Weekly Plan — Week of 2026-06-01

Top Priority: iOS Address onboarding conflicts with unified input and ship AI onboarding winner — Ship Review milestone Fri 2026-06-05, three of four 0.5d/2d subtasks still open and overdue; WWDC AFK starts Mon Jun 8 so this MUST land before Friday.

Ship Review consolidation: All SR signals live here. The umbrella TP is in top_priority, modified today (not stale). Subtask state:

Ship AI onboarding winner (Treatment B) [0.5d] — PR #5145 CI 🔴, review ⏳. Fix the failing job first thing today.
Hide Free plan • Upgrade in onboarding [0.5d] — PR #5149 CI ✅, review ✅. Alessandro (2026-06-01 06:53) "let me know when the PR is ready for another look" — reply + merge. Reaction-only sign-off ≠ approval; rely on his actual comment.
Hide "stop chat" button [0.5d] — PR #5173 CI ✅, review ✅. Land today.
Persist 'You've got this' dialogue [2d] — due today, unstarted, biggest remaining slice. Protect Mon/Tue.
Try Visiting a Site: Background [1d] — due today, unstarted. Wed.
Ship Review: iOS Address onboarding… — Alex created/delegated, no reviewer comments yet → MONITORING. Verify scope + green build Thu before Fri.
[ON HOLD] iOS: Demo tracker blocking after chat in onboarding — modified 2026-06-01 00:31; on hold pending privacy triage from Jake Abel.

Quadrants

Quadrant	This Week	Notes
Project	75%	SR week — bumped from 60% target. Tradeoff: AOR/Career trimmed.
AOR	5%	Light: PRs already pending merge + 1 follow-up review. No new bug intake.
Career	10%	Dominik OOO all week (Jun 1–5), no 1:1 prep needed. Use slot for Project Advisor doc Part 1.
Strategy	10%	Windows AOT delivery plan reply Tue + WWDC AFK handoff Fri.

Shape

Mon (Jun 1): TP ramp + Monday ritual — process inbox, set 1-Must

Hide "stop chat" button [0.5d] — land
Hide Free plan • Upgrade [0.5d] — reply to Alessandro, merge
Ship AI onboarding winner [0.5d] — CI fix
Persist 'You've got this' dialogue [2d] — start
O-L Weekly Meeting

Tue (Jun 2): Continue TP deep work + Strategy reply

Persist 'You've got this' dialogue [2d] — continue
Apple Weekly Team Meeting
Desktop Browsers: Windows AOT delivery plan — substantive reply (Ivy starts work this week)

Wed (Jun 3): Finish Persist + start Try Visiting

Persist 'You've got this' dialogue [2d] — close
Try Visiting a Site: Background [1d] — start
O-N Weekly Meeting
Triage paired CI-failing-on-main tasks together (see AOR Quick Wins)

Thu (Jun 4): SR readiness + PR review queue

Try Visiting a Site: Background [1d] — finish
Verify Ship Review scope + green build
Clear GitHub review-requested queue (6 review-requests + 5 mentions, batch ~30 min)
PR: macOS Monterrey-only — push to merge (Diego's Jun 15 critical path)

Fri (Jun 5): Ship Review milestone + weekly review + AFK prep

Ship Review milestone
DRI <> Project Advisor async for Demo tracker — close
Draft Part 1 of Advisor Readiness doc (30 min) — career action
Weekly review + WWDC AFK handoff comment if Persist/Try Visiting slip into next week
Follow-up: Inline Text Images for TypingTextAnimation — REVIEWER, PR #4663 promote out of draft

Must-Not-Forget

Ship Review: iOS Address onboarding… — assignee: Alex due 2026-06-05 — Alex is DRI; SR scope must be verified Thu, no reviewer comments yet so no sign-off is in motion.
Persist 'You've got this' dialogue [2d] — assignee: Alex due 2026-06-01 — Largest unstarted TP subtask; the only one whose slip pushes SR into Alex's AFK window.
Privacy Triage: iOS Demo tracker blocking after chat — assignee: Jake Abel Jake's triage overdue since 2026-05-21 — directly blocks the on-hold Demo tracker subtask under this week's TP umbrella. Ping before Fri's SR.
PR: Make our macOS app Monterrey-only - 1-3d — assignee: Alex due 2026-05-27 (5d overdue) — On Diego's confirmed Jun 15 Monterey+ critical path; if Alex's PR doesn't land this week, Diego's release slips.
WWDC AFK Jun 8–12 — handoff prep — assignee: Alex Partly AFK starts next Mon (Jun 8). If Persist or Try Visiting slip, leave handoff comments on Fri. Otherwise no action — but easy to forget.

