From fe12859ba215b2c86aa6c34368e9204d22546761 Mon Sep 17 00:00:00 2001
From: Bryan Van Deusen <bryan.vandeusen@fabledsword.com>
Date: Mon, 20 Jul 2026 20:10:45 -0400
Subject: [PATCH] ops: wait for the database on startup (no crash-loop on a
 slow DB)
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New thoughtsync.dbwait polls the DB (SELECT 1) up to 60×1s before startup,
logging each attempt, so a briefly slow/unready database no longer crash-
loops the container. Wired as `python -m thoughtsync.dbwait &&` ahead of
`alembic upgrade head` in the image CMD and the dev compose command; exits
non-zero after the window so a restart policy can take over. Prod compose
gains restart: unless-stopped as the complementary piece.

Co-Authored-By: Claude Opus 4.8 (1M context) <noreply@anthropic.com>
Claude-Session: https://claude.ai/code/session_01FRgehjoz7Yv8LkUfADxACm
---
 Dockerfile                |  7 ++---
 docker-compose.dev.yml    |  3 ++-
 docker-compose.yml        |  1 +
 src/thoughtsync/dbwait.py | 54 +++++++++++++++++++++++++++++++++++++++
 4 files changed, 61 insertions(+), 4 deletions(-)
 create mode 100644 src/thoughtsync/dbwait.py

diff --git a/Dockerfile b/Dockerfile
index f76fa36..625bc85 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -30,6 +30,7 @@ ARG BUILD_VERSION=dev
 ENV APP_VERSION=$BUILD_VERSION
 
 EXPOSE 5000
-# Run migrations, then serve. Family convention (rule 82): schema is built by real
-# migrations, never metadata.create_all.
-CMD ["sh", "-c", "alembic upgrade head && hypercorn 'thoughtsync.app:create_app()' --bind 0.0.0.0:5000 --keep-alive 600"]
+# Wait for the database, run migrations, then serve. The DB wait keeps a briefly
+# slow/unready database from crash-looping the container. Family convention
+# (rule 82): schema is built by real migrations, never metadata.create_all.
+CMD ["sh", "-c", "python -m thoughtsync.dbwait && alembic upgrade head && hypercorn 'thoughtsync.app:create_app()' --bind 0.0.0.0:5000 --keep-alive 600"]
diff --git a/docker-compose.dev.yml b/docker-compose.dev.yml
index f2673b9..669a328 100644
--- a/docker-compose.dev.yml
+++ b/docker-compose.dev.yml
@@ -40,9 +40,10 @@ services:
       - thoughtsync-dev-data:/var/thoughtsync
     ports:
       - "5000:5000"
-    # Install deps, run migrations, then serve with live reload on the mounted src.
+    # Install deps, wait for the DB, run migrations, then serve with live reload.
     command: >
       sh -c "pip install --quiet -e . &&
+             python -m thoughtsync.dbwait &&
              alembic upgrade head &&
              hypercorn 'thoughtsync.app:create_app()' --bind 0.0.0.0:5000 --reload"
 
diff --git a/docker-compose.yml b/docker-compose.yml
index 28f14dc..56de89c 100644
--- a/docker-compose.yml
+++ b/docker-compose.yml
@@ -19,6 +19,7 @@ services:
 
   app:
     build: .
+    restart: unless-stopped
     depends_on:
       db:
         condition: service_healthy
diff --git a/src/thoughtsync/dbwait.py b/src/thoughtsync/dbwait.py
new file mode 100644
index 0000000..59ef140
--- /dev/null
+++ b/src/thoughtsync/dbwait.py
@@ -0,0 +1,54 @@
+from __future__ import annotations
+
+import asyncio
+import sys
+
+from sqlalchemy import text
+from sqlalchemy.ext.asyncio import create_async_engine
+
+from .config import Config
+
+ATTEMPTS = 60
+DELAY_SECONDS = 1.0
+
+
+async def _probe(url: str) -> None:
+    engine = create_async_engine(url)
+    try:
+        async with engine.connect() as conn:
+            await conn.execute(text("SELECT 1"))
+    finally:
+        await engine.dispose()
+
+
+async def wait_for_db(attempts: int = ATTEMPTS, delay: float = DELAY_SECONDS) -> bool:
+    """Poll the database until it accepts a connection, up to `attempts` tries.
+
+    Startup runs `alembic upgrade head` as the container's first DB touch, so a
+    database that is a moment slow to accept connections would otherwise crash the
+    container. This gives it a short window to come up, verifying once per `delay`
+    seconds, instead of failing on the first missed connection.
+    """
+    url = Config.DATABASE_URL
+    for attempt in range(1, attempts + 1):
+        try:
+            await _probe(url)
+            print(f"[dbwait] database ready (attempt {attempt}/{attempts})", flush=True)
+            return True
+        except Exception as exc:
+            print(
+                f"[dbwait] not ready (attempt {attempt}/{attempts}): {exc.__class__.__name__}: {exc}",
+                flush=True,
+            )
+            if attempt < attempts:
+                await asyncio.sleep(delay)
+    print(f"[dbwait] database unreachable after {attempts} attempts; giving up", flush=True)
+    return False
+
+
+def main() -> int:
+    return 0 if asyncio.run(wait_for_db()) else 1
+
+
+if __name__ == "__main__":
+    sys.exit(main())