Idempotent provisioning + auto re-invite of never-activated members

- provision_member reuses the stored LiteLLM key instead of minting a duplicate
  alias (LiteLLM 400s on member:<email>); fixes re-provisioning of existing members
- store_member preserves an existing slug when none is passed
- add welcome_sent_at + REINVITE_AFTER_DAYS; nightly sweep re-invites
  active members who never completed account setup, throttled to 3 days

app/main.py

@@ -20,6 +20,7 @@ import re
 import sqlite3
 import secrets
 import smtplib
+from datetime import datetime, timezone
 from email.mime.text import MIMEText
 from email.mime.multipart import MIMEMultipart
 
@@ -96,6 +97,12 @@ OC_PERSONAL_TOKEN = os.environ.get("OC_PERSONAL_TOKEN", "")
 # regardless of their $10/15/20 contribution. Governance decision (Loomio).
 MEMBER_BUDGET = float(os.environ.get("MEMBER_BUDGET", "15.0"))
 
+# Days to wait before re-sending the welcome/invite email to a member who was
+# provisioned but never completed account setup (inviteAccepted=False). The
+# nightly sweep re-invites such members, throttled by this interval so they
+# aren't emailed every single night.
+REINVITE_AFTER_DAYS = float(os.environ.get("REINVITE_AFTER_DAYS", "3"))
+
 # Models every member key/team may access.
 MEMBER_MODELS = ["deepseek-v4-1-flash", "gpt-oss-120b", "glm-5-3-flash"]
 
@@ -266,6 +273,10 @@ def get_db() -> sqlite3.Connection:
     # This is the flexible counter to the fixed $15/month allowance.
     if "balance" not in cols:
         conn.execute("ALTER TABLE members ADD COLUMN balance REAL")
+    # Migration: welcome_sent_at — timestamp of the last welcome/invite email,
+    # used to throttle re-invites of members who never activated.
+    if "welcome_sent_at" not in cols:
+        conn.execute("ALTER TABLE members ADD COLUMN welcome_sent_at TEXT")
     return conn
 
 
@@ -497,6 +508,13 @@ async def sync_loomio_memberships() -> None:
 
 def store_member(email: str, key_token: str, cloudron_user_id: str, slug: str = "") -> None:
     conn = get_db()
+    # Preserve an existing slug if the caller passed none — re-provisioning an
+    # already-provisioned member must not wipe their OC slug (the deactivation
+    # webhook maps slugs back to members).
+    if not slug:
+        row = conn.execute("SELECT slug FROM members WHERE email = ?", (email,)).fetchone()
+        if row and row[0]:
+            slug = row[0]
     conn.execute(
         "INSERT INTO members (email, key_token, cloudron_user_id, slug, active) "
         "VALUES (?, ?, ?, ?, 1) "
@@ -517,6 +535,33 @@ def get_member_key(email: str) -> str | None:
     return row[0] if row else None
 
 
+def get_stored_key(email: str) -> str | None:
+    """Return the stored LiteLLM key token regardless of active status.
+
+    Unlike get_member_key (which filters active=1), this returns the key even
+    for a lapsed member being reactivated, so provisioning can reuse it rather
+    than mint a duplicate alias (LiteLLM rejects a duplicate `member:<email>`
+    alias with 400).
+    """
+    conn = get_db()
+    row = conn.execute(
+        "SELECT key_token FROM members WHERE email = ?", (email,)
+    ).fetchone()
+    conn.close()
+    return (row[0] if row and row[0] else None)
+
+
+def touch_welcome_sent(email: str) -> None:
+    """Record that a welcome/invite email was just sent for this member."""
+    conn = get_db()
+    conn.execute(
+        "UPDATE members SET welcome_sent_at = datetime('now') WHERE email = ?",
+        (email,),
+    )
+    conn.commit()
+    conn.close()
+
+
 def get_member_by_slug(slug: str) -> dict | None:
     """Look up a member (email, key_token, cloudron_user_id) by their OC slug."""
     conn = get_db()
@@ -644,6 +689,25 @@ async def cloudron_get_invite_link(user_id: str) -> str:
         return r.json().get("inviteLink", "")
 
 
+async def cloudron_is_activated(user_id: str) -> bool:
+    """Return True if the user has completed account setup (inviteAccepted).
+
+    `inviteAccepted` flips true once the member clicks their setup link and
+    chooses a username/password. Until then they're provisioned but not able to
+    log in — the state we re-invite for.
+    """
+    async with httpx.AsyncClient() as client:
+        r = await client.get(
+            f"{CLOUDRON_API}/api/v1/users",
+            headers=cloudron_headers(),
+        )
+        r.raise_for_status()
+        for u in r.json().get("users", []):
+            if u.get("id") == user_id:
+                return bool(u.get("inviteAccepted"))
+    return False
+
+
 async def provision_member(email: str, name: str, slug: str = "") -> str:
     """Provision a member end-to-end and send our own welcome email.
 
