My Work: To-do first, structured PR-summary cards, retroactive resync

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).

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 = /\*\*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 };
+}

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);
@@ -186,17 +181,28 @@ 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,
  pr_number: parsed.pr.number,
  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 };
 }

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}` },
  ],
  });

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).

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 = /\*\*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 };
+}

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);
@@ -186,17 +181,28 @@ 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,
  pr_number: parsed.pr.number,
  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 };
 }

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}` },
  ],
  });

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).

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 = /\*\*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 };
+}

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);
@@ -186,17 +181,28 @@ 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,
  pr_number: parsed.pr.number,
  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 };
 }

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}` },
  ],
  });

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).

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 = /\*\*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 };
+}

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);
@@ -186,17 +181,28 @@ 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,
  pr_number: parsed.pr.number,
  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 };
 }

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}` },
  ],
  });

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).

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 = /\*\*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 };
+}

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);
@@ -186,17 +181,28 @@ 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,
  pr_number: parsed.pr.number,
  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 };
 }

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}` },
  ],
  });

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).

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 = /\*\*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 };
+}

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);
@@ -186,17 +181,28 @@ 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,
  pr_number: parsed.pr.number,
  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 };
 }

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}` },
  ],
  });

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).

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 = /\*\*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 };
+}

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);
@@ -186,17 +181,28 @@ 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,
  pr_number: parsed.pr.number,
  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 };
 }

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}` },
  ],
  });

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).

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 = /\*\*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 };
+}

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);
@@ -186,17 +181,28 @@ 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,
  pr_number: parsed.pr.number,
  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 };
 }

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}` },
  ],
  });