diff --git a/.github/workflows/main.yml b/.github/workflows/main.yml
index d6e136f..192bade 100644
--- a/.github/workflows/main.yml
+++ b/.github/workflows/main.yml
@@ -49,6 +49,8 @@ jobs:
           uv sync --all-extras --all-groups --no-install-project
           uv run alembic upgrade head
           uv run pytest .
+          uv run alembic downgrade base
+          uv run pytest tests/migrations --override-ini=addopts=
         env:
           SERVICE_ENVIRONMENT: ci
           PYTHONDONTWRITEBYTECODE: 1
diff --git a/CLAUDE.md b/CLAUDE.md
index 8b2f4e8..7bcb684 100644
--- a/CLAUDE.md
+++ b/CLAUDE.md
@@ -46,6 +46,18 @@ on the host). Inside the container, raw commands look like `uv run pytest
 - `just test` cycles the DB (downgrade to `base`, upgrade to `head`) before
   pytest and tears the stack down before and after. Pass pytest args through,
   e.g. `just test tests/use_cases/test_create_chat.py -k race -x`.
+- `just test-migrations` runs the `pytest-alembic` suite (`tests/migrations/`):
+  single head, upgrade, per-revision up/down consistency, and
+  model-definitions-match-DDL — the last being `alembic check` as a test. That
+  directory is excluded from `just test` (`--ignore` in `addopts`, and from
+  `coverage`'s `omit`) because it cycles the schema out from under the
+  transaction-rollback fixture, so it needs the `--override-ini=addopts=` the
+  recipe passes. CI runs both.
+- Enum columns are native Postgres enums, and `alembic-postgresql-enum` is
+  imported by `migrations/env.py` for its autogenerate hooks — that is what
+  renders `CREATE TYPE` / `ALTER TYPE ... ADD VALUE` / `op.sync_enum_values`
+  instead of silently missing them. Add or rename an enum value and
+  `just migration` writes the type change for you.
 - `just migration "message"` takes a **single positional argument** — not a
   `-m` flag — quoted so a multi-word message survives as one token (the
   recipe shell-quotes it with `quote()` before handing it to `alembic
diff --git a/Justfile b/Justfile
index b02f2b0..34edc2e 100644
--- a/Justfile
+++ b/Justfile
@@ -12,6 +12,9 @@ test *args: down && down
 run:
     docker compose run --service-ports api sh -c "sleep 1 && uv run alembic upgrade head && uv run python -m app.api"
 
+test-migrations *args: down && down
+    docker compose run api sh -c "sleep 1 && uv run alembic downgrade base && uv run pytest tests/migrations --override-ini=addopts= {{ args }}"
+
 migration message: && down
     # `message` is a single named parameter, shell-quoted via quote() so a multi-word message
     # survives intact - a variadic *args parameter only ever joins tokens with spaces when
diff --git a/alembic.ini b/alembic.ini
index 455a1fa..9c8d7f5 100644
--- a/alembic.ini
+++ b/alembic.ini
@@ -11,6 +11,10 @@ file_template = %%(year)d-%%(month).2d-%%(day).2d_%%(slug)s
 # defaults to the current working directory.
 prepend_sys_path = .
 
+# separator for lists such as prepend_sys_path; without it Alembic falls back to
+# legacy splitting and warns, which filterwarnings = ["error"] turns into a failure.
+path_separator = os
+
 # timezone to use when rendering the date
 # within the migration file as well as the filename.
 # string value is passed to dateutil.tz.gettz()
diff --git a/app/database/tables.py b/app/database/tables.py
index 22983ca..27776d5 100644
--- a/app/database/tables.py
+++ b/app/database/tables.py
@@ -43,8 +43,7 @@ class ChatsTable(BigIntAuditBase):
     chat_type: orm.Mapped[ChatType] = orm.mapped_column(
         sa.Enum(
             ChatType,
-            native_enum=False,
-            create_constraint=True,
+            name="chattype",
             values_callable=lambda enum_cls: [member.value for member in enum_cls],
         )
     )
diff --git a/app/settings.py b/app/settings.py
index 3eb2d28..a5a771d 100644
--- a/app/settings.py
+++ b/app/settings.py
@@ -60,6 +60,11 @@ def ensure_jwt_secret_is_configured(self) -> None:
     def db_dsn_parsed(self) -> URL:
         return make_url(self.db_dsn)
 
