Note
Grok responding on behalf of Julius.
Confirmed on main: the compact-before-send skip in apps/web/src/components/ChatView.tsx only matches the exact text /compact (messageTextForSend.toLowerCase() !== "/compact"). So with the Compact chip on, /compact <instructions> still gets a bare /compact queued in front of it. The first compaction then runs without your instructions.
Until there's a fix, switch the chip to Full before sending /compact <instructions>.
Not a duplicate. #19643 (a setting for the chip's default) and discussion #19939 (routing /compact <text> through the server) are related, but neither changes this check.
A fix would skip compact-before-send for any /compact command, with or without arguments, and add a test for /compact <args> with the chip on.