.gitignore

@@ -22,3 +22,8 @@ export/
 # NB: config/config.json IS committed on purpose — it's the v0.16 bootstrap
 # config and is secret-free (DB password comes from $STALWART_DB_PASSWORD via
 # the EnvironmentVariable secret type). Don't add it here.
+
+# Editor swap / backup files
+*.swp
+*.swo
+*~

LESSONS.md

@@ -0,0 +1,96 @@
+# tailwart — lessons learned
+
+Hard-won notes from bringing the mail edge up. Each entry is **symptom → cause →
+fix**, ordered roughly by how long it cost. Read this before re-debugging.
+
+## 1. Postgres startup race ate cert/setting writes
+
+**Symptom:** TLS certs (manual import *and* ACME) would validate but never
+persist — Stalwart kept serving its `rcgen` self-signed fallback. Logs showed
+`Failed to create tables: error connecting to server` on most boots.
+
+**Cause:** Stalwart shares the `ts-stalwart` sidecar's netns. Its `depends_on`
+only waited for the sidecar's *own* health (`/healthz` = "tailscaled up"), which
+flips green **before** the tailnet route to Postgres (`the-record-prod:5432`) is
+usable. Stalwart started into that gap, failed the DB connect, and any write in
+that window — including a freshly obtained cert — was silently lost.
+
+**Fix:** the sidecar healthcheck now also requires Postgres to be reachable
+(`nc -z … 5432`), so `depends_on: service_healthy` can't release Stalwart into
+the race. See `docker-compose.yml`. First clean boot after this: zero PG errors,
+4 live connections immediately.
+
+## 2. DNS-01 was blocked by a dead Spaceship API key
+
+**Symptom:** `Failed to set DNS RRSet: Unauthorized` on every record; no cert
+issued; no `_acme-challenge` TXT ever set.
+
+**Cause:** the cert design is ACME **DNS-01** via the **Spaceship** provider
+(bundled in caddy/lego). The stored API key was invalid (recovery debris from an
+earlier config attempt). Note `STALWART_ACME_PROVIDER` / `STALWART_ACME_TOKEN`
+in `.env` are **empty and not even passed through by compose** — the provider +
+secret are entered in the **admin UI** (stored in the DB), not via env.
+
+**Gotcha:** secret fields render **blank** in the Stalwart admin even when set
+(the S3 secret behaves identically). A blank field is *not* evidence it's unset.
+
+**Fix / how to verify a key directly (egresses the box's WAN IP, same as
+Stalwart):**
+```bash
+curl -i 'https://spaceship.dev/api/v1/dns/records/<domain>?take=5&skip=0' \
+  -H 'X-Api-Key: KEY' -H 'X-Api-Secret: SECRET'
+# 401 application.unauthorized = bad key/secret or IP-restricted
+# 200 = good
+```
+A fresh Spaceship key fixed it.
+
+## 3. Stalwart's auto-ban vs PROXY protocol (the "8080 mystery")
+
+**Symptom:** the edge box could relay mail fine but could **not** reach
+Stalwart's `:8080` admin — connections accept then immediately close. Looked like
+"tagged devices rejected, user phone works."
+
+**Cause:** Stalwart's fail2ban checks the **proxied client IP** (from the PROXY
+header) on the mail listeners, but the **raw connection IP** on the non-proxied
+admin listener. A banned edge-box IP therefore still relays mail (ban checked
+against the header IP) while direct `→:8080` is dropped (checked against the box
+IP). Malformed probing of the mail ports **re-arms** the ban.
+
+**Fix:** add `100.64.0.0/10` (and the box's WAN IP, which appears as the proxied
+client when you hit the box's own public hostname) to the fail2ban allow-list.
+Bans are in-memory — a Stalwart restart flushes them. **Don't rapid-poll the mail
+ports** to test.
+
+## 4. The wildcard request *required* DNS-01 (why HTTP-01 was a dead end)
+
+With "Additional Hostnames" left empty, Stalwart requests a **wildcard**
+(`*.<domain>`). Wildcards can **only** be issued via DNS-01 — HTTP-01 literally
+cannot satisfy them. We burned time on an HTTP-01 + Caddy-challenge-forwarding
+detour before realizing DNS-01 was the intended (and only viable) path. One
+wildcard cert then covers `mail`, `mta-sts`, `autoconfig`, `autodiscover`, etc.
+
+## 5. `:443` web endpoints need SNI pass-through, not L7 proxy
+
+MTA-STS / autoconfig / autodiscover serve over **:443**. You cannot L7
+`reverse_proxy` them through Caddy, because the **CAA** record pins issuance to
+Stalwart's ACME account — Caddy can't get its own cert for those names. Stalwart
+holds the wildcard, so the edge **passes TLS through** by SNI. See
+`caddy/README.md` → "The HTTP side". Needed `tcp:443` added to the
+`reverse-proxy → stalwart` ACL grant.
+
+## 6. The sidecar is ephemeral — never hardcode its tailnet IP
+
+`ts-stalwart` runs with `?ephemeral=true`, so its tailnet IP **changes on
+re-registration** (an ACL re-sync did this mid-debug: `100.112.26.122 →
+100.79.87.80`). Everything must use the MagicDNS name
+`stalwart.tail7b1641.ts.net`. A hardcoded IP will mysteriously go
+`Network is unreachable`.
+
+## 7. Don't trust crt.sh for rate-limit checks
+
+crt.sh was flaky/empty all session. To gauge Let's Encrypt's weekly
+duplicate-cert limit, use **certspotter** instead:
+`https://api.certspotter.com/v1/issuances?domain=<d>&include_subdomains=true`.
+Also: LE limits are dimensioned — **failed validations** are hourly (5/hr/host,
+the one a retry storm trips), **issued duplicates** are weekly (5/wk). A renewal
+task hammering every 10 min trips the hourly one; consolidate to a single task.