+    @property
+    def sync_db_dsn_parsed(self) -> URL:
+        # Alembic drives psycopg2, not asyncpg.
+        return self.db_dsn_parsed.set(drivername="postgresql")
+
     @property
     def api_bootstrapper_config(self) -> LitestarConfig:
         return LitestarConfig(
diff --git a/migrations/env.py b/migrations/env.py
index c5fb8a6..86f1311 100644
--- a/migrations/env.py
+++ b/migrations/env.py
@@ -1,14 +1,16 @@
 from logging.config import fileConfig
 
+import alembic_postgresql_enum
 from alembic import context
-from sqlalchemy import URL, create_engine
+from sqlalchemy import create_engine
 
 from app.database.tables import METADATA
 from app.settings import settings
 
 
-def get_dsn() -> URL:
-    return settings.db_dsn_parsed.set(drivername="postgresql")
+# Imported for its side effect: registering the autogenerate hooks that render CREATE TYPE /
+# ALTER TYPE ... ADD VALUE for native Postgres enums.
+_ = alembic_postgresql_enum
 
 
 config = context.config
@@ -21,7 +23,7 @@ def get_dsn() -> URL:
 
 def run_migrations_offline() -> None:
     context.configure(
-        url=get_dsn(),
+        url=settings.sync_db_dsn_parsed,
         target_metadata=target_metadata,
         literal_binds=True,
         dialect_opts={"paramstyle": "named"},
@@ -31,7 +33,7 @@ def run_migrations_offline() -> None:
 
 
 def run_migrations_online() -> None:
-    connectable = create_engine(get_dsn())
+    connectable = create_engine(settings.sync_db_dsn_parsed)
     with connectable.connect() as connection:
         context.configure(connection=connection, target_metadata=target_metadata)
         with context.begin_transaction():
diff --git a/migrations/versions/2026-08-21_chat_type_native_enum.py b/migrations/versions/2026-08-21_chat_type_native_enum.py
new file mode 100644
index 0000000..db76f0d
--- /dev/null
+++ b/migrations/versions/2026-08-21_chat_type_native_enum.py
@@ -0,0 +1,50 @@
+"""chat type native enum.
+
+Revision ID: fa15d87677c3
+Revises: 1be68642e392
+Create Date: 2026-08-21 18:45:32.661982
+
+"""
+
+import sqlalchemy as sa
+from alembic import op
+
+
+# revision identifiers, used by Alembic.
+revision = "fa15d87677c3"
+down_revision = "1be68642e392"
+branch_labels = None
+depends_on = None
+
+
+def upgrade() -> None:
+    # ### commands auto generated by Alembic - please adjust! ###
+    sa.Enum("direct", "group", name="chattype").create(op.get_bind())
+    op.alter_column(
+        "chats",
+        "chat_type",
+        existing_type=sa.VARCHAR(length=6),
+        type_=sa.Enum("direct", "group", name="chattype"),
+        existing_nullable=False,
+        postgresql_using="chat_type::chattype",
+    )
+    op.drop_constraint(op.f("ck_chats_chattype"), "chats", type_="check")
+    # ### end Alembic commands ###
+
+
+def downgrade() -> None:
+    # ### commands auto generated by Alembic - please adjust! ###
+    op.create_check_constraint(
+        op.f("ck_chats_chattype"),
+        "chats",
+        "chat_type::text = ANY (ARRAY['direct'::character varying, 'group'::character varying]::text[])",
+    )
+    op.alter_column(
+        "chats",
+        "chat_type",
+        existing_type=sa.Enum("direct", "group", name="chattype"),
+        type_=sa.VARCHAR(length=6),
+        existing_nullable=False,
+    )
+    sa.Enum("direct", "group", name="chattype").drop(op.get_bind())
+    # ### end Alembic commands ###
diff --git a/migrations/versions/2026-08-21_messages.py b/migrations/versions/2026-08-21_messages.py
index 1470192..8a5b45a 100644
--- a/migrations/versions/2026-08-21_messages.py
+++ b/migrations/versions/2026-08-21_messages.py
@@ -38,13 +38,6 @@ def upgrade() -> None:
     op.create_index("ix_messages_chat_id_id", "messages", ["chat_id", "id"], unique=False)
     op.create_index(op.f("ix_messages_user_id"), "messages", ["user_id"], unique=False)
     # ### end Alembic commands ###
-    # NOTE: autogenerate also proposed `op.drop_constraint(op.f('ck_chats_chattype'), 'chats', type_='check')`
-    # here. That's a known Alembic false positive for `sa.Enum(native_enum=False, create_constraint=True)`
-    # columns: Postgres reflects the CHECK constraint body back as `chat_type::text = ANY (ARRAY[...])`,
-    # which never textually matches what Alembic renders from the model, so every autogenerate run
-    # "detects" this same constraint as removed even though nothing about `chats.chat_type` changed.
-    # Dropping it here would be unrelated to this migration's purpose (adding `messages`) and would
-    # silently remove enum validation from `chats.chat_type`, so it is intentionally omitted.
 
