PASS (all tests, including the 3 new ones and every pre-existing one —
+the default `makePr()` summary "Fixed **the thing** that was broken." doesn't match
+the structured convention, so it still falls into the prose-block path unchanged).
+
+- [ ] **Step 5: Typecheck**
+
+Run: `npm run typecheck`
+Expected: no errors
+
+- [ ] **Step 6: Commit**
+
+```bash
+git add web/src/render.ts test/render.mywork.test.ts
+git commit -m "feat(mywork): render structured What changed/Why PR summaries as labeled rows"
+```
+
+---
+
+### Task 4: Frontend — To-do card restructure + reorder
+
+**Files:**
+- Modify: `web/src/render.ts:1377-1387` (`todoCard`), `:1413-1416` (`myWorkView`
+  composition order)
+- Modify: `test/render.mywork.test.ts` — append cases to the `todoCard` and
+  `render() — My Work screen` `describe` blocks
+
+**Interfaces:**
+- Consumes: existing `relTime` helper (already in scope in `render.ts`).
+- Produces: `todoCard`'s exported signature is unchanged (`(t: MyWorkTodo) => string`).
+
+- [ ] **Step 1: Write the failing tests**
+
+In `test/render.mywork.test.ts`, inside `describe("todoCard", ...)`, append (after
+the last existing `it(...)`, before the block's closing `});`):
+
+```ts
+  it("shows a relative 'updated' time derived from t.updatedAt", () => {
+    const threeDaysAgo = new Date(Date.now() - 3 * 24 * 60 * 60 * 1000).toISOString();
+    const html = todoCard(makeTodo({ updatedAt: threeDaysAgo }));
+    expect(html).toContain("3d ago");
+  });
+
+  it("wraps a long title across lines instead of truncating to one line", () => {
+    const html = todoCard(makeTodo({ title: "A very long issue title that should wrap across more than one line of text" }));
+    expect(html).toContain("-webkit-line-clamp:2");
+    expect(html).not.toContain("text-overflow:ellipsis");
+  });
+```
+
+Inside `describe("render() — My Work screen", ...)`, append (after the last existing
+`it(...)`, before the block's closing `});`):
+
+```ts
+  it("renders To-do before Previous activity", () => {
+    const data: DashboardData = {
+      person: "alice",
+      previousActivity: [makePr({ summary: null })],
+      todo: [makeTodo()],
+      degraded: false,
+    };
+    const html = render(stateWithDashboard(data));
+    expect(html.indexOf("To-do")).toBeLessThan(html.indexOf("Previous activity"));
+  });
+```
+
+- [ ] **Step 2: Run tests to verify the new ones fail**
+
+Run: `npx vitest run test/render.mywork.test.ts`
+Expected: the 3 new tests FAIL (current `todoCard` has no updated-at and truncates
+via `white-space:nowrap`/`text-overflow:ellipsis`; `myWorkView` renders activity
+before todo). Pre-existing tests still PASS.
