Add Helpdesk outbox worker validation

docs/helpdesk_outbox_worker_validation.md

@@ -0,0 +1,60 @@
+# Helpdesk Outbox Worker Validation
+
+Use `validate_helpdesk_outbox_worker.py` to verify that controlled Helpdesk
+activity creates the expected `event_outbox_events` rows and that
+`redmine_outbox_worker.py` can enrich those rows without processing them.
+
+## Run
+
+```sh
+./validate_helpdesk_outbox_worker.py
+```
+
+The script first runs the full Helpdesk/redMCP smoke path:
+
+- sends an inbound email to Mailpit for `fud-helpdesk`
+- triggers Helpdesk mail import on the LAN Redmine host
+- verifies `issueWithHelpdesk()` metadata
+- verifies normal `updateIssue()` does not send customer mail
+- verifies explicit Helpdesk reply delivery through Mailpit
+- closes the controlled Helpdesk issue unless `--keep-open` is passed
+
+It then queries `event_outbox_events` for the created issue and dry-runs
+`redmine_outbox_worker.enrich_event()` against those exact rows.
+
+## Expected Checks
+
+The validator fails if any of these are missing:
+
+- `helpdesk_ticket.created`
+- `helpdesk_ticket.updated`
+- `journal_message.created`
+- `journal.created`
+- `issue.updated`
+- derived worker document types: `event`, `ticket`, and `message`
+
+It also confirms the new rows have not been locked or marked processed, and
+that worker documents do not expose raw `bcc_address` data.
+
+## Configuration
+
+Defaults match the LAN test setup:
+
+- Redmine: `http://192.168.50.170`
+- SSH: `reddev@192.168.50.170`, key `/tmp/reddev`
+- remote Redmine path: `/usr/share/redmine`
+- Mailpit: `192.168.1.105`, SMTP `1025`, HTTP `8025`
+- API key source: `REDMINE_API_KEY`, `REDMNINE_API_KEY`, or `redMCP/.env`
+
+Useful options:
+
+```sh
+./validate_helpdesk_outbox_worker.py --skip-preflight
+./validate_helpdesk_outbox_worker.py --keep-open
+```
+
+## Expected Output
+
+The final summary should include the created issue id, Helpdesk ticket ids,
+journal message ids, event row ids/types, and derived document type counts.
+The worker mode should report dry-run enrichment only.

docs/helpdesk_smoke_test.md

@@ -48,3 +48,7 @@ Smoke test passed.
 
 Closed smoke-test tickets are intentionally retained in `fud-helpdesk` as audit
 evidence. Their subjects start with `[redMCP-smoke ...]`.
+
+For outbox and worker coverage, run `./validate_helpdesk_outbox_worker.py`.
+That script reuses this same live smoke path, then checks the matching
+`event_outbox_events` rows and dry-runs worker enrichment.

docs/redmineup_local_fork_changelog.md

@@ -27,11 +27,38 @@ environment. Before risky edits, archive the current plugin directories in
     manual browser testing.
   - Helpdesk mail import, Helpdesk metadata lookup, default non-email updates,
     and explicit outbound Helpdesk replies are live-smoke-tested through redMCP.
-  - Helpdesk outbox/worker validation is still pending.
+  - Helpdesk outbox/worker validation now has a repeatable live script.
 - Next meaningful milestone:
-  - Validate `redmine_outbox_worker.py` end to end against controlled Helpdesk
-    activity, document the derived JSONL shape, then choose the external index
-    target.
+  - Run `validate_helpdesk_outbox_worker.py` after outbox or worker changes,
+    then choose the external index target and durable processing policy.
+
+## 2026-04-25 - Helpdesk Outbox Worker Validation
+
+- Touched areas:
+  - Helpdesk test tooling
+  - External outbox worker validation docs
+- Purpose:
+  - Make Helpdesk outbox coverage repeatable after database refreshes and
+    worker changes.
+  - Validate worker enrichment against a real Mailpit-imported Helpdesk ticket
+    without claiming rows or marking them processed.
+- Behavior checked:
+  - Controlled Helpdesk import produces `helpdesk_ticket.created`,
+    `helpdesk_ticket.updated`, `journal_message.created`, `journal.created`,
+    and `issue.updated` rows.
+  - Worker dry-run enrichment emits `event`, `ticket`, and `message` documents.
+  - Derived message documents expose `has_bcc_address` but do not expose raw
+    `bcc_address`.
+- LAN test result:
+  - `./validate_helpdesk_outbox_worker.py` passed against `fud-helpdesk` and
+    `fud-nohelpdesk`.
+  - Latest documented passing run created and closed controlled Helpdesk issue
+    `#39873`.
+  - Observed outbox rows: 1 `helpdesk_ticket.created`, 3
+    `helpdesk_ticket.updated`, 1 `journal_message.created`, 3
+    `journal.created`, and 2 `issue.updated`.
+  - Worker dry-run enrichment produced 10 `event`, 6 `ticket`, and 2
+    `message` documents without claiming or marking rows processed.
 
 ## 2026-04-24 - Helpdesk/redMCP Smoke Validation
 

docs/test_instance_post_import.md

@@ -136,7 +136,20 @@ non-Helpdesk CRUD, confirms default updates do not send Helpdesk email, verifies
 explicit outbound Mailpit delivery, and closes the created test ticket. Details
 are in `docs/helpdesk_smoke_test.md`.
 
-## 8. Re-Run The Read-Only Validator
+## 8. Validate Helpdesk Outbox Worker Enrichment
+
+When Helpdesk/outbox behavior matters, run the repeatable live validator:
+
+```sh
+./validate_helpdesk_outbox_worker.py
+```
+
+This creates one controlled Helpdesk ticket through Mailpit, verifies redMCP
+Helpdesk behavior, checks the matching `event_outbox_events` rows, and dry-runs
+worker enrichment without claiming or marking rows processed. Details are in
+`docs/helpdesk_outbox_worker_validation.md`.
+
+## 9. Re-Run The Read-Only Validator
 
 Finish by running: