davekilleen · davekilleen · Aug 7, 2026 · Aug 7, 2026
@@ -263,6 +263,8 @@ Check if any tasks were completed on phone since the last plan:
 Use: reminders_list_completed(list_name="Dex Today")
 ```
 
+**If the tool is unavailable or errors** (Apple Reminders sync is optional and may not be set up on this machine): skip this step silently — do not surface an error for a feature the user never enabled. Note: Reminders access never works when Claude Code runs inside the VS Code extension (macOS never shows the permission dialog to that process) — see the known limitation in `06-Resources/Dex_System/Calendar_Setup.md`. Do not advise reinstalling or reconfiguring; skip silently.
+
 For each completed item:
 - Match to a Dex task by title
 - Update task status via Work MCP: `update_task_status(task_title="...", status="d")`
@@ -432,6 +434,28 @@ Generate 3 recommended focus items based on:
 > 2. **Reply to Mike** — Commitment due today
 > 3. **Task X from Priority 1** — Keeps momentum on your shipped priority"
 
+**Task IDs are mandatory on focus items (completion sync depends on them):**
+
+Completion sync (Work MCP `update_task_status`, which updates every file the task
+appears in) only finds a line if that single line contains BOTH a `- [ ]` / `- [x]`
+checkbox AND the task's `^task-YYYYMMDD-XXX` anchor. A focus item written without the ID — or with the ID on
+a different line — is invisible to sync: ticking the task done in Tasks.md never
+updates the plan, and marking the plan item done never updates Tasks.md.
+
+So, for each recommended focus item:
+1. **If it maps to an existing Tasks.md task** (search by title/keywords), you MUST
+   write it in the plan as a `- [ ]` checkbox line with that task's `^task-YYYYMMDD-XXX`
+   anchor at the end of the same line. Never omit the ID, never put it on its own line.
+2. **If it's real work with no Tasks.md entry yet**, create the task first via Work MCP
+   `create_task`, then embed the returned task ID the same way.
+3. **Only if it isn't a task at all** (e.g. "protect the 2-4pm free block") may the line
+   omit an ID — and then it gets no checkbox either, so it can't masquerade as a
+   syncable task.
+
+Format notes that matter: use `- [ ]` (dash checkbox), not `1. [ ]` — numbered
+checkboxes do not contain the literal `- [ ]` string the sync matcher looks for, so
+they never sync even with an ID present.
+
 ### Meeting Prep (Enhanced)
 
 For each meeting, show:
@@ -455,6 +479,11 @@ Flag potential issues:
 
 **ALWAYS generate and save a new plan file.** Never skip generation because a plan from a previous day exists in the conversation or vault. Even if context from a prior plan is visible, today is a new day and requires its own plan. If a plan for today's date already exists, overwrite it (the user is requesting a refresh).
 
+**Filling in `{{^task-id}}` in Today's Focus:** replace it with the item's real
+`^task-YYYYMMDD-XXX` anchor per the Task IDs rule in Step 6 (mandatory whenever the
+item maps to a Tasks.md task — create the task first if needed). If the item is not a
+task at all, drop both the placeholder and the `- [ ]` checkbox for that line.
+
 Create `07-Archives/Plans/YYYY-MM-DD.md`:
 
 ```markdown
@@ -509,9 +538,9 @@ integrations_used: [calendar, tasks, people, work-intelligence]
 
 **If I only do three things today:**
 
-1. [ ] {{Focus item 1}} — {{Pillar}} *(supports Week Priority #X)*
-2. [ ] {{Focus item 2}} — {{Pillar}} *(supports Week Priority #Y)*
-3. [ ] {{Focus item 3}} — {{Pillar}}
+- [ ] {{Focus item 1}} — {{Pillar}} *(supports Week Priority #X)* {{^task-id}}
+- [ ] {{Focus item 2}} — {{Pillar}} *(supports Week Priority #Y)* {{^task-id}}
+- [ ] {{Focus item 3}} — {{Pillar}} {{^task-id}}
 
 ---
 
@@ -588,7 +617,7 @@ After generating the plan, push today's P0 and P1 focus tasks to Apple Reminders
 3. **Confirm silently:**
    > "📱 Pushed 3 focus tasks to iPhone Reminders (Dex Today)"
 
-**If Reminders MCP unavailable:** Skip silently.
+**If the tool is unavailable or errors:** Skip silently — do not surface an error for a feature the user never enabled. (This includes Claude Code running inside the VS Code extension, where macOS never grants Reminders access — see `06-Resources/Dex_System/Calendar_Setup.md`.)
 
 ---
 

@@ -110,7 +110,7 @@ Check for tasks added from phone during the day that weren't triaged in the morn
 Use: reminders_list_items(list_name="Dex Inbox")
 ```
 
-**If the tool is unavailable or errors** (Apple Reminders phone-capture is optional and may not be set up on this machine): skip this step silently — do not surface an error for a feature the user never enabled.
+**If the tool is unavailable or errors** (Apple Reminders phone-capture is optional and may not be set up on this machine): skip this step silently — do not surface an error for a feature the user never enabled. Note: Reminders access never works when Claude Code runs inside the VS Code extension (macOS never shows the permission dialog to that process) — see the known limitation in `06-Resources/Dex_System/Calendar_Setup.md`. Do not advise reinstalling or reconfiguring; skip silently.
 
 If items found:
 - Surface them: "📱 **Phone captures not yet triaged** (X items in Dex Inbox)"
@@ -131,6 +131,8 @@ Check if tasks were completed on phone since the morning plan:
 Use: reminders_list_completed(list_name="Dex Today")
 ```
 