+
+- [ ] **Step 3: Write the implementation**
+
+In `web/src/render.ts`, replace `todoCard` (lines 1377-1387) with:
+
+```ts
+/** An assigned-issue card — priority + #number + title (wraps up to 2 lines) on
+ *  row 1, labels (capped at 3) + relative updated-at on row 2. No markdown. */
+export function todoCard(t: MyWorkTodo): string {
+  const prio = t.priority ? `<span style="font-size:10.5px;font-weight:700;font-family:var(--mono);color:var(--amber);flex:none">${esc(t.priority)}</span>` : "";
+  const labels = t.labels.slice(0, 3).map((l) => `<span style="font-size:10.5px;color:var(--fg-40);border:1px solid var(--border);border-radius:5px;padding:1px 6px">${esc(l)}</span>`).join("");
+  return `<a href="${attr(safeUrl(t.url))}" target="_blank" rel="noopener" class="cnpy-card" style="display:flex;flex-direction:column;gap:6px;border:1px solid var(--border);border-radius:10px;padding:11px 14px;text-decoration:none;color:var(--fg)">
+    <div style="display:flex;align-items:baseline;gap:9px">
+      ${prio}
+      <span style="font-family:var(--mono);font-size:12px;color:var(--fg-40);flex:none">#${t.number}</span>
+      <span style="font-size:13.5px;line-height:1.4;display:-webkit-box;-webkit-line-clamp:2;-webkit-box-orient:vertical;overflow:hidden">${esc(t.title)}</span>
+    </div>
+    <div style="display:flex;align-items:center;gap:5px">
+      <span style="display:flex;gap:5px;flex:1;min-width:0">${labels}</span>
+      <span style="font-size:11px;color:var(--fg-40);flex:none">${relTime(t.updatedAt)}</span>
+    </div>
+  </a>`;
+}
+```
+
+Then, in `myWorkView`, change the composition (lines 1413-1416) from:
+
+```ts
+  const activity = mwSection("Previous activity", activityBody);
+  const todo = mwSection("To-do", todoBody);
+
+  return wrapMyWork(`${hero}${activity}${todo}`);
+```
+
+to:
+
+```ts
+  const activity = mwSection("Previous activity", activityBody);
+  const todo = mwSection("To-do", todoBody);
+
+  return wrapMyWork(`${hero}${todo}${activity}`);
+```
+
+- [ ] **Step 4: Run tests to verify they pass**
+
+Run: `npx vitest run test/render.mywork.test.ts`
+Expected: PASS (all tests)
+
+- [ ] **Step 5: Typecheck**
+
+Run: `npm run typecheck`
+Expected: no errors
+
+- [ ] **Step 6: Commit**
+
+```bash
+git add web/src/render.ts test/render.mywork.test.ts
+git commit -m "feat(mywork): reorder To-do above Previous activity; richer To-do cards"
+```
+
+---
+
+### Task 5: Backend — retroactive resync in Sync GitHub
+
+**Files:**
+- Modify: `src/tools/backfill.ts:1-6` (imports), `:22` (remove `DAYS_BACK`),
+  `:24-31` (`BackfillResult`), `:120-219` (`runBackfill`)
+- Modify: `test/backfill.test.ts` (full rewrite of fixtures/tests below)
+- Modify: `web/src/api.ts:129` (`adminBackfill` return type)
+- Modify: `web/src/main.ts:482-491` (`adminBackfill` flash message)
+- Modify: `web/src/render.ts:342` (Sync GitHub button title text)
+
+**Interfaces:**
+- Consumes: `parseStructuredSummary` from `@shared/prSummary` (Task 1).
+- Produces: `BackfillResult` gains `summarized: number`; `runBackfill`'s `opts` no
+  longer accepts `now` (it had no purpose once the recency cutoff is removed).
+
+- [ ] **Step 1: Rewrite the failing tests**
+
+Replace the entire contents of `test/backfill.test.ts` with:
+
+```ts
+import { describe, it, expect } from "vitest";
+import { env } from "cloudflare:test";
+import { all, first } from "../src/db";
+import { runBackfill } from "../src/tools/backfill";
+import type { Env } from "../src/env";
+import type { Summarizer } from "../src/tools/summarize";
+import type { EventRow, PrSummaryRow } from "@shared/rows";
+
+const threeDaysAgo = "2026-06-28T00:00:00Z";
+const twentyDaysAgo = "2026-06-11T00:00:00Z";
+
+// A Response-level fetch stub (the pool exports no fetch mock) — mirrors
+// test/roadmap.test.ts / test/progress.test.ts. Routes by path substring: the
+// pulls list vs the issues list.
+function stubFetch(prs: unknown[], issues: unknown[]): typeof fetch {
+  return (async (url: string | URL | Request) => {
+    const u = String(url);
+    const body = u.includes("/pulls") ? prs : u.includes("/issues") ? issues : [];
+    return new Response(JSON.stringify(body), { status: 200, headers: { "content-type": "application/json" } });
+  }) as unknown as typeof fetch;
+}
+
+// Deterministic summarizer stub — never touches Workers AI. Counts calls so
+// tests can assert the retroactive-resummarize / skip-if-structured behavior.