acl-snippet.hujson

@@ -12,10 +12,13 @@
 
 // 3) grants — the edge proxy (tag:reverse-proxy) reaches the mailbox ports.
 //    8080 is the JMAP/admin HTTP tier (fronted by the main L7 Caddy).
+//    443 is Stalwart's HTTPS web listener; the edge L4-proxies the public
+//    mta-sts/autoconfig/autodiscover SNIs to it (Stalwart terminates TLS with
+//    its wildcard cert). PROXY protocol v2, same as the mail ports.
 {
   "src": ["tag:reverse-proxy"],
   "dst": ["tag:stalwart"],
-  "ip":  ["tcp:25", "tcp:465", "tcp:587", "tcp:143", "tcp:993", "tcp:8080"],
+  "ip":  ["tcp:25", "tcp:465", "tcp:587", "tcp:143", "tcp:993", "tcp:443", "tcp:8080"],
 },
 
 // 4) admin console (not this file): assign tag:stalwart to the same OAuth

caddy/README.md

@@ -34,17 +34,43 @@ binary. To add plugins, append `&p=<url-encoded module path>` to
 can't read `.env`; this is the one spot the MagicDNS name is hardcoded — same
 trade-off as pgAdmin's `servers.json`.)
 
-## The HTTP side (JMAP / autoconfig / admin) is separate
+## The HTTP side (MTA-STS / autoconfig / autodiscover) — `:443` SNI fan-out
 