+**If the tool is unavailable or errors** (Apple Reminders sync is optional and may not be set up on this machine): skip this step silently — do not surface an error for a feature the user never enabled. Note: Reminders access never works when Claude Code runs inside the VS Code extension (macOS never shows the permission dialog to that process) — see the known limitation in `06-Resources/Dex_System/Calendar_Setup.md`. Do not advise reinstalling or reconfiguring; skip silently.
+
 For each completed item:
 - Match to a Dex task by title
 - Update task status via Work MCP: `update_task_status(task_title="...", status="d")`
@@ -349,7 +351,25 @@ This only fires if the user has opted into analytics. No action needed if it ret
 
 ## Step 11: Evening Journal (If Enabled)
 
-If `journaling.evening: true`, prompt for evening reflection.
+Check `System/user-profile.yaml` → `journaling.evening`.
+
+**If `journaling.evening: true`, run the actual `/journal evening` flow** from
+`.claude/skills/journal/SKILL.md` — do not just mention reflection and move on, and do
+not substitute a single ad-hoc question. The real flow:
+
+1. Check if today's evening journal exists in `00-Inbox/Journals/`
+   - If yes: acknowledge it ("You already journaled this evening") and skip to Step 12
+   - If no: create it from the template
+2. Pull in this morning's journal intention (if one exists) for reflection
+3. Guide the user through the evening prompts conversationally — one question at a
+   time, per the journal skill's Prompting Style
+4. Save the entry, then continue the review
+
+Offer it plainly: "You have evening journaling enabled — want to do a quick reflection
+before we close the day?" If the user declines, skip without pushing back and continue
+to Step 12.
+
+**If `journaling.evening` is false or missing:** Skip this step silently.
 
 ---
 

@@ -464,7 +464,17 @@ Add a section to the review:
 
 After synthesis:
 1. Update Tasks.md with new priorities
-2. Archive completed items
+2. Clear completed tasks out of `03-Tasks/Tasks.md` — **remove whole task blocks, never
+   individual lines.** Tasks.md entries can span multiple lines: the `- [x]` checkbox
+   line plus its indented sub-lines (priority, due date, notes) and any continuation
+   paragraphs. A task's block runs from its checkbox line down to (but not including)
+   the next non-indented line — the next task's checkbox, a heading, or a blank line
+   followed by unindented content. When removing a completed task, remove that entire
+   block together so no orphaned sub-lines are left behind. Never do a per-line sweep
+   of `[x]` lines: that strands sub-lines, and it also removes completed sub-checkboxes
+   out from under tasks that are still open (only remove a block whose own top-level
+   checkbox is `[x]`). Before deleting anything, tell the user how many completed tasks
+   you're clearing and confirm.
 3. Update project pages with status changes
 4. Offer to run `/week-plan` for next week
 

@@ -51,6 +51,19 @@ The first time Cursor tries to read your calendar, macOS may show a popup: **"Cu
 
 ---
 
+## Known limitation: the VS Code extension can't use Apple Reminders
+
+macOS grants calendar and reminders access **per app** — it looks at which app is asking. When Dex runs through the **Claude Code extension inside VS Code** (rather than from a normal terminal window), macOS never shows the permission popup to that process at all, and access granted to Terminal does **not** carry over. The result: Apple Reminders features (phone capture via a "Dex Inbox" list, "Dex Today" sync) are simply unavailable in that setup — not misconfigured, unavailable. Reinstalling or redoing the setup steps will not change this.
+
+What to do instead:
+
+- **Run Dex from a standalone terminal window** (Terminal.app, or another terminal app launched on its own). The permission popup appears there, and access works after you click Allow.
+- **Or keep using the VS Code extension without Reminders features.** Dex skips them silently when access is unavailable — daily planning and reviews work normally without them.
+
+This was verified directly (August 2026): the same check succeeds from Terminal.app, and fails from both VS Code's built-in terminal and the extension's own process — even after access was granted in Terminal.app first.
+
+---
+
 ## Optional: Tell Dex which calendar is "work"
 
 If you have several calendars and want Dex to focus on one (e.g. your work calendar) for faster answers, you can set it in **System/user-profile.yaml** under a `calendar` section with `work_calendar: "your.email@example.com"` (use the exact name as it appears in the Calendar app). You can skip this—Dex will still show your events without it.

@@ -51,6 +51,19 @@ The first time Cursor tries to read your calendar, macOS may show a popup: **"Cu
 
 ---
 
+## Known limitation: the VS Code extension can't use Apple Reminders
+
+macOS grants calendar and reminders access **per app** — it looks at which app is asking. When Dex runs through the **Claude Code extension inside VS Code** (rather than from a normal terminal window), macOS never shows the permission popup to that process at all, and access granted to Terminal does **not** carry over. The result: Apple Reminders features (phone capture via a "Dex Inbox" list, "Dex Today" sync) are simply unavailable in that setup — not misconfigured, unavailable. Reinstalling or redoing the setup steps will not change this.
+
+What to do instead:
+
+- **Run Dex from a standalone terminal window** (Terminal.app, or another terminal app launched on its own). The permission popup appears there, and access works after you click Allow.
+- **Or keep using the VS Code extension without Reminders features.** Dex skips them silently when access is unavailable — daily planning and reviews work normally without them.
+
+This was verified directly (August 2026): the same check succeeds from Terminal.app, and fails from both VS Code's built-in terminal and the extension's own process — even after access was granted in Terminal.app first.
+
+---
+
 ## Optional: Tell Dex which calendar is "work"
 
 If you have several calendars and want Dex to focus on one (e.g. your work calendar) for faster answers, you can set it in **System/user-profile.yaml** under a `calendar` section with `work_calendar: "your.email@example.com"` (use the exact name as it appears in the Calendar app). You can skip this—Dex will still show your events without it.