+function countingSummarizer(summary: string): Summarizer & { calls: number } {
+  const s = {
+    model: "test-model",
+    calls: 0,
+    async summarize() {
+      s.calls++;
+      return summary;
+    },
+  };
+  return s;
+}
+
+function envWith(overrides: Partial<Env> = {}): Env {
+  return { ...(env as unknown as Env), GITHUB_SERVICE_TOKEN: "svc-token", GITHUB_REPO: "o/r", ...overrides };
+}
+
+const mergedPr = {
+  number: 10,
+  title: "Add feature",
+  body: "This PR adds a feature.",
+  html_url: "https://github.com/o/r/pull/10",
+  merged_at: threeDaysAgo, // merged → derived merged:true from merged_at != null
+  closed_at: threeDaysAgo,
+  updated_at: threeDaysAgo,
+  user: { login: "octocat" },
+  milestone: null,
+};
+const olderPr = {
+  number: 5,
+  title: "Old PR",
+  body: "old",
+  html_url: "https://github.com/o/r/pull/5",
+  merged_at: twentyDaysAgo,
+  closed_at: twentyDaysAgo,
+  updated_at: twentyDaysAgo, // older than the old 14-day window — now included too (full history, no cutoff)
+  user: { login: "octocat" },
+  milestone: null,
+};
+const openIssue = {
+  number: 20,
+  title: "Fix bug",
+  html_url: "https://github.com/o/r/issues/20",
+  state: "open",
+  updated_at: threeDaysAgo,
+  user: { login: "octocat" },
+  assignees: [{ login: "octocat" }], // has an assignee → "assigned"
+  labels: ["bug"],
+  milestone: null,
+};
+const prAsIssue = {
+  number: 21,
+  title: "A PR the issues endpoint also returned",
+  html_url: "https://github.com/o/r/pull/21",
+  state: "open",
+  updated_at: threeDaysAgo,
+  user: { login: "octocat" },
+  pull_request: { url: "https://api.github.com/repos/o/r/pulls/21" }, // → skipped
+  assignees: [],
+  labels: [],
+  milestone: null,
+};
+
+describe("runBackfill", () => {
+  it("captures ALL closed PRs (full history, no recency window) + open issues, written by the admin principal", async () => {
+    const summarizer = countingSummarizer("AI summary");
+    const res = await runBackfill(envWith(), "admin-user", {
+      fetchImpl: stubFetch([mergedPr, olderPr], [openIssue, prAsIssue]),
+      summarizer,
+    });
+
+    expect(res.ok).toBe(true);
+    expect(res.prs).toBe(2); // both mergedPr and olderPr — no cutoff anymore
+    expect(res.issues).toBe(1); // prAsIssue excluded (pull_request present)
+    expect(res.captured).toBe(3); // 2 PR events + 1 issue event
+    expect(res.unchanged).toBe(0);
+    expect(res.summarized).toBe(2); // one summary per newly-captured PR
+
+    const events = await all<EventRow>(env.DB, `SELECT * FROM events ORDER BY ref_number`);
+    expect(events).toHaveLength(3);
+    for (const ev of events) {
+      expect(ev.provenance).toBe("backfill"); // provenance post-mapped from "webhook"
+      expect(ev.recorded_by).toBe("admin-user"); // writer is the ADMIN principal, not "github-webhook"
+    }
+    // The merged PR was captured as pr_merged (merged_at != null).
+    const pr = events.find((e) => e.ref_number === 10)!;
+    expect(pr.event_type).toBe("pr_merged");
+    expect(pr.subject_login).toBe("octocat");
+
+    // The PR summary projection ran for both newly-written PR events.
