fix: upstream deployed document-comment, routine-annotation, workspace & board-polling fixes (#8536)

## Thinking Path

> - Paperclip is the open source app people use to manage AI agents for
work
> - This change touches several already-shipped subsystems —
document-comment annotations, the selected-agent Conference Room chat
surface, routine description annotations, workspace-operation tracking,
and the board polling/inbox UI
> - A batch of incremental fixes and two small backend additions had
accumulated on a local mainline and were deployed to a live instance,
but never landed upstream — so each `origin/master` sync kept
re-diverging
> - Leaving them un-upstreamed means the same delta has to be re-merged
on every sync and risks being lost or silently reverted
> - This pull request rebases that delta cleanly on top of current
`origin/master` (preserving recent upstream work such as reusable
sandbox leases and the relation-list collapse controls) and brings it up
for review
> - The benefit is that mainline and the deployed instance converge, and
these fixes/additions get normal review + CI + Greptile coverage

## Linked Issues or Issue Description

No single GitHub issue tracks this; it is a bundle of bug fixes and two
small feature additions. Following the issue-template fields:

**Bug fixes (what was wrong → what this does):**
- Document comments rendered out of document order, didn't live-update
across clients, swallowed save failures, and lost the markdown text
selection on re-render. Now: doc-order sort, live updates, surfaced
save-failure state, stable selection across re-renders.
- The board polling hot path returned oversized payloads on every poll.
Now: an opt-in `summary` projection trims the heartbeat-run list
payload.
- Assorted UI fixes: sidebar nav peek/streamlining edge cases, markdown
file-viewer re-mount/line-height issues on iOS Safari, inbox badge/skill
deep-link tab selection, and `⌘.` work-mode cycling on iOS.

**Feature additions:**
- `workspace_operations.issue_id` — associate a workspace operation with
the issue that triggered it (new migration `0106`, schema, service,
shared type).
- Routine **description annotations** — comment threads on a routine's
description document, mirroring issue document annotations (new
migration `0107`, `routine_documents` schema, routes/service,
editable-sections UI).
- Selected-agent **Conference Room chat** surface wiring and live
issue-thread updates.

**Related PR:** #8229 (`feat(control-plane): add annotation and
workspace controls`, draft) covers overlapping
annotation/workspace-control territory — flagging it so a reviewer can
reconcile the two rather than double-merging.

## What Changed

- `feat(workspace)`: `workspace_operations.issue_id` migration +
schema/service/type; issue workspace property controls reconciled with
upstream's evolved "Service" row.
- `feat(routines)`: routine description annotations —
`routine_documents` schema, migration `0107`, routes/service,
`editable-sections` UI.
- `fix(document-comments)`: doc-order sort, live updates, save-failure
surfacing, stable markdown selection (+ storybook story, rerender test).
- `feat(chat)`: selected-agent Conference Room chat surface and live
issue-thread updates (`LiveUpdatesProvider`, `issue-chat-messages`,
interactions service).
- `perf(board)`: opt-in `summary` projection for the board
polling/heartbeat-run list payload, plus assorted sidebar / file-viewer
/ inbox / IssueProperties UI fixes.

Organized into 5 logical commits. Migrations are numbered incrementally
after upstream's latest (`0105`) — `0106` then `0107`, no journal
collision.

## Verification

- Built by 3-way merging the deployed delta onto current
`origin/master`; the only merge conflict (`IssueProperties.test.tsx`,
two adjacent test blocks) was resolved in favor of upstream's evolved
"green service link above the workspace row" layout, which matches the
merged component's rendered output.
- Confirmed recent upstream work is preserved post-merge: reusable
sandbox lease teardown (`#8513`), the IssueProperties relation-list
collapse controls, and the sidebar streamlined-nav default.
- Confirmed the net diff vs `origin/master` is exactly the intended
feature delta (65 files) and that overlapping server files (`issues.ts`,
`agents.ts`, `heartbeat.ts`) only add feature code without disturbing
upstream logic.
- This delta is already running on a live deployed instance.
- Full typecheck/test suite + Greptile to run in CI (see checklist).

## Risks

- Two new migrations (`0106`, `0107`). Both are additive (new table /
new nullable column) and ordered after upstream's `0105`; no data
backfill, low risk. If another migration-bearing PR merges first,
renumber before merge.
- Largest blast radius is in the merged overlapping UI/service files;
covered by the existing test suites for those files plus CI.
- Overlaps thematically with draft PR #8229 — reviewers should reconcile
rather than merge both blindly.

## Model Used

Claude Opus 4.8 (`claude-opus-4-8`), extended thinking, with tool use
(git, shell). Agentic coding workflow.