 
 def downgrade() -> None:
diff --git a/planning/changes/2026-08-21.03-native-enum-and-migration-tests.md b/planning/changes/2026-08-21.03-native-enum-and-migration-tests.md
new file mode 100644
index 0000000..f56bdd2
--- /dev/null
+++ b/planning/changes/2026-08-21.03-native-enum-and-migration-tests.md
@@ -0,0 +1,93 @@
+---
+summary: Converted chats.chat_type to a native Postgres enum with alembic-postgresql-enum and added a pytest-alembic suite, turning a permanently-dirty autogenerate into a green CI gate.
+---
+
+# Design: Native chat_type enum and a pytest-alembic migration suite
+
+## Summary
+
+`chats.chat_type` becomes a native Postgres enum instead of `VARCHAR` plus a
+CHECK constraint, `migrations/env.py` imports `alembic-postgresql-enum`, and
+`tests/migrations/` runs the four `pytest-alembic` built-ins. `alembic check` is
+clean for the first time, and migration health is now enforced by CI rather than
+by a comment asking readers to ignore a diff.
+
+## Motivation
+
+`sa.Enum(ChatType, native_enum=False, create_constraint=True)` produced a
+permanent autogenerate false positive: Postgres reflects the CHECK body back as
+`chat_type::text = ANY (ARRAY[...])`, which never textually matches what Alembic
+renders from the model, so every run proposed
+`op.drop_constraint('ck_chats_chattype')`. The cost was not cosmetic — it meant
+`alembic check` could never be a drift gate, and every `just migration` produced
+a spurious operation a human had to remember to delete. A note in
+`migrations/versions/2026-08-21_messages.py` documented that trap rather than
+removing it.
+
+The private `rchat` service already solved this: native `postgresql.ENUM`
+columns plus `alembic-postgresql-enum`, with `pytest-alembic` covering migration
+health in a separate CI job. This repo exists to show that stack working, so it
+should show that part too.
+
+## Design
+
+**Native enum.** `sa.Enum(ChatType, name="chattype", values_callable=...)` — the
+`values_callable` stays, so the type's labels remain the lowercase member values.
+`alembic-postgresql-enum`, imported for its side effect in `migrations/env.py`,
+autogenerated the whole conversion including the `USING` clause and a working
+downgrade:
+
+```python
+sa.Enum("direct", "group", name="chattype").create(op.get_bind())
+op.alter_column("chats", "chat_type", ..., postgresql_using="chat_type::chattype")
+op.drop_constraint(op.f("ck_chats_chattype"), "chats", type_="check")
+```
+
+Producing that by hand is exactly the work the library exists to remove, and it
+is what makes a future value addition a one-command change.
+
+**Migration tests.** `tests/migrations/test_migrations.py` imports
+`test_single_head_revision`, `test_upgrade`, `test_up_down_consistency` and
+`test_model_definitions_match_ddl` from `pytest_alembic.tests`. The last is
+`alembic check` as a test; the other three are coverage `just test` never had —
+it only ran `downgrade base && upgrade head`, which proves neither per-revision
+reversibility nor the absence of branched heads. A local `alembic_engine`
+fixture replaces pytest-alembic's default in-memory SQLite engine with the real
+Postgres DSN.
+
+The suite is excluded from the default run — `--ignore=tests/migrations` in
+`addopts`, `tests/migrations/*` in coverage's `omit` — because it cycles the
+schema out from under `db_session`'s transaction-rollback fixture. `just
+test-migrations` runs it with `--override-ini=addopts=`, and CI runs both.
+
+**Incidental.** `Settings.sync_db_dsn_parsed` now owns the
+`postgresql+asyncpg` → `postgresql` rewrite, which `migrations/env.py` and the
+`alembic_engine` fixture both need. `alembic.ini` gains `path_separator = os`:
+without it Alembic emits a `DeprecationWarning` that `filterwarnings = ["error"]`
+turns into a test failure.
+
+## Non-goals
+
+- Converting anything else. `chat_type` is the only enum column in the schema.
+- Suppressing the diff with an `include_object` filter in `env.py`. It would
+  have been two lines, but it hides a class of real diffs and keys on a
+  constraint name that the next enum column would not share.
+
+## Testing
+
+- `just test` — 109 passed, 100% coverage.
+- `just test-migrations` — 4 passed.
+- `just lint` — clean.
+- `alembic upgrade head && alembic check` — clean, where it previously reported
+  `remove_constraint ck_chats_chattype`. `alembic downgrade -1 && alembic
+  upgrade head` round-trips.
+
+## Risk
+
+- **Adding an enum value is now a migration.** That is the point — it was
+  previously an unenforced CHECK constraint edit — but it does mean a value
+  added to `ChatType` without running `just migration` fails
+  `test_model_definitions_match_ddl` rather than passing silently.
+- **The conversion is not free on a large table.** `ALTER COLUMN ... TYPE`
+  rewrites `chats`. It is cheap now, while the table is effectively empty, and
+  gets more expensive the longer it waits.
diff --git a/pyproject.toml b/pyproject.toml
index 1d6308d..e416bff 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -17,6 +17,7 @@ dependencies = [
     "db-retry",
     # database
     "alembic",
+    "alembic-postgresql-enum",
     "psycopg2",
     "sqlalchemy[asyncio]",
     "asyncpg",
@@ -34,6 +35,7 @@ dev = [
     "pytest-asyncio",
     "asgi_lifespan",
     "modern-di-pytest>=3,<4",
+    "pytest-alembic",
 ]
 lint = ["ruff", "ty", "eof-fixer"]
 