+    const summary = await first<PrSummaryRow>(env.DB, `SELECT * FROM pr_summaries WHERE pr_number = ?`, 10);
+    expect(summary).toBeTruthy();
+    expect(summary?.summary).toBe("AI summary");
+  });
+
+  it("is idempotent on event capture — a second run over the same GitHub state writes no new events", async () => {
+    const summarizer = countingSummarizer("**What changed:** AI summary");
+    const fetchImpl = stubFetch([mergedPr], [openIssue]);
+    const firstRun = await runBackfill(envWith(), "admin-user", { fetchImpl, summarizer });
+    expect(firstRun.captured).toBe(2);
+
+    const secondRun = await runBackfill(envWith(), "admin-user", { fetchImpl, summarizer });
+    expect(secondRun.ok).toBe(true);
+    expect(secondRun.captured).toBe(0);
+    expect(secondRun.unchanged).toBe(2);
+    expect(await all(env.DB, `SELECT * FROM events`)).toHaveLength(2); // INSERT OR IGNORE on semantic_key
+  });
+
+  it("retroactively re-summarizes a PR whose existing summary is NOT structured", async () => {
+    const plainSummarizer = countingSummarizer("Plain prose summary, not structured.");
+    const fetchImpl = stubFetch([mergedPr], []);
+    const firstRun = await runBackfill(envWith(), "admin-user", { fetchImpl, summarizer: plainSummarizer });
+    expect(firstRun.summarized).toBe(1);
+    expect(plainSummarizer.calls).toBe(1);
+
+    // Second run: the event is unchanged, but the stored summary is still
+    // plain prose (doesn't match the structured convention) → re-summarized.
+    const secondRun = await runBackfill(envWith(), "admin-user", { fetchImpl, summarizer: plainSummarizer });
+    expect(secondRun.captured).toBe(0);
+    expect(secondRun.unchanged).toBe(1);
+    expect(secondRun.summarized).toBe(1);
+    expect(plainSummarizer.calls).toBe(2);
+  });
+
+  it("skips re-summarizing a PR whose existing summary is already structured", async () => {
+    const structuredSummarizer = countingSummarizer("**What changed:** Fixed the thing.");
+    const fetchImpl = stubFetch([mergedPr], []);
+    const firstRun = await runBackfill(envWith(), "admin-user", { fetchImpl, summarizer: structuredSummarizer });
+    expect(firstRun.summarized).toBe(1);
+    expect(structuredSummarizer.calls).toBe(1);
+
+    // Second run: the stored summary already matches the structured convention
+    // → skipped, no second summarizer call.
+    const secondRun = await runBackfill(envWith(), "admin-user", { fetchImpl, summarizer: structuredSummarizer });
+    expect(secondRun.summarized).toBe(0);
+    expect(structuredSummarizer.calls).toBe(1);
+
+    const summary = await first<PrSummaryRow>(env.DB, `SELECT * FROM pr_summaries WHERE pr_number = ?`, 10);
+    expect(summary?.summary).toBe("**What changed:** Fixed the thing.");
+  });
+
+  it("returns {ok:false} (no throw, no writes) when the service token is missing", async () => {
+    const res = await runBackfill(envWith({ GITHUB_SERVICE_TOKEN: undefined }), "admin-user", {
+      fetchImpl: stubFetch([mergedPr], [openIssue]),
+      summarizer: countingSummarizer("AI summary"),
+    });
+    expect(res.ok).toBe(false);
+    expect(res.error).toContain("service token or repo");
+    expect(res).toMatchObject({ captured: 0, unchanged: 0, summarized: 0, prs: 0, issues: 0 });
+    expect(await all(env.DB, `SELECT * FROM events`)).toHaveLength(0);
+  });
+});
+```
+
+- [ ] **Step 2: Run tests to verify they fail**
+
+Run: `npx vitest run test/backfill.test.ts`
+Expected: FAIL — `res.summarized` is `undefined` (not yet on `BackfillResult`); the
+14-day-window assertion (`res.prs).toBe(2)`) also fails against current behavior.
+
+- [ ] **Step 3: Write the implementation**
+
+In `src/tools/backfill.ts`, replace the import block (lines 1-6) with:
+
+```ts
+import type { Env } from "../env";
+import type { PrSummaryRow } from "@shared/rows";
+import { first } from "../db";
+import { ingestEvent } from "../consumer";
+import { eventsFromDelivery } from "../webhook";
+import { type Summarizer, workersAiSummarizer, storePrSummary } from "./summarize";
+import { applyEventProgress } from "./progress";
+import { parseStructuredSummary } from "@shared/prSummary";
+```
+
+Delete the `const DAYS_BACK = 14;` line (line 22).
