obsidian-vault/work/briefs/weekly/plan-2026-05-18.md

Weekly Plan — Week of 2026-05-18 (forward-looking: 2026-05-25 → 2026-05-29)

Note: Generated Sat 2026-05-23. The week of May 18 has already wrapped (Friday review = 2026-05-22). No weekly-review file exists at briefs/weekly/2026-05-22.md — plan built from DB snapshot only. Forward-looking content targets the upcoming work week (May 25 → May 29). AFK Wed May 27.

Top Priority: iOS Address onboarding conflicts with unified input and ship AI onboarding winner — confirmed by Alex's own comment on the TP-Threads task (2026-05-22): closing out the demo-tracker TP and starting Address onboarding as next O-N TP. Due 2026-06-05; in top_priority; subtasks already scoped for asset/UI work.

Quadrants

Quadrant	This Week	Notes
Project	65%	New O-N TP kickoff + closing demo-tracker PR; shortened week (AFK Wed) bumps from 60%
AOR	15%	UTI issues, CI failing tests, PR review backlog. Trimmed because week is 4 days
Career	15%	1:1 with Dominik Tue May 26 — Dominik NOT OOO (next AFK June 1–3). Boost vs baseline because 1:1 falls this week
Strategy	5%	O-N/O-L weekly, Apple Weekly. TD: Monthly pixels (Jonathan) — observe only

Shape

Sat 2026-05-23 / Sun 2026-05-24: Off — weekend.

Mon 2026-05-25: Close out, kick off

• iOS: Demo tracker blocking after chat in onboarding — final review pass on PR, address Alessandro's toggle question, hand off to reviewer
• PR: iOS: Demo tracker blocking after chat in onboarding — answer Alessandro (2026-05-22 comment about toggle remaining hidden until onboarding completes); reassign
• iOS Address onboarding conflicts with unified input and ship AI onboarding winner — async kick-off (in-person slots full per Alex's comment to Dominik); post kickoff note
• Address Universal Input (UTI) issues — wrap remaining UTI work before pivoting fully to new TP
• O-N Weekly Meeting (2026-05-25) — surface async-kickoff plan
• O-L Weekly Meeting (2026-05-25) — Dominik hosting; light agenda, no items required
• Set 1-Must for the day; post weekly TP

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 (Tue) — confirmed: Dominik not OOO until 2026-06-01
• Apple Weekly Team Meeting (2026-05-26)
• Persist 'You've got this' dialogue in non-focused state [0.5d] — start subtask of TP

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

• No work scheduled

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

• Address Bar Toggle Selection: Animated Assets [2-3d] — primary deep-work block
• Try Visiting a Site: Background [1d] — quick subtask if time

Fri 2026-05-29: Close loops + maintenance handoff

• Continue Address Toggle assets
• Weekly review (write it — last week's was missed)
• Handoff macOS App Maintenance to Tom (already assigned via May 29 cycle)
• Pre-1:1-next-cycle agenda items: add anything that surfaced

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

• iOS Address onboarding kickoff — async confirmation — assignee: Alex awaiting Dominik's reply on Alex's May 22 "kick-off slots taken — can we run async?" question — if no reply by Mon, ping Dominik so kickoff isn't delayed

• PR Check is failing on main — assignee: Alex due 2026-05-15 (8d overdue) — main-branch CI failure in active is a P1-style signal; not yet addressed. Diagnose Monday morning before deep work blocks

• Full Analysis — assignee: Alex due 2026-05-22 (1d overdue) — title alone is ambiguous (no project, no notes context surfaced in snapshot); open task and either action or re-scope. Surfacing because of recent due date

• Privacy Triage: Apple — iOS: Demo tracker blocking after chat in onboarding — assignee: Jake Abel delegated; due 2026-05-21 (2d overdue) — directly blocks closing TP. Nudge Jake on Monday if not done

AOR Quick Wins This Week

• Feature flag: warnBeforeQuit overdue 29 days — flag removal; standard cleanup, <1h

• Remove or re-evaluate Warn Before Quit pixels overdue 23 days — pair with the feature flag above; pixel cleanup

• Consider removing or reworking mac_malicious-site-protection_client-timeout overdue 304 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 (31d overdue) — active section, CI failing test; may overlap with the newer PR-Check task above

• Pinned tab opens link in background tab due 2026-05-01 (22d overdue) — Internal Product Feedback; pinned-tab regression

• Text selection in the address bar doesn't work as standard due 2026-05-01 (22d overdue) — Internal Product Feedback; UX regression

• Assertion Failure Pixel Anomaly - 2025/09/15 due 2025-09-17 (248d overdue) — planning section; revisit or close

• Review Overdue Tasks Summary - 22 Tasks (Jan 2026) due 2026-01-27 (116d overdue) — meta task about overdue management; ironic

(+ 2 aged items >180 days in backlog — not listed: Bug: Tab preview stuck around (403d), Duo login Grafana (304d))

On Radar

• TD: Monthly pixels for iOS and macOS — Jonathan Jackson revisited 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 following up on a macOS browser address-bar bug, reproducing on v1.190.0. Likely macOS AOR adjacency.

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 Project-Advisor doc draft because the 1:1 is the 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 to Dominik 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:

1. Project Advisor — "I've made no progress; want to commit to Part 1 of the Readiness doc this cycle. Sanity-check what 'good' looks like."
2. Primary AOR target — "Which AOR is realistic to pursue as primary by next review?"
3. Christie EP2/3 calibration — "Did she submit? Status unclear in my notes."
4. 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 returning to monthly-pixel approach (2026-05-23 comment) — touches Alex's instrumentation work; monitor, engage if Apple-team perspective is asked for

Carried Forward from Last Week

• iOS: Demo tracker blocking after chat in onboarding — Alex (DRI) → see TP / Monday in Shape — closing out PR, Privacy Triage delegated, 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 TP

• Address Universal Input (UTI) issues — Alex per Alex's May 22 comment: completing this before pivoting 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.

• 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 after WWDC AFK)

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Based on DB snapshot 2026-05-23 04:23 UTC + agent rhythms. Weekly-review for 2026-05-22 not found on disk — plan built from DB only. 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-2026-05-18.md.