Weekly Plan — Week of 2026-05-31 (covers Mon 2026-06-01 → Fri 2026-06-05)

Context flag: No weekly-review file exists at /Users/admin/obsidian/work/briefs/weekly/2026-05-29.md (the entire weekly/ directory was missing — just created). Plan is built from DB snapshot only — carried-forward items inferred from current open tasks + PR state, not from a written review. Recommend running the weekly-review job for 2026-05-29 to establish a baseline.

Dominik OOO all week: Mon–Wed LDX3 ’26 (gid 1213155317359113), Thu–Fri Public Holiday (gid 1214633979837626). No 1:1 this week. Next available 1:1 window: ~Jun 9. Career time redirected to Project Advisor doc draft.

Top Priority: Ship the iOS Duck.ai onboarding launch — close out the 4 overdue Treatment B subtasks (Ship AI onboarding winner, Hide Free plan, Hide stop-chat button, Persist 'You've got this'). All 4 are in top_priority section, all DRI, three are 2–3 days overdue, and PR #5149 is already approved + green CI awaiting merge.

Quadrants

Quadrant	This Week	Notes
Project	65%	iOS Duck.ai onboarding ship-out + Address Bar Toggle assets (due 6/4) + Demo tracker blocking (due 6/5, currently ON HOLD — needs unblock check)
AOR	15%	Merge PR: Monterrey-only macOS (overdue 4d); investigate 2 CI-failing PR Check tasks; review Sentry SIGKILL PR (Eduardo) — AOR-secondary Crash Reporting
Career	15%	Dominik OOO → no 1:1. Substitute the saved 1:1-prep time with Project Advisor doc Part 1 (highest-leverage EP3 lever — currently "Not started")
Strategy	5%	Watch Fire Button simplify design thread; respond if direct ask. Light week.

Shape

Mon 6/1: TP push — close out overdue onboarding subtasks. 'Persist You've got this' due today.

Ship AI onboarding winner (Treatment B) [0.5d] — parent ship task
Hide Free plan • Upgrade in onboarding [0.5d] — PR #5149 approved + green, merge today
Persist 'You've got this' dialogue in non-focused state [2d] — due today
Try Visiting a Site: Background [1d] — also due today
O-L Weekly Meeting (1215106190309457)

Tue 6/2: TP — unblock and ship #5145 (CI red); chase review on #5173.

Hide "stop chat" button in the input box [0.5d] — PR #5173 ✅ CI, nudge reviewer
Investigate / fix CI on PR #5145
Apple Weekly Team Meeting (1215138977402987)

Wed 6/3: AOR + close remaining onboarding loose ends.

PR: Make our macOS app Monterrey-only - 1-3d — overdue 4d
PR Check is failing on main — investigate
O-N Weekly Meeting (1215156632997364)

Thu 6/4: Project deliverable + Career block.

Address Bar Toggle Selection: Animated Assets [2-3d] — due today
Career: Draft Part 1 of Advisor Readiness doc (30 min) — 1210386994396212

Fri 6/5: Demo tracker DRI deliverable + close-out + weekly review.

iOS Address onboarding conflicts with unified input and ship AI onboarding winner — due today
DRI <> Project Advisor async for Demo tracker blocking — verify ON HOLD on parent 1213551050320249; escalate if still blocked
Write weekly review for 2026-06-05

Must-Not-Forget

Hide Free plan • Upgrade in onboarding [0.5d] — assignee: Alex due 2026-05-28 (3d overdue) — PR #5149 has approval + green CI. Only blocker is hitting "merge". Do Mon AM.
Persist 'You've got this' dialogue in non-focused state [2d] — assignee: Alex due 2026-06-01 (Mon) — 2d sized. Must finish Mon/Tue to keep ship cluster on track.
Ship AI onboarding winner (Treatment B) [0.5d] — assignee: Alex due 2026-05-28 (3d overdue) — Parent / coordination task. Close once subtasks ship.
PR: Make our macOS app Monterrey-only - 1-3d — assignee: Alex due 2026-05-27 (4d overdue) — Diego confirmed Jun 8 is Big Sur's last; this is the Monterrey+ follow-up. Direct dependency on next release train.
iOS Address onboarding conflicts with unified input and ship AI onboarding winner — assignee: Alex due 2026-06-05 (Fri) — DRI task, downstream of Treatment B shipping. Protect Thu/Fri.