@@ -70,7 +72,7 @@ isort.no-lines-before = ["standard-library", "local-folder"]
 "migrations/*.py" = ["ERA001"]
 
 [tool.pytest.ini_options]
-addopts = "--cov=. --cov-report term-missing --cov-fail-under=100"
+addopts = "--cov=. --cov-report term-missing --cov-fail-under=100 --ignore=tests/migrations"
 asyncio_mode = "auto"
 asyncio_default_fixture_loop_scope = "function"
 filterwarnings = ["error"]
@@ -83,6 +85,9 @@ concurrency = ["thread", "greenlet"]
 disable_warnings = ["couldnt-parse"]
 omit = [
     "migrations/*",
+    # Excluded from the default pytest run (see addopts) because they cycle the schema; they
+    # run under `just test-migrations` instead, where coverage is off.
+    "tests/migrations/*",
     "app/api/__main__.py",
     # No __init__.py under planning/ (see the comment atop planning/index.py), so coverage's
     # package walk never reaches this file on its own - omit it explicitly rather than relying
diff --git a/tests/migrations/__init__.py b/tests/migrations/__init__.py
new file mode 100644
index 0000000..e69de29
diff --git a/tests/migrations/conftest.py b/tests/migrations/conftest.py
new file mode 100644
index 0000000..4f49702
--- /dev/null
+++ b/tests/migrations/conftest.py
@@ -0,0 +1,15 @@
+import typing
+
+import pytest
+from sqlalchemy import Engine, create_engine
+
+from app.settings import settings
+
+
+@pytest.fixture
+def alembic_engine() -> typing.Iterator[Engine]:
+    # Overrides pytest-alembic's default in-memory SQLite engine: these tests are only
+    # meaningful against the Postgres the migrations actually target.
+    engine: typing.Final = create_engine(settings.sync_db_dsn_parsed)
+    yield engine
+    engine.dispose()
diff --git a/tests/migrations/test_migrations.py b/tests/migrations/test_migrations.py
new file mode 100644
index 0000000..1b937f7
--- /dev/null
+++ b/tests/migrations/test_migrations.py
@@ -0,0 +1,12 @@
+from pytest_alembic.tests import (
+    test_model_definitions_match_ddl,
+    test_single_head_revision,
+    test_up_down_consistency,
+    test_upgrade,
+)
+
+
+_ = test_single_head_revision
+_ = test_upgrade
+_ = test_model_definitions_match_ddl
+_ = test_up_down_consistency
diff --git a/tests/test_settings.py b/tests/test_settings.py
index 87e3209..b424dbd 100644
--- a/tests/test_settings.py
+++ b/tests/test_settings.py
@@ -9,6 +9,12 @@ def test_db_dsn_parsed_exposes_driver() -> None:
     assert settings.db_dsn_parsed.database == "dbname"
 
 
+def test_sync_db_dsn_parsed_drops_the_async_driver() -> None:
+    settings = Settings(db_dsn="postgresql+asyncpg://user:pw@host/dbname")
+    assert settings.sync_db_dsn_parsed.drivername == "postgresql"
+    assert settings.sync_db_dsn_parsed.database == "dbname"
+
+
 def test_api_bootstrapper_config_carries_service_identity() -> None:
     settings = Settings(service_name="svc", service_version="9.9.9")
     config = settings.api_bootstrapper_config