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/components/routine-sections/editable-sections.tsx

@@ -27,6 +27,7 @@ import { nextCronFires, previewFirePolicies } from "../../lib/cron-fires";
 import { timeAgo } from "../../lib/timeAgo";
 import { EmptyState } from "../EmptyState";
 import { InlineEntitySelector } from "../InlineEntitySelector";
+import { DocumentAnnotationsCountChip, IssueDocumentAnnotations } from "../IssueDocumentAnnotations";
 import { AgentIcon } from "../AgentIconPicker";
 import { MarkdownEditor } from "../MarkdownEditor";
 import { ScheduleEditor, getScheduleCronValidation } from "../ScheduleEditor";
@@ -77,7 +78,11 @@ const signingModeDescriptions: Record<string, string> = {
 };
 const SIGNING_MODES_WITHOUT_REPLAY_WINDOW = new Set(["github_hmac", "none"]);
 
-export function OverviewSection() {
+export function OverviewSection({
+  defaultDescriptionAnnotationsOpen = false,
+}: {
+  defaultDescriptionAnnotationsOpen?: boolean;
+} = {}) {
   const ctx = useRoutineDetail();
   const {
     routine,
@@ -98,8 +103,11 @@ export function OverviewSection() {
     routineRuns,
     activity,
     saveRoutine,
+    saveConflict,
+    isSectionDirty,
     navigateToSection,
   } = ctx;
+  const [descriptionAnnotationsOpen, setDescriptionAnnotationsOpen] = useState(defaultDescriptionAnnotationsOpen);
 
   const activeTriggers = routine.triggers.length;
   const nextFire = useMemo(() => {
@@ -215,20 +223,63 @@ export function OverviewSection() {
       ) : null}
 
       {/* Instructions */}
-      <MarkdownEditor
-        ref={descriptionEditorRef}
-        value={editDraft.description}
-        onChange={(description) => setEditDraft((current) => ({ ...current, description }))}
-        placeholder="Add instructions..."
-        bordered={false}
-        contentClassName="min-h-[120px] text-[15px] leading-7"
-        mentions={mentionOptions}
-        onSubmit={() => {
-          if (!saveRoutine.isPending && editDraft.title.trim()) {
-            saveRoutine.mutate();
-          }
-        }}
-      />
+      <div className="space-y-2">
+        <div className="flex items-center justify-end">
+          {routine.descriptionDocument ? (
+            <DocumentAnnotationsCountChip
+              issueId={routine.id}
+              docKey="description"
+              target={{ kind: "routine", routineId: routine.id, documentKey: "description" }}
+              panelOpen={descriptionAnnotationsOpen}
+              onToggle={() => setDescriptionAnnotationsOpen((open) => !open)}
+            />
+          ) : null}
+        </div>
+        {routine.descriptionDocument ? (
+          <IssueDocumentAnnotations
+            issueId={routine.id}
+            doc={routine.descriptionDocument}
+            target={{ kind: "routine", routineId: routine.id, documentKey: "description" }}
+            bodyMarkdown={editDraft.description}
+            draftDirty={isSectionDirty("overview") || saveRoutine.isPending}
+            draftConflicted={saveConflict}
+            historicalPreview={false}
+            locationHash={typeof window === "undefined" ? "" : window.location.hash}
+            panelOpen={descriptionAnnotationsOpen}
+            onPanelOpenChange={setDescriptionAnnotationsOpen}
+          >
+            <MarkdownEditor
+              ref={descriptionEditorRef}
+              value={editDraft.description}
+              onChange={(description) => setEditDraft((current) => ({ ...current, description }))}
+              placeholder="Add instructions..."
+              bordered={false}
+              contentClassName="min-h-[120px] text-[15px] leading-7"
+              mentions={mentionOptions}
+              onSubmit={() => {
+                if (!saveRoutine.isPending && editDraft.title.trim()) {
+                  saveRoutine.mutate();
+                }
+              }}
+            />
+          </IssueDocumentAnnotations>
+        ) : (
+          <MarkdownEditor
+            ref={descriptionEditorRef}
+            value={editDraft.description}
+            onChange={(description) => setEditDraft((current) => ({ ...current, description }))}
+            placeholder="Add instructions..."
+            bordered={false}
+            contentClassName="min-h-[120px] text-[15px] leading-7"
+            mentions={mentionOptions}
+            onSubmit={() => {
+              if (!saveRoutine.isPending && editDraft.title.trim()) {
+                saveRoutine.mutate();
+              }
+            }}
+          />
+        )}
+      </div>
 
       {/* Variables peek */}
       <div className="space-y-3">