+
+Replace the `BackfillResult` interface (lines 24-31) with:
+
+```ts
+export interface BackfillResult {
+  ok: boolean;
+  error?: string;
+  captured: number;
+  unchanged: number;
+  summarized: number;
+  prs: number;
+  issues: number;
+}
+```
+
+Replace the function signature and early return (lines 120-129) with:
+
+```ts
+export async function runBackfill(
+  env: Env,
+  principalLogin: string,
+  opts?: { fetchImpl?: typeof fetch; summarizer?: Summarizer | null }
+): Promise<BackfillResult> {
+  const token = env.GITHUB_SERVICE_TOKEN;
+  const repo = env.GITHUB_REPO;
+  if (!token || !repo) {
+    return { ok: false, error: "service token or repo not configured", captured: 0, unchanged: 0, summarized: 0, prs: 0, issues: 0 };
+  }
+```
+
+Replace the fetch setup block (lines 131-139) — this removes the `cutoffMs` line:
+
+```ts
+  const doFetch = opts?.fetchImpl ?? fetch;
+  const summarizer = opts?.summarizer ?? (env.AI ? workersAiSummarizer(env.AI) : null);
+  const headers = {
+    authorization: `Bearer ${token}`,
+    accept: GH_API,
+    "user-agent": USER_AGENT,
+    "x-github-api-version": "2022-11-28",
+  };
+```
+
+Replace the PR list fetch (lines 141-160) with:
+
+```ts
+  // (a) All closed PRs, fully paginated — full history, not just recent
+  //     activity, so a Sync also surfaces PRs merged before this route existed.
+  const prList: GhPrListItem[] = [];
+  {
+    let url: string | null = `https://api.github.com/repos/${repo}/pulls?state=closed&sort=updated&direction=desc&per_page=100`;
+    while (url) {
+      const res: Response = await doFetch(url, { headers });
+      if (!res.ok) break;
+      const page = (await res.json()) as GhPrListItem[];
+      prList.push(...page);
+      url = nextLink(res);
+    }
+  }
+```
+
+Replace the PR loop and its counters (lines 179-202) with:
+
+```ts
+  let captured = 0;
+  let unchanged = 0;
+  let summarized = 0;
+
+  for (const pr of prList) {
+    const payload = prClosedDelivery(pr);
+    for (const base of eventsFromDelivery("pull_request", payload)) {
+      const ev = { ...base, provenance: "backfill" as const };
+      const res = await ingestEvent(env.DB, ev, principalLogin);
+      if (res.outcome === "written") {
+        captured++;
+      } else {
+        unchanged++;
+      }
+
+      // (Re)summarize unless it's already in the structured format — decoupled
+      // from the event-capture outcome so a Sync also migrates PRs captured
+      // before the structured format existed, not just brand-new ones.
+      const existing = await first<PrSummaryRow>(
+        env.DB,
+        `SELECT summary FROM pr_summaries WHERE semantic_key = ?`,
+        ev.semantic_key
+      );
+      const alreadyStructured = existing !== null && parseStructuredSummary(existing.summary) !== null;
+      if (!alreadyStructured) {
+        const parsed = JSON.parse(ev.raw) as { pr: { number: number; title: string; body: string | null } };
+        await storePrSummary(env.DB, summarizer, {
+          semantic_key: ev.semantic_key,
+          pr_number: parsed.pr.number,
+          title: parsed.pr.title,
+          body: parsed.pr.body ?? "",
+        });
+        summarized++;
+      }
+    }
+  }
+```
+
+Leave the issues loop (originally lines 204-217) exactly as-is — issues are never
+summarized and already have no recency window.
