diff --git a/litellm-proxy-extras/litellm_proxy_extras/migrations/20250603210143_cascade_budget_changes/migration.sql b/litellm-proxy-extras/litellm_proxy_extras/migrations/20250603210143_cascade_budget_changes/migration.sql
index 0fbb5024dde..ef53fbf3f4a 100644
--- a/litellm-proxy-extras/litellm_proxy_extras/migrations/20250603210143_cascade_budget_changes/migration.sql
+++ b/litellm-proxy-extras/litellm_proxy_extras/migrations/20250603210143_cascade_budget_changes/migration.sql
@@ -1,5 +1,10 @@
 -- DropForeignKey
-ALTER TABLE "LiteLLM_TeamMembership" DROP CONSTRAINT "LiteLLM_TeamMembership_budget_id_fkey";
+DO $$
+BEGIN
+    IF EXISTS (SELECT 1 FROM pg_constraint WHERE conname = 'LiteLLM_TeamMembership_budget_id_fkey') THEN
+        ALTER TABLE "LiteLLM_TeamMembership" DROP CONSTRAINT "LiteLLM_TeamMembership_budget_id_fkey";
+    END IF;
+END $$;
 
 -- AddForeignKey
 DO $$
diff --git a/litellm-proxy-extras/litellm_proxy_extras/migrations/20250625145206_cascade_budget_and_loosen_managed_file_json/migration.sql b/litellm-proxy-extras/litellm_proxy_extras/migrations/20250625145206_cascade_budget_and_loosen_managed_file_json/migration.sql
index 3c113a21f79..75d7e0e74b1 100644
--- a/litellm-proxy-extras/litellm_proxy_extras/migrations/20250625145206_cascade_budget_and_loosen_managed_file_json/migration.sql
+++ b/litellm-proxy-extras/litellm_proxy_extras/migrations/20250625145206_cascade_budget_and_loosen_managed_file_json/migration.sql
@@ -1,5 +1,10 @@
 -- DropForeignKey
-ALTER TABLE "LiteLLM_TeamMembership" DROP CONSTRAINT "LiteLLM_TeamMembership_budget_id_fkey";
+DO $$
+BEGIN
+    IF EXISTS (SELECT 1 FROM pg_constraint WHERE conname = 'LiteLLM_TeamMembership_budget_id_fkey') THEN
+        ALTER TABLE "LiteLLM_TeamMembership" DROP CONSTRAINT "LiteLLM_TeamMembership_budget_id_fkey";
+    END IF;
+END $$;
 
 -- AlterTable
 ALTER TABLE "LiteLLM_ManagedFileTable" ALTER COLUMN "file_object" DROP NOT NULL;
diff --git a/litellm-proxy-extras/litellm_proxy_extras/utils.py b/litellm-proxy-extras/litellm_proxy_extras/utils.py
index 7a14a109530..5b4feed2564 100644
--- a/litellm-proxy-extras/litellm_proxy_extras/utils.py
+++ b/litellm-proxy-extras/litellm_proxy_extras/utils.py
@@ -422,9 +422,8 @@ class ProxyExtrasDBManager:
                                         failed_migration
                                     )
                                     logger.info(
-                                        f"✅ Migration {failed_migration} resolved."
+                                        f"✅ Migration {failed_migration} resolved, retrying to apply remaining migrations"
                                     )
-                                    return True
                                 else:
                                     logger.info(
                                         f"Found failed migration: {failed_migration}, marking as rolled back"
@@ -534,8 +533,10 @@ class ProxyExtrasDBManager:
                                         ProxyExtrasDBManager._resolve_specific_migration(
                                             migration_name
                                         )
-                                        logger.info("✅ Migration resolved.")
-                                        return True
+                                        logger.info(
+                                            f"✅ Migration {migration_name} resolved, "
+                                            f"retrying to apply remaining migrations"
+                                        )
                                     except (subprocess.CalledProcessError, subprocess.TimeoutExpired) as resolve_err:
                                         logger.warning(
                                             f"Failed to resolve migration {migration_name}: {resolve_err}"
diff --git a/tests/litellm-proxy-extras/test_litellm_proxy_extras_utils.py b/tests/litellm-proxy-extras/test_litellm_proxy_extras_utils.py
index 1fc93cd4966..05f4b8a98e1 100644
--- a/tests/litellm-proxy-extras/test_litellm_proxy_extras_utils.py
+++ b/tests/litellm-proxy-extras/test_litellm_proxy_extras_utils.py
@@ -275,3 +275,21 @@ class TestMigrationSQLIdempotency:
             "ADD CONSTRAINT without DO $$ IF NOT EXISTS guard found in migrations:\n"
             + "\n".join(violations)
         )
+
+    def test_drop_constraint_is_guarded(self, all_migrations):
+        """DROP CONSTRAINT must be inside a DO $$ IF EXISTS block"""
+        violations = []
+        for migration_name, sql in all_migrations:
+            lines = sql.splitlines()
+            in_do_block = False
+            for line_num, line in enumerate(lines, 1):
+                if re.search(r"DO\s+\$\$", line, re.IGNORECASE):
+                    in_do_block = True
+                if re.search(r"END\s+\$\$", line, re.IGNORECASE):
+                    in_do_block = False
+                if re.search(r"DROP\s+CONSTRAINT\s+", line, re.IGNORECASE) and not in_do_block:
+                    violations.append(f"  {migration_name}:{line_num}: {line.strip()}")
+        assert not violations, (
+            "DROP CONSTRAINT without DO $$ IF EXISTS guard found in migrations:\n"
+            + "\n".join(violations)
+        )