fix(bridge): stop replaying delivered output files on follow-up turns

[Mor-Li]

Problem

Every follow-up message within 5 minutes of a task that produced output files replays the entire outputs directory to the chat — say "thanks" after receiving report.pdf, and the bot sends report.pdf again (and repeats the oversized-file notice too).

Three pieces line up to cause it:

1. OutputsManager.prepareDir intentionally keeps files younger than the 5-minute retention window (RETENTION_MS),
2. scanOutputs is a stateless directory walk with no delivered-file filter,
3. sentPaths in OutputHandler.sendOutputFiles is method-local — it only dedupes within a single call, with zero memory across turns.

Fix

Bind delivery to deletion: once a file is sent, text-fallbacked, or accounted for via the oversized notice, unlink it so the next turn's scan doesn't see it. Files whose send threw are deliberately kept on disk (delivered stays false), so the follow-up turn retries them — the retention window still garbage-collects them eventually.

Tests (red/green verified)

tests/output-handler.test.ts gains a "resend prevention" suite; the two resend cases fail on the unfixed code:

× does not resend a delivered file on the next turn within the retention window
× does not repeat the oversized notice on the next turn
✓ keeps a file whose send threw, so the next turn can retry it   (semantics lock)

With the fix: file suite 9/9, full root suite 63 files / 665 tests green.

🤖 Generated with Claude Code

[floodsung]

This is the right delivery-bound direction and should supersede #336, but an additional failure-path probe shows files are still deleted when sendImageFile/sendLocalFile returns false. Please mark delivered only on a true send result or successful text fallback; retain files on false or throw, and cover both image/file false returns plus notice failure. Keeping open for the corrected head.

[Mor-Li]

@floodsung Thanks for the failure-path probe — fixed in ae0aa44. Delivery is now bound to proof of delivery rather than "didn't throw":

• Image sends: delivered takes the actual sendImageFile boolean; a false return retains the file for the next turn to retry.
• File sends: delivered on a true sendLocalFile result, or when the text fallback resolves; a false return with no applicable fallback (non-text or ≥30KB) retains the file.
• Oversized files: deletion is deferred until the coalesced notice actually reached the user (sendOversizedNotice now reports success); a failed notice keeps the files so the next turn re-raises it. Fallback-scan images (outside the outputs dir) are never deleted.

New tests cover all three probes: image false-return, file false-return without fallback, and notice failure + next-turn re-raise — plus one locking text-fallback delivery → deletion. All 13 output-handler tests pass.

🤖 Generated with Claude Code