-That part *is* ordinary layer 7. Don't put it here if this box already runs the
-main Caddy on :443 — you'll collide. Instead add a vhost to the existing Caddy:
+Stalwart publishes DNS that points public HTTPS names at this edge:
+`mta-sts.`, `autoconfig.`, `autodiscover.<domain>`. They serve the MTA-STS
+policy and mail-client autoconfig over **:443** — so the edge has to handle
+`:443` too, which is where a naive setup collides with a box that already runs a
+web Caddy.
+
+The fix is **not** an L7 `reverse_proxy` (terminate at Caddy). You can't: the
+domain's **CAA** record pins issuance to Stalwart's ACME account
+(`accounturi=…`), so Caddy can't obtain its own cert for `*.<domain>`. Stalwart
+already holds the wildcard. So we **pass TLS through** to it.
+
+The `web` server in `caddy.json` owns `:443` and fans out by SNI:
+
+- `mta-sts` / `autoconfig` / `autodiscover.<domain>` → `stalwart:443`
+  (pass-through; Stalwart terminates with its wildcard cert — **no** proxy
+  protocol on `:443`, unlike the mail ports).
+- every other SNI → `127.0.0.1:8443`, the box's own web Caddy.
+
+For that fallback to exist, move the web Caddy's HTTPS off `:443`:
 
 ```caddyfile
-mail.infinidim.net {
-    reverse_proxy stalwart.tail7b1641.ts.net:8080
+{
+    https_port 8443    # web vhosts now listen here; the L4 :443 forwards to them
 }
+
+your-web-site.example { reverse_proxy … }
 ```
 
+HTTP→HTTPS redirects still resolve to `:443` correctly. A **mail-only** edge (no
+web vhosts on the box) omits the `web` server entirely — keep just the mail
+ports above.
+
+> Note: `tag:reverse-proxy → tag:stalwart` must also grant **`tcp:443`** in the
+> Tailscale ACL (see `../acl-snippet.hujson`), on top of the mail ports.
+
 ## Prerequisites on the host running this
 
 - Joined to the tailnet, tagged `tag:reverse-proxy` (so the ACL lets it reach

caddy/caddy.json

@@ -45,6 +45,30 @@
             "proxy_protocol": "v2",
             "upstreams": [{ "dial": ["stalwart.tail7b1641.ts.net:993"] }]
           }]}]
+        },
+        "web": {
+          "//": "SNI fan-out on the public :443. Stalwart's HTTPS web endpoints",
+          "//2": "(MTA-STS policy, autoconfig, autodiscover) pass through to Stalwart,",
+          "//3": "which terminates TLS with its wildcard cert — NO proxy_protocol here,",
+          "//4": "unlike the mail ports above. Every other SNI falls to the box's own",
+          "//5": "web Caddy on :8443 (set `https_port 8443` there). A mail-only standalone",
+          "//6": "edge omits this server. See README — 'The HTTP side'.",
+          "listen": [":443"],
+          "routes": [
+            {
+              "match": [{ "tls": { "sni": ["mta-sts.infinidim.net", "autoconfig.infinidim.net", "autodiscover.infinidim.net"] } }],
+              "handle": [{
+                "handler": "proxy",
+                "upstreams": [{ "dial": ["stalwart.tail7b1641.ts.net:443"] }]
+              }]
+            },
+            {
+              "handle": [{
+                "handler": "proxy",
+                "upstreams": [{ "dial": ["127.0.0.1:8443"] }]
+              }]
+            }
+          ]
         }
       }
     }

docker-compose.yml

@@ -31,9 +31,14 @@ services:
       - NET_ADMIN
       - NET_RAW
     healthcheck:
-      test: ["CMD", "wget", "-qO-", "http://127.0.0.1:9002/healthz"]
+      # Healthy only when BOTH the tailnet link is up AND Postgres is reachable
+      # over it. The stalwart service gates on this (depends_on: service_healthy),
+      # so it can no longer start into the race where it tries the DB before the
+      # tailnet route exists — which logged "Failed to create tables" and dropped
+      # in-flight cert/setting writes (e.g. lost the ACME cert on 2026-06-10).
+      test: ["CMD-SHELL", "wget -qO- http://127.0.0.1:9002/healthz && nc -z -w3 ${DB_MAGIC_NAME}.${TS_TAILNET} 5432"]
       interval: 10s
-      timeout: 5s
+      timeout: 8s
       retries: 6
       start_period: 30s
     restart: unless-stopped