+
+Replace the final return (originally line 219) with:
+
+```ts
+  return { ok: true, captured, unchanged, summarized, prs: prList.length, issues: issueList.length };
+```
+
+Then wire `summarized` through the web layer. In `web/src/api.ts`, change line 129
+from:
+
+```ts
+export function adminBackfill(): Promise<{ ok: boolean; captured: number; unchanged: number; prs: number; issues: number }> {
+```
+
+to:
+
+```ts
+export function adminBackfill(): Promise<{ ok: boolean; captured: number; unchanged: number; summarized: number; prs: number; issues: number }> {
+```
+
+In `web/src/main.ts`, change the `case "adminBackfill":` block (lines 482-491) from:
+
+```ts
+    case "adminBackfill": {
+      flash("Syncing GitHub&hellip;");
+      adminBackfill()
+        .then((r) => { flash(`Synced: ${r.captured} captured, ${r.unchanged} unchanged`); loadMyWork(); })
+        .catch((e) => {
+          if (e instanceof Unauthorized) { state.view = "auth"; state.authStep = "login"; rerender(); return; }
+          flash(e instanceof ApiError ? e.message : "Sync failed");
+        });
+      return;
+    }
+```
+
+to:
+
+```ts
+    case "adminBackfill": {
+      flash("Syncing GitHub&hellip;");
+      adminBackfill()
+        .then((r) => { flash(`Synced: ${r.captured} captured, ${r.unchanged} unchanged, ${r.summarized} summaries updated`); loadMyWork(); })
+        .catch((e) => {
+          if (e instanceof Unauthorized) { state.view = "auth"; state.authStep = "login"; rerender(); return; }
+          flash(e instanceof ApiError ? e.message : "Sync failed");
+        });
+      return;
+    }
+```
+
+In `web/src/render.ts`, on line 342, change:
+
+```ts
+    ? `<button data-act="adminBackfill" title="Fetch recent GitHub PRs + issues" class="cnpy-outlinebtn" style="display:flex;align-items:center;gap:7px;padding:6px 12px;border-radius:8px;border:1px solid var(--border-strong);font-size:12.5px;font-weight:500;color:var(--fg-70)">
+```
+
+to:
+
+```ts
+    ? `<button data-act="adminBackfill" title="Fetch all GitHub PRs + issues" class="cnpy-outlinebtn" style="display:flex;align-items:center;gap:7px;padding:6px 12px;border-radius:8px;border:1px solid var(--border-strong);font-size:12.5px;font-weight:500;color:var(--fg-70)">
+```
+
+- [ ] **Step 4: Run tests to verify they pass**
+
+Run: `npx vitest run test/backfill.test.ts`
+Expected: PASS (all 5 tests)
+
+- [ ] **Step 5: Typecheck**
+
+Run: `npm run typecheck`
+Expected: no errors
+
+- [ ] **Step 6: Commit**
+
+```bash
+git add src/tools/backfill.ts test/backfill.test.ts web/src/api.ts web/src/main.ts web/src/render.ts
+git commit -m "feat(backfill): retroactively resync PR summaries to the structured format; drop the 14-day window"
+```
+
+---
+
+### Task 6: Full-suite verification
+
+**Files:** none (verification only)
+
+**Interfaces:** none.
+
+- [ ] **Step 1: Run the full test suite**
+
+Run: `npm test`
+Expected: PASS — all suites green, including `test/prSummary.test.ts`,
+`test/summarize.test.ts`, `test/render.mywork.test.ts`, `test/backfill.test.ts`, and
+every pre-existing suite untouched by this plan.
+
+- [ ] **Step 2: Full typecheck**
+
+Run: `npm run typecheck`
+Expected: no errors across `src/`, `web/`, and `shared/`.
+
+- [ ] **Step 3: Build the web bundle**
+
+Run: `npm run build:web`
+Expected: builds cleanly (catches any import/path issue Vitest's module resolution
+might not).
+
+- [ ] **Step 4: Manual sanity check (optional but recommended)**
+
+Run: `npm run dev`, sign in, open My Work. Confirm: To-do renders above Previous
+activity; a To-do card shows an "updated" time and a wrapped (not truncated) title;
+a Previous-activity card with an old (pre-change) summary still renders as plain
+prose (no crash); as admin, click "Sync GitHub" and confirm the flash message shows
+a "summaries updated" count.