diff --git a/packages/twenty-docker/twenty-app-dev/rootfs/etc/s6-overlay/scripts/init-db.sh b/packages/twenty-docker/twenty-app-dev/rootfs/etc/s6-overlay/scripts/init-db.sh
index 50ad6d2538..39339ed53e 100755
--- a/packages/twenty-docker/twenty-app-dev/rootfs/etc/s6-overlay/scripts/init-db.sh
+++ b/packages/twenty-docker/twenty-app-dev/rootfs/etc/s6-overlay/scripts/init-db.sh
@@ -34,25 +34,27 @@ has_schema=$(PGPASSWORD=twenty psql -h localhost -U twenty -d default -tAc \
   "SELECT EXISTS (SELECT 1 FROM information_schema.schemata WHERE schema_name = 'core')")
 
 if [ "$has_schema" = "f" ]; then
-  step_start "Running initial database setup"
-  NODE_OPTIONS="--max-old-space-size=1500" node ./dist/database/scripts/setup-db.js
+  step_start "Running initial database setup and migrations"
+  yarn database:init:prod
   step_done
 fi
 
-step_start "Running migrations"
-yarn database:migrate:prod --force
-step_done
-
 step_start "Flushing cache"
-yarn command:prod cache:flush
+if ! yarn command:prod cache:flush; then
+  echo "Warning: Failed to flush cache before upgrade, but continuing startup..."
+fi
 step_done
 
 step_start "Running upgrade"
-yarn command:prod upgrade
+if ! yarn command:prod upgrade; then
+  echo "Warning: Upgrade completed with errors. Some workspaces may not be fully migrated. Check logs for details."
+fi
 step_done
 
 step_start "Flushing cache"
-yarn command:prod cache:flush
+if ! yarn command:prod cache:flush; then
+  echo "Warning: Failed to flush cache after upgrade, but continuing startup..."
+fi
 step_done
 
 # Only seed on first boot — check if the dev workspace already exists
diff --git a/packages/twenty-docker/twenty/entrypoint.sh b/packages/twenty-docker/twenty/entrypoint.sh
index ff63f2f5f5..fd85657f5d 100755
--- a/packages/twenty-docker/twenty/entrypoint.sh
+++ b/packages/twenty-docker/twenty/entrypoint.sh
@@ -16,9 +16,17 @@ setup_and_migrate_db() {
         yarn database:init:prod
     fi
 
-    yarn command:prod cache:flush
-    yarn command:prod upgrade
-    yarn command:prod cache:flush
+    if ! yarn command:prod cache:flush; then
+        echo "Warning: Failed to flush cache before upgrade, but continuing startup..."
+    fi
+
+    if ! yarn command:prod upgrade; then
+        echo "Warning: Upgrade completed with errors. Some workspaces may not be fully migrated. Check logs for details."
+    fi
+
+    if ! yarn command:prod cache:flush; then
+        echo "Warning: Failed to flush cache after upgrade, but continuing startup..."
+    fi
 
     echo "Successfully migrated DB!"
 }
diff --git a/packages/twenty-server/src/command/command.ts b/packages/twenty-server/src/command/command.ts
index 3a156cc972..7e0e28a267 100644
--- a/packages/twenty-server/src/command/command.ts
+++ b/packages/twenty-server/src/command/command.ts
@@ -13,6 +13,8 @@ async function bootstrap() {
     if (shouldCaptureException(err)) {
       exceptionHandlerService.captureExceptions([err]);
     }
+
+    process.exitCode = 1;
   };
 
   const app = await CommandFactory.createWithoutRunning(CommandModule, {