"You should know" builtin plugin never analyzes in Claude Desktop sessions (Windows, CLI 2.1.295 embedded)

The builtin cc-plugin-you-should-know is enabled and works in the terminal CLI (it offered a note on 2026-10-13,
CLI 2.1.296), but it has never produced a note in Claude Desktop sessions on the same machine and config dir.

Evidence:

• Desktop launches the embedded CLI (`...\Claude\claude-code\2.1.295\...\claude.exe --output-format stream-json

--input-format stream-json ...). The session starts with no surface (session.start: raised (surface none, not
interactive)) and the Desktop surface only arrives later via session.attach`.

• In turn.step the plugin returns early unless session.surfaces() is non-empty AND contains "terminal" or a

surface the plugin itself already rendered AbovePrompt on. Debug log from a Desktop session (2.1.288):
$.session.surfaces (cc-plugin-you-should-know): nothing attached draws; [].

• The plugin store writes askedTurn for every session that reaches the analysis step and only prunes past 32

sessions. After many long Desktop sessions (dozens of multi-tool turns) the store still holds a single entry,
from one terminal session. So the analysis step is never reached under Desktop.

Expected: the plugin analyzes Desktop sessions (its own surface table lists desktop: true) and shows the note in
the Desktop prompt area, or at least writes it to the store.
Environment: Windows 11, Claude Desktop 2.37337.1.0 (MSIX), embedded CLI 2.1.295; terminal CLI 2.1.301.