1 files changed, 90 insertions, 0 deletions
diff --git a/docs/superpowers/plans/2026-08-03-post-0.1.0-usability-closed.md b/docs/superpowers/plans/2026-08-03-post-0.1.0-usability-closed.md
index b9eb8cf..a0337f1 100644
--- a/docs/superpowers/plans/2026-08-03-post-0.1.0-usability-closed.md
+++ b/docs/superpowers/plans/2026-08-03-post-0.1.0-usability-closed.md
@@ -8112,3 +8112,93 @@ separate Release configure with the option OFF reported a clean `0.27.0`. The
 suite is 37 of 38, the one failure being item 136 on an unrelated path.
 
 **Size: XS**, as sized.
+
+## 166. Mail you send to your own other account loses `inbox`
+
+**Observed (agent, 2026-08-25, while setting up msmtp.)** Four test messages
+were sent to one of the user's own accounts, one from each configured sending
+account. All four were delivered and indexed. The two sent from accounts whose
+Sent folder is fetched locally arrived in the recipient account's Inbox
+**without the `inbox` tag**, so they were absent from that account's Inbox view.
+The two sent from an account whose Sent folder is not fetched kept `inbox`
+normally.
+
+**Cause: established, and it is the `post-new` hook, not this binary.**
+`strip_inbox_from_sent()` in `assets/hooks/post-new` removes `inbox` from any
+message matching a configured sent folder's PATH. Its docstring states the
+assumption exactly: "the provenance is the file's own path: a message inside a
+configured sent folder is one this system sent, and `inbox` was never true of
+it."
+
+That holds for one file. It fails for one MESSAGE, because **notmuch
+deduplicates by Message-ID and a message can have several files**. When the
+sender and the recipient are both the user's own accounts, mbsync fetches two
+copies: the sender's Sent copy and the recipient's Inbox copy. notmuch stores
+them as ONE message with two filenames. The carve-out's query matches via the
+Sent filename and strips `inbox` from the message object, which is the same
+object the recipient's Inbox copy belongs to.
+
+Measured: one message, two paths, one in the sender account's sent folder and
+one in the recipient account's `Inbox/cur`.
+
+The assumption is not merely incomplete, it is false in this case: the message
+was genuinely sent AND genuinely received. There is no single right answer for
+"was `inbox` ever true of this message", because it was true of one file and
+false of another.
+
+**Approach.** Not settled, and the choice matters more than the code:
+
+1. **Strip only when EVERY file is in a sent folder.** Closest to the existing
+   intent, and it makes the predicate match the docstring's claim. A
+   self-addressed message keeps `inbox`, which is right: it did arrive.
+2. **Strip only when the message has exactly one file.** Simpler to express,
+   but it silently stops protecting any sent message that happens to be
+   duplicated for an unrelated reason.
+3. **Leave it.** Self-addressed mail is rare outside testing. The cost is that
+   it is invisible when it happens, and it looks exactly like the sync defect
+   item 104 turned out to be, which is how this was found.
+
+Option 1 is the one that makes the code true to what it already says it does.
+
+**Constraints.**
+
+- **The hook is this repo's**, `assets/hooks/post-new`, which the live
+  `database.hook_dir` symlinks to. It has its own suites beside it; run
+  `./test_post_new.py` and `./test_mailrules.py` from `assets/hooks/`.
+- The hook **tags real mail unattended, every ten minutes, on the user's live
+  index.** A predicate that is wrong in the other direction would strip `inbox`
+  from arriving mail, which is the failure mode PROTECTED_REMOVALS exists to
+  prevent. Test against a throwaway database first.
+- `notmuch tag` matching zero messages SUCCEEDS, so a log line saying the
+  carve-out ran is not evidence it matched anything. The count added for item
+  164 is what distinguishes them; use it.
+- Do not fix this by narrowing the query to exclude the recipient account. The
+  bug is in the per-file predicate, not in which folders are configured.
+
+**Fixed 2026-08-25, option 1**, the one the entry named: strip only when
+every file is in a sent folder.
+
+`sent_only()` in `assets/hooks/post-new` filters the matches and the tag is
+then applied per id. **It is a loop because no query can express it**, and both
+plausible query forms were measured against a real two-file message before the
+loop was written: `not path:"Inbox/**"` does NOT exclude the message, and
+`notmuch count --output=files` on a path query reports every file of every
+matching message rather than the files that matched. Both read as if they
+worked and are wrong for one reason, that a notmuch term is a predicate over a
+MESSAGE while the distinction here is between its FILES.
+
+The root comes from `database.mail_root`, not `database.path`, since this index
+is split and no message file sits under the index directory. The mutation
+putting `database.path` back passes every pre-existing test, because the
+ordinary fixture keeps the index inside the mail root and both keys return the
+same string; `setup_accounts(split_index=True)` is what catches it, and is the
+Python counterpart to `NotmuchFixture::splitIndex()`.
+
+Two mutations fail: `all` to `any` loses `inbox` on the self-addressed message,
+`mail_root` to `path` silently stops stripping anything.
+
+**Verified read-only against the live index**, tagging nothing: of 807 messages
+matching a sent path, 780 are still stripped and 27 are spared, every one of
+them two files with one in another account's Inbox. No arrival is affected.
+
+**Size: S.** Done.