Weekly Plan — Week of 2026-05-25

Note: No weekly-review file exists at briefs/weekly/2026-05-22.md. Plan rebuilt from DB snapshot 2026-05-25 02:01 UTC + last week's plan-2026-05-18.md. Shortened week: AFK Wed 2026-05-27 (holiday). 4 working days. Career advisor (Dominik) OOO check: clear through 2026-05-31; earliest AFK June 1–3 (LDX3). 1:1 Tuesday is GO. Quick Wins week: not announced.

Top Priority: iOS Address onboarding conflicts with unified input and ship AI onboarding winner — confirmed as next O-N TP (Alex's own May/22 note on TP-Threads bot task). Due 2026-06-05; in top_priority; subtasks already scoped for asset/UI work (Animated Assets [2-3d], Try Visiting a Site Background [1d], Persist 'You've got this' [0.5d]). Last week's TP (Demo tracker) is in final close-out (PR + Privacy Triage outstanding) — kept under Monday in Shape, not duplicated as TP.

Quadrants

Quadrant	This Week	Notes
Project	65%	New O-N TP kickoff + closing demo-tracker PR; shortened week (AFK Wed) bumps from 60% baseline
AOR	15%	2 PR-Check failures on main, UTI wrap, Sentry/CI maintenance, address-bar bug adjacency
Career	15%	1:1 with Dominik Tue May 26 — Dominik NOT OOO until June 1. Boost vs 5% baseline because 1:1 falls this week
Strategy	5%	O-N/O-L Weekly Mon, Apple Weekly Tue. TD: Monthly pixels (Jonathan) — observe only

Shape

Mon 2026-05-25: Close out + kick off (3 meetings stacked)

iOS: Demo tracker blocking after chat in onboarding — final review pass on PR; address Alessandro's toggle question; reassign reviewer
PR: iOS: Demo tracker blocking after chat in onboarding — due tomorrow; answer Alessandro's May/22 toggle-visibility question; hand off
iOS Address onboarding conflicts with unified input and ship AI onboarding winner — async kick-off post in TP comments (per Alex's May/22 note: in-person slots full)
Address Universal Input (UTI) issues — wrap remaining work before pivoting fully to new TP
Alex M next Top Priority (May/25) — bot-generated nudge; update due date or close once new TP declared
O-N Weekly Meeting — surface async-kickoff plan for new TP
O-L Weekly Meeting — Dominik hosting; light agenda
Set 1-Must for the day; declare weekly TP on team board

Tue 2026-05-26: 1:1 + meetings + light project work

Dominik :: Alex Regular 1:1 Agenda — add career items BEFORE meeting (see Career Action below)
1:1 with Dominik — confirmed: Dominik not OOO until 2026-06-01
Apple Weekly Team Meeting
Persist 'You've got this' dialogue in non-focused state [0.5d] — start subtask of new TP
Desktop Browser Feature Owner Survey — due today; 5-min timebox

Wed 2026-05-27: 🏖️ AFK (Alex M AFK May/27, holiday)

No work scheduled

Thu 2026-05-28: Deep work on new TP

Address Bar Toggle Selection: Animated Assets [2-3d] — primary deep-work block (due today)
Try Visiting a Site: Background [1d] — secondary subtask
Buffer for CI/AOR firefighting if PR-Check issues persist

Fri 2026-05-29: Close loops + retrospective

Continue Address Toggle assets if not done
Weekly review write-up (this week's + catch-up for May/22 if missing)
Handoff macOS App Maintenance to Tom (already assigned via May 29 cycle)
Pre-next-1:1 agenda items: capture anything that surfaced this week

Must-Not-Forget

PR: iOS: Demo tracker blocking after chat in onboarding — assignee: Alex due 2026-05-26 — Alessandro asked on 2026-05-22 whether the toggle should remain hidden until onboarding completes; Alex committed publicly to "review pass on Monday and assign to [reviewer]" — Alex IS the blocker. Action today.
Privacy Triage: Apple — iOS: Demo tracker blocking after chat in onboarding — assignee: Jake Abel delegated; due 2026-05-21 (4d overdue) — directly blocks closing last week's TP. Nudge Jake today if not done.
PR Check is failing on main — assignee: Alex due 2026-05-15 (10d overdue) — main-branch CI failure in inbox; P1-style signal. Diagnose Monday morning before deep-work blocks.
Full Analysis — assignee: Alex due 2026-05-22 (3d overdue) — title alone is ambiguous (no project, no notes context in snapshot); open and either action or re-scope.
Dominik :: Alex Regular 1:1 Agenda — assignee: Alex (preparer) due 2026-05-26 — needs career items added before Tue meeting (see Career Action).