## Checklist

- [x] I have included a thinking path that traces from project context
to this change
- [x] I have specified the model used (with version and capability
details)
- [x] I have checked ROADMAP.md and confirmed this PR does not duplicate
planned core work
- [x] I have searched GitHub for duplicate or related PRs and linked
them above
- [x] I have either (a) linked existing issues with `Fixes: #` / `Closes
#` / `Refs #` OR (b) described the issue in-PR following the relevant
issue template
- [x] I have not referenced internal/instance-local Paperclip issues or
links (only public GitHub `#NNN` / `github.com/paperclipai/paperclip`
URLs)
- [ ] I have run tests locally and they pass
- [x] I have added or updated tests where applicable
- [x] I have updated relevant documentation to reflect my changes
- [x] I have considered and documented any risks above
- [ ] All Paperclip CI gates are green
- [ ] Greptile is 5/5 with no open P2s, recommendations, or follow-ups
- [ ] I will address all Greptile and reviewer comments before
requesting merge

---------

Co-authored-by: Paperclip <noreply@paperclip.ing>

ui/src/api/document-annotations.ts

@@ -11,27 +11,50 @@ import { api } from "./client";
 
 export type DocumentAnnotationListFilter = "open" | "resolved" | "all";
 
+export type DocumentAnnotationTarget =
+  | { kind: "issue"; issueId: string; documentKey: string }
+  | { kind: "routine"; routineId: string; documentKey: "description" };
+
+function issueTarget(issueId: string, documentKey: string): DocumentAnnotationTarget {
+  return { kind: "issue", issueId, documentKey };
+}
+
+function targetBasePath(target: DocumentAnnotationTarget) {
+  if (target.kind === "routine") {
+    return `/routines/${target.routineId}/description/annotations`;
+  }
+  return `/issues/${target.issueId}/documents/${encodeURIComponent(target.documentKey)}/annotations`;
+}
+
 export const documentAnnotationsApi = {
   list: (
     issueId: string,
     key: string,
     options: { status?: DocumentAnnotationListFilter; includeComments?: boolean } = {},
+  ) => documentAnnotationsApi.listForTarget(issueTarget(issueId, key), options),
+  listForTarget: (
+    target: DocumentAnnotationTarget,
+    options: { status?: DocumentAnnotationListFilter; includeComments?: boolean } = {},
   ) => {
     const params = new URLSearchParams();
     if (options.status) params.set("status", options.status);
     if (options.includeComments) params.set("includeComments", "true");
     const qs = params.toString();
     return api.get<DocumentAnnotationThreadWithComments[]>(
-      `/issues/${issueId}/documents/${encodeURIComponent(key)}/annotations${qs ? `?${qs}` : ""}`,
+      `${targetBasePath(target)}${qs ? `?${qs}` : ""}`,
     );
   },
   get: (issueId: string, key: string, threadId: string) =>
+    documentAnnotationsApi.getForTarget(issueTarget(issueId, key), threadId),
+  getForTarget: (target: DocumentAnnotationTarget, threadId: string) =>
     api.get<DocumentAnnotationThreadWithComments>(
-      `/issues/${issueId}/documents/${encodeURIComponent(key)}/annotations/${threadId}`,
+      `${targetBasePath(target)}/${threadId}`,
     ),
   create: (issueId: string, key: string, data: CreateDocumentAnnotationThreadRequest) =>
+    documentAnnotationsApi.createForTarget(issueTarget(issueId, key), data),
+  createForTarget: (target: DocumentAnnotationTarget, data: CreateDocumentAnnotationThreadRequest) =>
     api.post<DocumentAnnotationThreadWithComments>(
-      `/issues/${issueId}/documents/${encodeURIComponent(key)}/annotations`,
+      targetBasePath(target),
       data,
     ),
   addComment: (
@@ -39,9 +62,14 @@ export const documentAnnotationsApi = {
     key: string,
     threadId: string,
     data: CreateDocumentAnnotationCommentRequest,
+  ) => documentAnnotationsApi.addCommentForTarget(issueTarget(issueId, key), threadId, data),
+  addCommentForTarget: (
+    target: DocumentAnnotationTarget,
+    threadId: string,
+    data: CreateDocumentAnnotationCommentRequest,
   ) =>
     api.post<DocumentAnnotationComment>(
-      `/issues/${issueId}/documents/${encodeURIComponent(key)}/annotations/${threadId}/comments`,
+      `${targetBasePath(target)}/${threadId}/comments`,
       data,
     ),
   updateStatus: (
@@ -49,10 +77,15 @@ export const documentAnnotationsApi = {
     key: string,
     threadId: string,
     status: DocumentAnnotationThreadStatus,
+  ) => documentAnnotationsApi.updateStatusForTarget(issueTarget(issueId, key), threadId, status),
+  updateStatusForTarget: (
+    target: DocumentAnnotationTarget,
+    threadId: string,
+    status: DocumentAnnotationThreadStatus,
   ) => {
     const payload: UpdateDocumentAnnotationThreadRequest = { status };
     return api.patch<DocumentAnnotationThread>(
-      `/issues/${issueId}/documents/${encodeURIComponent(key)}/annotations/${threadId}`,
+      `${targetBasePath(target)}/${threadId}`,
       payload,
     );
   },