diff --git a/backend/alembic/versions/da42808081e3_migrate_jira_connectors_to_new_format.py b/backend/alembic/versions/da42808081e3_migrate_jira_connectors_to_new_format.py
index a705e637b54..0a1dc174371 100644
--- a/backend/alembic/versions/da42808081e3_migrate_jira_connectors_to_new_format.py
+++ b/backend/alembic/versions/da42808081e3_migrate_jira_connectors_to_new_format.py
@@ -127,5 +127,5 @@ def downgrade() -> None:
                 WHERE id = :id
                 """
             ),
-            {"id": connector_id, "old_config": old_config},
+            {"id": connector_id, "old_config": json.dumps(old_config)},
         )
diff --git a/backend/tests/integration/tests/migrations/test_migrations.py b/backend/tests/integration/tests/migrations/test_migrations.py
index 19b6fb1fba6..238d5ef5f5b 100644
--- a/backend/tests/integration/tests/migrations/test_migrations.py
+++ b/backend/tests/integration/tests/migrations/test_migrations.py
@@ -1,3 +1,5 @@
+import json
+
 import pytest
 from sqlalchemy import text
 
@@ -123,3 +125,196 @@ def test_fix_capitalization_migration() -> None:
         assert len(results) == 2
         assert results[0].external_user_group_ids == ["group1", "group2", "group3"]
         assert results[1].external_user_group_ids == ["upper1", "upper2", "upper3"]
+
+
+def test_jira_connector_migration() -> None:
+    """Test that the da42808081e3 migration correctly updates Jira connector configurations"""
+    # Reset the database and run migrations up to the migration before the Jira connector change
+    downgrade_postgres(
+        database="postgres", config_name="alembic", revision="base", clear_data=True
+    )
+    upgrade_postgres(
+        database="postgres",
+        config_name="alembic",
+        # Upgrade it to the migration before the Jira connector change
+        revision="f13db29f3101",
+    )
+
+    # Insert test data with various Jira connector configurations
+    test_data = [
+        {
+            "id": 1,
+            "name": "jira_connector_1",
+            "source": "JIRA",
+            "connector_specific_config": {
+                "jira_project_url": "https://example.atlassian.net/projects/PROJ",
+                "comment_email_blacklist": ["test@example.com"],
+                "batch_size": 100,
+                "labels_to_skip": ["skip-me"],
+            },
+        },
+        {
+            "id": 2,
+            "name": "jira_connector_2",
+            "source": "JIRA",
+            "connector_specific_config": {
+                "jira_project_url": "https://other.atlassian.net/projects/OTHER"
+            },
+        },
+        {
+            "id": 3,
+            "name": "jira_connector_3",
+            "source": "JIRA",
+            "connector_specific_config": {
+                "jira_project_url": "https://example.atlassian.net/projects/TEST",
+                "batch_size": 50,
+            },
+        },
+    ]
+
+    # Insert the test data
+    with get_session_context_manager() as db_session:
+        for connector in test_data:
+            db_session.execute(
+                text(
+                    """
+                    INSERT INTO connector (
+                        id,
+                        name,
+                        source,
+                        connector_specific_config
+                    )
+                    VALUES (
+                        :id,
+                        :name,
+                        :source,
+                        :config
+                    )
+                    """
+                ),
+                {
+                    "id": connector["id"],
+                    "name": connector["name"],
+                    "source": connector["source"],
+                    "config": json.dumps(connector["connector_specific_config"]),
+                },
+            )
+        db_session.commit()
+
+    # Verify the data was inserted correctly
+    with get_session_context_manager() as db_session:
+        results = db_session.execute(
+            text(
+                """
+                SELECT id, connector_specific_config
+                FROM connector
+                WHERE source = 'JIRA'
+                ORDER BY id
+                """
+            )
+        ).fetchall()
+
+        # Verify initial state
+        assert len(results) == 3
+        assert (
+            results[0].connector_specific_config
+            == test_data[0]["connector_specific_config"]
+        )
+        assert (
+            results[1].connector_specific_config
+            == test_data[1]["connector_specific_config"]
+        )
+        assert (
+            results[2].connector_specific_config
+            == test_data[2]["connector_specific_config"]
+        )
+
+    # Run migrations again to apply the Jira connector change
+    upgrade_postgres(
+        database="postgres", config_name="alembic", revision="da42808081e3"
+    )
+
+    # Verify the upgrade was applied correctly
+    with get_session_context_manager() as db_session:
+        results = db_session.execute(
+            text(
+                """
+                SELECT id, connector_specific_config
+                FROM connector
+                WHERE source = 'JIRA'
+                ORDER BY id
+                """
+            )
+        ).fetchall()
+
+        # Verify new format
+        assert len(results) == 3
+
+        # First connector - full config
+        config_0 = results[0].connector_specific_config
+        assert config_0["jira_base_url"] == "https://example.atlassian.net"
+        assert config_0["project_key"] == "PROJ"
+        assert config_0["comment_email_blacklist"] == ["test@example.com"]
+        assert config_0["batch_size"] == 100
+        assert config_0["labels_to_skip"] == ["skip-me"]
+
+        # Second connector - minimal config
+        config_1 = results[1].connector_specific_config
+        assert config_1["jira_base_url"] == "https://other.atlassian.net"
+        assert config_1["project_key"] == "OTHER"
+        assert "comment_email_blacklist" not in config_1
+        assert "batch_size" not in config_1
+        assert "labels_to_skip" not in config_1
+
+        # Third connector - partial config
+        config_2 = results[2].connector_specific_config
+        assert config_2["jira_base_url"] == "https://example.atlassian.net"
+        assert config_2["project_key"] == "TEST"
+        assert config_2["batch_size"] == 50
+        assert "comment_email_blacklist" not in config_2
+        assert "labels_to_skip" not in config_2
+
+    # Test downgrade path
+    downgrade_postgres(
+        database="postgres", config_name="alembic", revision="f13db29f3101"
+    )
+
+    # Verify the downgrade was applied correctly
+    with get_session_context_manager() as db_session:
+        results = db_session.execute(
+            text(
+                """
+                SELECT id, connector_specific_config
+                FROM connector
+                WHERE source = 'JIRA'
+                ORDER BY id
+                """
+            )
+        ).fetchall()
+
+        # Verify reverted to old format
+        assert len(results) == 3
+
+        # First connector - full config
+        config_0 = results[0].connector_specific_config
+        assert (
+            config_0["jira_project_url"]
+            == "https://example.atlassian.net/projects/PROJ"
+        )
+        assert config_0["comment_email_blacklist"] == ["test@example.com"]
+        assert config_0["batch_size"] == 100
+        assert config_0["labels_to_skip"] == ["skip-me"]
+
+        # Second connector - minimal config
+        config_1 = results[1].connector_specific_config
+        assert (
+            config_1["jira_project_url"] == "https://other.atlassian.net/projects/OTHER"
+        )
+
+        # Third connector - partial config
+        config_2 = results[2].connector_specific_config
+        assert (
+            config_2["jira_project_url"]
+            == "https://example.atlassian.net/projects/TEST"
+        )
+        assert config_2["batch_size"] == 50