AOR Quick Wins This Week

Desktop Browser Feature Owner Survey [5 minute timebox] overdue 5 days — 5-min anonymous survey, just do it.
Review Overdue Tasks Summary - 22 Tasks (Jan 2026) overdue 124 days — quick triage pass.
Follow-up: add Inline Text Images to TypingTextAnimation overdue 3 days — PR #4663 already exists (draft, ✅ CI). Promote out of draft, request review.

Sprint Backlog (pick 1–2 if time allows)

PR Check failing - testWhenTabWithConnectionLostErrorActivated... due 2026-04-22 (39d overdue) — flaky/failing test in Apple CI.
PR Check is failing on main due 2026-05-15 (16d overdue) — investigate; may share root cause with above.
Text selection in the address bar doesn't work as standard due 2026-05-01 (30d overdue) — needs triage decision.
Pinned tab opens link in background tab due 2026-05-01 (30d overdue) — related to existing PR #4630.

(+ 3 aged items >180 days in backlog — not listed.)

On Radar

TD/PR: SIGKILL inside MainViewController chrome bar reveal animation (1215224247451374) — Eduardo Pinto put up defensive-weak-captures PR for a Sentry crash; touches Crash Reporting AOR-secondary. Skim; comment if pattern looks wrong.
Desktop Browsers: Design - Simplify Fire Button (1215239862935826) — Peter D + Mark aligning on timing; may produce Apple-team work later.
AOR: Desktop Browsers Operational Health (1214175673709906) — Elle flagged missing site_loading pixel on macOS — directly Alex's pixel-instrumentation territory.
Drop macOS 11 Big Sur Support (1210470859071348) — direct context for Alex's overdue Monterrey-only PR.

Career Action This Week

Picked: Draft Part 1 of Advisor Readiness doc (30 min) — Project Advisor goal is "Not started" per career-notes.md, highest-leverage EP3 lever. Skipped: (2) Primary AOR discussion — needs Dominik for 1:1, he's OOO. (3) Christie calibration follow-up — defer to next week with Dominik back. (4) Assessment comment — none active this week. (5) 1:1 prep — no 1:1 (Dominik OOO). Task: Readiness Self-Reflection for Potential Project Advisor. Block Thu afternoon.

On Radar / Participation Needed

Sorting in big HTML is 15sec compared to Vivaldi's 2 second Ivy suggested quick-win performance-test replication — touches macOS perf. Monitor.
[macOS] Reduce real WKWebView loads during unit tests Sam S exploring WKWebView CI crash fix; affects macOS test stability. Monitor.
CEF: Failing tests when 'setTabTitlesEarly' is enabled Kris W zeroing in on root cause; CEF-side. Monitor only.

Carried Forward from Last Week

Ship AI onboarding winner cluster (4 subtasks) — Alex → see TP section above.
PR: Make our macOS app Monterrey-only — Alex → see Must-Not-Forget above.
Address Bar Toggle Selection: Animated Assets — Alex Due 2026-06-04 (Thu) — protect Thu.
Try Visiting a Site: Background [1d] — Alex Due 2026-06-01 (Mon) — verify acceptance criteria before starting.
ON HOLD: iOS: Demo tracker blocking after chat in onboarding — Alex Due 2026-06-05; ON HOLD label. Check unblock by Wed; escalate if still blocked.
DRI <> Project Advisor async for Demo tracker blocking — Alex No due date, pairs with above. Resolve Fri.
PR #4663 (TypingTextAnimation Inline Images) — draft, ✅ CI; matches Asana 1214040804696193. Promote out of draft.
PR #4636 / #4634 / #4610 / #4559 — 4 executor PRs with 🔴 CI — diagnose during gap; do not let them rot.

Based on DB snapshot 2026-05-31 08:05 UTC (no weekly-review file present for 2026-05-29) + recurring-rhythms.md + career-notes.md. Saved to /Users/admin/obsidian/work/briefs/weekly/plan-2026-05-25.md.

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