diff --git a/migrations/tenant/0025-custom-metadata.sql b/migrations/tenant/0025-custom-metadata.sql
index b18d92f6..97fe6507 100644
--- a/migrations/tenant/0025-custom-metadata.sql
+++ b/migrations/tenant/0025-custom-metadata.sql
@@ -1,2 +1,3 @@
+---SYNC---
 ALTER TABLE storage.objects ADD COLUMN user_metadata jsonb NULL;
 ALTER TABLE storage.s3_multipart_uploads ADD COLUMN user_metadata jsonb NULL;
\ No newline at end of file
diff --git a/src/http/plugins/db.ts b/src/http/plugins/db.ts
index 35697ae1..963c9ae9 100644
--- a/src/http/plugins/db.ts
+++ b/src/http/plugins/db.ts
@@ -10,6 +10,7 @@ import {
   getPostgresConnection,
   progressiveMigrations,
   runMigrationsOnTenant,
+  hasMissingSyncMigration,
 } from '@internal/database'
 import { verifyJWT } from '@internal/auth'
 import { logSchema } from '@internal/monitoring'
@@ -201,19 +202,25 @@ export const migrations = fastifyPlugin(async function migrations(fastify) {
         return
       }
 
+      const needsToRunMigrationsNow = await hasMissingSyncMigration(request.tenantId)
+
       // if the tenant is not marked as stale, add it to the progressive migrations queue
-      if (tenant.migrationStatus !== TenantMigrationStatus.FAILED_STALE) {
+      if (
+        !needsToRunMigrationsNow &&
+        tenant.migrationStatus !== TenantMigrationStatus.FAILED_STALE
+      ) {
         progressiveMigrations.addTenant(request.tenantId)
         return
       }
 
-      // if the tenant is marked as stale, try running the migrations
-      migrationsMutex(request.tenantId, async () => {
+      // if the tenant is marked as stale or there are pending SYNC migrations,
+      // try running the migrations
+      await migrationsMutex(request.tenantId, async () => {
         if (tenant.syncMigrationsDone || migrationsUpToDate) {
           return
         }
 
-        await runMigrationsOnTenant(tenant.databaseUrl, request.tenantId, false)
+        await runMigrationsOnTenant(tenant.databaseUrl, request.tenantId, needsToRunMigrationsNow)
           .then(async () => {
             await updateTenantMigrationsState(request.tenantId)
             tenant.syncMigrationsDone = true
@@ -231,9 +238,14 @@ export const migrations = fastifyPlugin(async function migrations(fastify) {
               }
             )
           })
-          .catch(() => {
-            // no-op
-          })
+      }).catch((e) => {
+        logSchema.error(fastify.log, `[Migrations] Error running migrations ${request.tenantId} `, {
+          type: 'migrations',
+          error: e,
+          metadata: JSON.stringify({
+            strategy: 'progressive',
+          }),
+        })
       })
     })
   }
diff --git a/src/internal/database/migrations/migrate.ts b/src/internal/database/migrations/migrate.ts
index b78746a7..c84901d7 100644
--- a/src/internal/database/migrations/migrate.ts
+++ b/src/internal/database/migrations/migrate.ts
@@ -7,7 +7,7 @@ import { BasicPgClient, Migration } from 'postgres-migrations/dist/types'
 import { validateMigrationHashes } from 'postgres-migrations/dist/validation'
 import { runMigration } from 'postgres-migrations/dist/run-migration'
 import { searchPath } from '../connection'
-import { listTenantsToMigrate } from '../tenant'
+import { getTenantConfig, listTenantsToMigrate, TenantMigrationStatus } from '../tenant'
 import { multitenantKnex } from '../multitenant-db'
 import { ProgressiveMigrations } from './progressive'
 import { RunMigrationsOnTenants } from '@storage/events'
@@ -80,6 +80,28 @@ export async function lastMigrationName() {
   return migrations[migrations.length - 1].name
 }
 
+export async function hasMissingSyncMigration(tenantId: string) {
+  const { migrationVersion, migrationStatus } = await getTenantConfig(tenantId)
+  const migrations = await loadMigrationFilesCached('./migrations/tenant')
+
+  if (!migrationStatus) {
+    return migrations.some((m) => {
+      return m.contents.includes('---SYNC---')
+    })
+  }
+
+  const indexLastMigration = migrations.findIndex((m) => m.name === migrationVersion)
+
+  if (indexLastMigration === -1) {
+    return true
+  }
+
+  const migrationAfterLast = migrations.slice(indexLastMigration + 1)
+  return migrationAfterLast.some((m) => {
+    return m.contents.includes('---SYNC---')
+  })
+}
+
 /**
  * Runs migrations for all tenants
  * only one instance at the time is allowed to run
@@ -369,7 +391,17 @@ function withAdvisoryLock<T>(
     try {
       try {
         let acquired = false
+        let tries = 1
+
+        const timeout = 3000
+        const start = Date.now()
+
         while (!acquired) {
+          const elapsed = Date.now() - start
+          if (elapsed > timeout) {
+            throw ERRORS.LockTimeout()
+          }
+
           const lockResult = await client.query(
             'SELECT pg_try_advisory_lock(-8525285245963000605);'
           )
@@ -377,11 +409,13 @@ function withAdvisoryLock<T>(
             acquired = true
           } else {
             if (waitForLock) {
-              await new Promise((res) => setTimeout(res, 700))
+              await new Promise((res) => setTimeout(res, 20 * tries))
             } else {
               return [] as unknown as Promise<T>
             }
           }
+
+          tries++
         }
       } catch (e) {
         throw e