Merge: /auth/bootstrap seed-user fix

app/auth/router.py

@@ -105,35 +105,51 @@ async def bootstrap(
     request: BootstrapRequest,
     conn: duckdb.DuckDBPyConnection = Depends(_get_db),
 ):
-    """Create the first admin user. Only works when no users exist.
+    """Bootstrap the first admin account.
 
-    This endpoint allows an AI agent to bootstrap a fresh instance
-    without needing docker exec or SSH. It automatically deactivates
-    after the first user is created.
+    Allowed when no user has a password_hash yet. This covers:
+    (a) No users exist at all.
+    (b) Only seed users (created by SEED_ADMIN_EMAIL at startup) exist, which
+        have no password and cannot log in — bootstrap lets the operator
+        activate them with a password.
+
+    If a user with the given email already exists (e.g. as a seed), this
+    endpoint sets its password_hash (or clears it, if no password was supplied —
+    useful for OAuth-only flows) and promotes it to admin.
+
+    Deactivates as soon as any user has a password_hash.
     """
     repo = UserRepository(conn)
     existing = repo.list_all()
-    if existing:
+
+    # Bootstrap is locked once anyone has a password set.
+    users_with_password = [u for u in existing if u.get("password_hash")]
+    if users_with_password:
         raise HTTPException(
             status_code=403,
-            detail=f"Bootstrap disabled — {len(existing)} users already exist. Use /auth/token to login.",
+            detail=f"Bootstrap disabled — {len(users_with_password)} user(s) already have passwords set. Use /auth/password/login.",
         )
 
-    user_id = str(uuid.uuid4())
-    password_hash = None
-    if request.password:
-        password_hash = PasswordHasher().hash(request.password)
+    password_hash = PasswordHasher().hash(request.password) if request.password else None
 
-    repo.create(
-        id=user_id,
-        email=request.email,
-        name=request.name or request.email.split("@")[0],
-        role="admin",
-        password_hash=password_hash,
-    )
+    # If a matching user already exists (e.g. seed), update it; else create fresh.
+    existing_user = next((u for u in existing if u.get("email") == request.email), None)
+    if existing_user:
+        user_id = existing_user["id"]
+        repo.update(id=user_id, password_hash=password_hash, role="admin")
+        _audit(user_id, "bootstrap_activated_seed")
+    else:
+        user_id = str(uuid.uuid4())
+        repo.create(
+            id=user_id,
+            email=request.email,
+            name=request.name or request.email.split("@")[0],
+            role="admin",
+            password_hash=password_hash,
+        )
+        _audit(user_id, "bootstrap_completed")
 
     token = create_access_token(user_id=user_id, email=request.email, role="admin")
-    _audit(user_id, "bootstrap_completed")
     return TokenResponse(
         access_token=token,
         user_id=user_id,

tests/test_bootstrap.py

@@ -17,7 +17,7 @@ def fresh_client(tmp_path, monkeypatch):
 
 @pytest.fixture
 def seeded_client(tmp_path, monkeypatch):
-    """Client with one existing user."""
+    """Client with one existing seed user (no password_hash — like SEED_ADMIN_EMAIL seeding)."""
     monkeypatch.setenv("DATA_DIR", str(tmp_path))
     monkeypatch.setenv("JWT_SECRET_KEY", "test-secret-32chars-minimum!!!!!")
     from app.main import create_app
@@ -29,6 +29,27 @@ def seeded_client(tmp_path, monkeypatch):
     return TestClient(create_app())
 
 
+@pytest.fixture
+def password_user_client(tmp_path, monkeypatch):
+    """Client with a user who already has a password set — bootstrap must be disabled."""
+    from argon2 import PasswordHasher
+    monkeypatch.setenv("DATA_DIR", str(tmp_path))
+    monkeypatch.setenv("JWT_SECRET_KEY", "test-secret-32chars-minimum!!!!!")
+    from app.main import create_app
+    from src.db import get_system_db
+    from src.repositories.users import UserRepository
+    conn = get_system_db()
+    UserRepository(conn).create(
+        id="existing",
+        email="existing@test.com",
+        name="E",
+        role="admin",
+        password_hash=PasswordHasher().hash("pre-existing-pass"),
+    )
+    conn.close()
+    return TestClient(create_app())
+
+
 class TestBootstrap:
     def test_bootstrap_on_empty_db(self, fresh_client):
         """First call creates admin and returns token."""
@@ -55,13 +76,30 @@ class TestBootstrap:
         resp2 = fresh_client.get("/api/health")
         assert resp2.status_code == 200
 
-    def test_bootstrap_disabled_when_users_exist(self, seeded_client):
-        """Bootstrap fails with 403 when users already exist."""
+    def test_bootstrap_activates_seed_user(self, seeded_client):
+        """Bootstrap activates a password-less seed user (SEED_ADMIN_EMAIL scenario)."""
         resp = seeded_client.post("/auth/bootstrap", json={
+            "email": "existing@test.com",
+            "password": "newpass123",
+        })
+        assert resp.status_code == 200
+        assert resp.json()["role"] == "admin"
+
+        # Login now works
+        login = seeded_client.post("/auth/password/login", json={
+            "email": "existing@test.com",
+            "password": "newpass123",
+        })
+        assert login.status_code == 200
+
+    def test_bootstrap_disabled_when_password_user_exists(self, password_user_client):
+        """Bootstrap fails with 403 when any user already has a password set."""
+        resp = password_user_client.post("/auth/bootstrap", json={
             "email": "hacker@evil.com",
+            "password": "should-not-work",
         })
         assert resp.status_code == 403
-        assert "already exist" in resp.json()["detail"]
+        assert "already have passwords" in resp.json()["detail"]
 
     def test_bootstrap_then_login(self, fresh_client):
         """After bootstrap with password, /auth/token login works; without password it requires OAuth."""
@@ -90,11 +128,19 @@ class TestBootstrap:
         })
         assert resp.status_code == 401
 
-    def test_bootstrap_second_call_fails(self, fresh_client):
-        """Second bootstrap call fails — endpoint self-deactivates."""
-        fresh_client.post("/auth/bootstrap", json={"email": "admin@test.com"})
+    def test_bootstrap_second_call_fails_once_password_set(self, fresh_client):
+        """Endpoint self-deactivates once any user has a password."""
+        # First call WITH password — locks bootstrap
+        fresh_client.post("/auth/bootstrap", json={
+            "email": "admin@test.com",
+            "password": "realpass123",
+        })
 
-        resp = fresh_client.post("/auth/bootstrap", json={"email": "second@test.com"})
+        # Any subsequent bootstrap attempt fails
+        resp = fresh_client.post("/auth/bootstrap", json={
+            "email": "second@test.com",
+            "password": "other-pass",
+        })
         assert resp.status_code == 403
 
     def test_full_agent_flow(self, fresh_client):