AOR Quick Wins This Week

Desktop Browser Feature Owner Survey [anonymous, 5-min timebox] overdue 6 days — 5-minute timebox per task title; clear in any gap.
Pinned tab opens link in background tab overdue 31 days — Stuck in inbox; triage to repro / quick fix or close as dup.
Text selection in the address bar doesn't work as standard overdue 31 days — Stuck in inbox; triage to repro / quick fix or close.

Sprint Backlog (pick 1–2 if time allows)

PR Check failing on main — testWhenTab…errorPageIsShownOnce due 2026-04-22 (40d overdue) — AOR: flake vs real regression. Sam S fixed a paired crashy macOS suite overnight; this one still open.
PR Check failing on main due 2026-05-15 (17d overdue) — Likely same family. Triage Wed alongside it — one fix may cover both.
Review Overdue Tasks Summary - 22 Tasks (Jan 2026) due 2026-01-27 (125d overdue) — Planning task; 30-min sweep to triage what's still alive vs close.

(+ 3 aged items >180 days in backlog — not listed: Tab preview stuck 412d, Duo Grafana 313d, Assertion Failure Pixel Anomaly 257d.)

On Radar

Drop macOS 11 Big Sur Support — Diego confirmed last Big Sur release Mon Jun 8; first Monterey+ merges next week. Alex's Monterrey-only PR feeds this — already a MNF.
SIGKILL inside MainViewController chrome bar reveal animation — Eduardo Pinto's defensive-weak-captures PR is up. AOR-adjacent (macOS UI lifecycle); monitor for review request.
CEF: Failing tests when 'setTabTitlesEarly' is enabled — Kris Wright zeroing in on root cause; worth a glance if test-helpers come up at Apple Weekly Tue.

Career Action This Week

Draft Part 1 of Advisor Readiness doc (30 min, Fri block).

Why this and not the others:

Project Advisor (Not started) is the highest-leverage EP3 lever, zero motion → picked.
Primary AOR discussion needs 1:1; Dominik OOO all week → defer to Jun 15+.
Calibration follow-up (Christie EP2/3) — defer; doesn't pair well with SR week.
Assessment visibility — no active O-N/O-L Assessment this week; Windows AOT reply (Strategy) already covers it.
1:1 career prep — Dominik OOO Jun 1–5, no 1:1. Skip.

On Radar / Participation Needed

Desktop Browsers: Windows - Produce delivery plan for Windows Browser AOT build Ivy + Mark replied Sat; Ivy picking it up Mon/Tue as her next TP. Alex's prior pushback ("don't get why the decision to spin off another project") is unanswered on substance. Silence reads as acquiescence — engage Tue with substantive reply (already in Shape).
Windows Browser: Re-enable isolated JS worlds Boli + Bulcsu discussing isolated worlds w/ new native script injection APIs (~couple days to a week). Apple/macOS-adjacent — monitor, engage only if pinged.

Carried Forward from Last Week

iOS Address onboarding conflicts with unified input and ship AI onboarding winner — assignee: Alex → see TP section above.
PR review queue — 11 items on GitHub — assignee: Alex (reviewer) 6 review-requests (privacy-configuration + apple-browsers) + 5 mentions. None overdue >5d as blocker; batch as one ~30-min Thu block.
DRI <> Project Advisor async for Demo tracker — assignee: Alex Open async with no clear next-action. Close this loop Friday before SR — either get the Project Advisor's call, or close with "moved to Ship Review thread" comment.
Privacy Triage: Apple - iOS: Demo tracker blocking after chat — assignee: Jake Abel → see Must-Not-Forget (10d overdue, blocks TP umbrella).
🤖 Check for dependabot PRs — assignee: Tom Strba Maintenance rotation item, due 2026-05-25 (7d overdue). Quick ping — confirm in-progress or pull back.
PR: C-S-S Fix site copy/cut/paste/text selection — assignee: delegated (unassigned in DB) Stale 76d, no GitHub PR match. Decide this week: chase, descope, or close.

Based on weekly-review absent (no Friday review on file for 2026-05-29) + DB state as of 2026-06-01 04:21 UTC (snapshot fresh)

Plan saved to /Users/admin/obsidian/work/briefs/weekly/plan-2026-06-01.md.

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