AOR Quick Wins This Week

Feature flag: warnBeforeQuit overdue 31 days — flag removal; standard cleanup, <1h
Remove or re-evaluate Warn Before Quit pixels overdue 25 days — pair with the feature flag above; pixel cleanup
Consider removing or reworking mac_malicious-site-protection_client-timeout overdue 306 days — review whether still needed; quick scoping decision

Sprint Backlog (pick 1–2 if time allows)

PR Check is failing on main - testWhenTabWithConnectionLostErrorActivatedAndReloadFailsAgain_errorPageIsShownOnce due 2026-04-22 (33d overdue) — active section, CI failing test; may overlap with newer PR-Check task in MNF
Pinned tab opens link in background tab due 2026-05-01 (24d overdue) — Internal Product Feedback; pinned-tab regression
Text selection in the address bar doesn't work as standard due 2026-05-01 (24d overdue) — Internal Product Feedback; UX regression
Review Overdue Tasks Summary - 22 Tasks (Jan 2026) due 2026-01-27 (118d overdue) — meta task about overdue management

(+ 3 aged items >180 days in backlog — not listed individually: Bug: Tab preview stuck around (405d), Duo login Grafana (306d), Assertion Failure Pixel Anomaly (250d))

On Radar

TD: Monthly pixels for iOS and macOS — Jonathan Jackson returned to monthly-pixel approach on 2026-05-23. Touches pixel/instrumentation AOR Alex has worked in. Engage if Apple-team input solicited.
Discussion: shield in address bar overlapping with text — Zac confirmed reproduction on v1.190.0 (2026-05-23); macOS browser address-bar AOR adjacency; monitor for direct ask.

Career Action This Week

Add career discussion points to Dominik :: Alex Regular 1:1 Agenda before Tue 2026-05-26 (15 min)

Picked because 1:1 IS this week AND Dominik is NOT OOO (verified — next AFK is 2026-06-01). Skipped #1 (Project Advisor doc Part 1 draft) because the 1:1 is the more time-bounded action — raise Project Advisor as the primary agenda item in the 1:1 instead, same content, better leverage. Skipped Christie EP2/3 calibration ping — surface as a 1:1 question first ("did Christie submit?"), then act if needed. Skipped Assessment comment item — no current open O-N/O-L Assessment requires it this week.

Specific 1:1 agenda items to add (in priority order):

Project Advisor — "No progress since last cycle; want to commit to Part 1 of the Readiness doc this cycle. Sanity-check what 'good' looks like."
Primary AOR target — "Which AOR is realistic to pursue as primary by next review (~2026-08)?"
Christie EP2/3 calibration — "Did she submit? Status still unclear in my notes."
EP3 gap check — "Beyond what we discussed in Feb, what's the next gap to close?"

On Radar / Participation Needed

Tech Design: Monthly pixels for iOS and macOS Jonathan Jackson revisited monthly-pixel approach (2026-05-23 comment) — touches Alex's instrumentation work; monitor, engage if Apple-team perspective is explicitly asked for
shield in address bar overlapping with text Zac confirmed reproduction on v1.190.0 (2026-05-23); macOS address-bar AOR. Watch for any direct ask.

Carried Forward from Last Week

iOS: Demo tracker blocking after chat in onboarding — Alex (DRI) → see Mon in Shape — closing out PR, Privacy Triage delegated to Jake, Project-Advisor async open
DRI <> Project Advisor async for Demo tracker blocking after chat in onboarding — Alex async sign-off thread; verify status before closing the last TP
Address Universal Input (UTI) issues — Alex per Alex's May 22 note: completing this before pivoting fully to new TP — wrap on Monday
Alex Shurgin – HR — Alex HR-related task surfaced May 22; review for any time-sensitive action. ⚠️ HR content — handle privately, don't auto-summarize via connectors.
Postmortem: Security Triage AI: edit link + Postmortem: Security Triage: AI Agent use via likely external Discord service — Alex Security postmortems in inbox. Read, contribute if assigned an action; otherwise leave as observer. ⚠️ Security content — handle privately.
Xcode build speedup skill — Alex Personal tooling task; schedule in a gap day (likely post-WWDC AFK)
Alex M next Top Priority (May/25) — Alex bot-generated TP-threads nudge from May/24; close or update once new TP is declared today

Based on DB snapshot 2026-05-25 02:01 UTC + plan-2026-05-18.md (no weekly-review for 2026-05-22 on disk). DRI conflict check: none flagged. Career advisor (Dominik) OOO check: clear through 2026-05-31. Quick Wins week: not announced.

Saved to /Users/admin/obsidian/work/briefs/weekly/plan-2026-05-25.md.

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