diff --git a/sqlmesh/core/state_sync/db/migrator.py b/sqlmesh/core/state_sync/db/migrator.py
index aaabeac5d9..dc4022fb1a 100644
--- a/sqlmesh/core/state_sync/db/migrator.py
+++ b/sqlmesh/core/state_sync/db/migrator.py
@@ -120,19 +120,25 @@ def migrate(
             if skip_backup:
                 logger.error("Backup was skipped so no rollback was attempted.")
             else:
-                self.rollback()
+                try:
+                    self.rollback()
+                except Exception:
+                    logger.exception("Migration rollback failed.")
 
-            analytics.collector.on_migration_end(
-                from_sqlmesh_version=versions.sqlmesh_version,
-                state_sync_type=self.engine_adapter.dialect,
-                migration_time_sec=time.perf_counter() - migration_start_ts,
-                error=e,
-            )
+            try:
+                analytics.collector.on_migration_end(
+                    from_sqlmesh_version=versions.sqlmesh_version,
+                    state_sync_type=self.engine_adapter.dialect,
+                    migration_time_sec=time.perf_counter() - migration_start_ts,
+                    error=e,
+                )
+            except Exception:
+                logger.exception("Failed to record the migration end analytics event.")
 
             self.console.log_migration_status(success=False)
             if isinstance(e, StateMigrationError):
                 raise
-            raise SQLMeshError("SQLMesh migration failed.") from e
+            raise SQLMeshError(f"SQLMesh migration failed: {e}") from e
 
         self.console.log_migration_status()
 
diff --git a/tests/core/state_sync/test_state_sync.py b/tests/core/state_sync/test_state_sync.py
index 32a359f667..f76211663f 100644
--- a/tests/core/state_sync/test_state_sync.py
+++ b/tests/core/state_sync/test_state_sync.py
@@ -11,6 +11,7 @@
 from pytest_mock.plugin import MockerFixture
 from sqlglot import exp
 
+from sqlmesh.core import analytics
 from sqlmesh.core import constants as c
 from sqlmesh.core.config import EnvironmentSuffixTarget
 from sqlmesh.core.dialect import parse_one
@@ -2854,6 +2855,28 @@ def test_first_migration_failure(duck_conn, mocker: MockerFixture, tmp_path) ->
     assert not state_sync.engine_adapter.table_exists(state_sync.interval_state.intervals_table)
 
 
+def test_migration_failure_after_update_versions(
+    duck_conn, mocker: MockerFixture, tmp_path
+) -> None:
+    state_sync = EngineAdapterStateSync(
+        create_engine_adapter(lambda: duck_conn, "duckdb"),
+        schema=c.SQLMESH,
+        cache_dir=tmp_path / c.CACHE,
+    )
+    # The first call happens inside the try block right after update_versions() and
+    # raises; the second call happens in the exception handler and succeeds.
+    mocker.patch.object(
+        analytics.collector,
+        "on_migration_end",
+        side_effect=[Exception("mocked error"), None],
+    )
+    with pytest.raises(SQLMeshError, match="SQLMesh migration failed.") as exc_info:
+        state_sync.migrate()
+    assert "mocked error" in str(exc_info.value)
+    assert isinstance(exc_info.value.__cause__, Exception)
+    assert "mocked error" in str(exc_info.value.__cause__)
+
+
 def test_migrate_rows(state_sync: EngineAdapterStateSync, mocker: MockerFixture) -> None:
     state_sync.engine_adapter.replace_query(
         "sqlmesh._versions",