@@ -652,21 +716,31 @@ async def provision_member(email: str, name: str, slug: str = "") -> str:
     stores the mapping, and sends our branded welcome email containing the
     Cloudron account-setup link (instead of Cloudron's default invite email).
 
-    Idempotent: if the member already exists, reuses the existing user/key.
+    Idempotent: if the member already has a stored LiteLLM key, reuse it rather
-    Returns the Cloudron user id.
+    than minting a new one (LiteLLM rejects a duplicate `member:<email>` alias
+    with 400 — the bug that previously made re-provisioning of existing members
+    fail). Re-sending this way also re-sends the welcome email, so it doubles
+    as the manual "re-invite" path.
     """
     user_id = await cloudron_create_user(email, name)
     await cloudron_set_group(user_id)
     await cloudron_set_active(user_id, True)
     balance = get_member_balance(email)
     team_id = await litellm_get_or_create_team(email, balance)
-    key_token = await litellm_create_key(email, balance, team_id)
+
+    # Reuse an existing key if we already have one (the sk- value is stored in
+    # our DB at creation time and is the authoritative token for this member's
+    # chat key). Only mint a fresh key when there is none.
+    key_token = get_stored_key(email)
+    if not key_token:
+        key_token = await litellm_create_key(email, balance, team_id)
     store_member(email, key_token, user_id, slug)
 
     # Send our own welcome email with the account-setup link (no OAuth step).
     setup_url = await cloudron_get_invite_link(user_id)
     subject, text, html = welcome_email(name, setup_url)
     send_email(email, subject, text, html)
+    touch_welcome_sent(email)
 
     # Subscribe to the member newsletter (single opt-in; members consented by joining).
     await listmonk_sync(email, subscribe=True)
@@ -1392,6 +1466,7 @@ async def reconcile_memberships() -> dict:
     """
     active = await fetch_members()
     active_emails = {m["email"] for m in active}
+    active_by_email = {m["email"]: m for m in active}
 
     # FAIL-SAFE: if the OC fetch returned nothing (token expired, OC outage,
     # or a query error), we must NOT deactivate everyone — that would be a
@@ -1434,6 +1509,48 @@ async def reconcile_memberships() -> dict:
             except Exception as e:
                 logger.warning("Sweep: failed to deactivate %s: %s", email, e)
 
+    # 2b. Re-invite never-activated members (provisioned but no account setup).
+    # A member who was provisioned (e.g. webhook fired while the OC token was
+    # missing the `email` scope, or the invite email went to spam) may sit
+    # active-but-unactivated indefinitely. Re-send their welcome email, but
+    # throttle by REINVITE_AFTER_DAYS so we don't spam them nightly.
+    reinvited_count = 0
+    conn = get_db()
+    reinvite_rows = conn.execute(
+        "SELECT email, cloudron_user_id, welcome_sent_at FROM members WHERE active = 1"
+    ).fetchall()
+    conn.close()
+    now = datetime.now(timezone.utc)
+    for email, user_id, sent_at in reinvite_rows:
+        if not user_id:
+            continue
+        # Skip if already activated.
+        try:
+            if await cloudron_is_activated(user_id):
+                continue
+        except Exception as e:
+            logger.warning("Sweep: activation check failed for %s: %s", email, e)
+            continue
+        # Throttle: only re-invite if the last send was > REINVITE_AFTER_DAYS ago.
+        if sent_at:
+            try:
+                last = datetime.fromisoformat(sent_at)
+                # stored as UTC naive (datetime('now') is UTC); attach tz
+                if last.tzinfo is None:
+                    last = last.replace(tzinfo=timezone.utc)
+                if (now - last).total_seconds() < REINVITE_AFTER_DAYS * 86400:
+                    continue
+            except Exception:
+                pass
+        # Re-send the welcome email (reuses the stored key — no duplicate alias).
+        try:
+            name = active_by_email.get(email, {}).get("name") or email.split("@")[0]
+            await provision_member(email, name, "")
+            reinvited_count += 1
+            logger.info("Sweep: re-invited %s (never activated)", email)
+        except Exception as e:
+            logger.warning("Sweep: failed to re-invite %s: %s", email, e)
+
     # 3. Sync Loomio.
     await sync_loomio_memberships()
 
@@ -1441,6 +1558,7 @@ async def reconcile_memberships() -> dict:
         "status": "reconciled",
         "provisioned": provisioned_count,
         "deactivated": deactivated_count,
+        "reinvited": reinvited_count,
     }