troyharvey opened a new issue, #26834:
URL: https://github.com/apache/airflow/issues/26834

   ### Apache Airflow version
   
   2.4.1
   
   ### What happened
   
   Running `airflow db upgrade` on an Airflow installation with 100 DAGs fails 
with this error:
   
   ```
   ERROR [airflow.models.dagbag.DagBag] Failed to write serialized DAG: 
/usr/local/airflow/dags/REDACTED.py
   Traceback (most recent call last):
     File "/usr/local/lib/python3.9/site-packages/airflow/models/dagbag.py", 
line 615, in _serialize_dag_capturing_errors
       dag_was_updated = SerializedDagModel.write_dag(
     File "/usr/local/lib/python3.9/site-packages/airflow/utils/session.py", 
line 72, in wrapper
       return func(*args, **kwargs)
     File 
"/usr/local/lib/python3.9/site-packages/airflow/models/serialized_dag.py", line 
146, in write_dag
       session.query(literal(True))
     File "/usr/local/lib/python3.9/site-packages/sqlalchemy/orm/query.py", 
line 2810, in first
       return self.limit(1)._iter().first()
     File "/usr/local/lib/python3.9/site-packages/sqlalchemy/orm/query.py", 
line 2894, in _iter
       result = self.session.execute(
     File "/usr/local/lib/python3.9/site-packages/sqlalchemy/orm/session.py", 
line 1688, in execute
       conn = self._connection_for_bind(bind)
     File "/usr/local/lib/python3.9/site-packages/sqlalchemy/orm/session.py", 
line 1529, in _connection_for_bind
       return self._transaction._connection_for_bind(
     File "/usr/local/lib/python3.9/site-packages/sqlalchemy/orm/session.py", 
line 721, in _connection_for_bind
       self._assert_active()
     File "/usr/local/lib/python3.9/site-packages/sqlalchemy/orm/session.py", 
line 601, in _assert_active
       raise sa_exc.PendingRollbackError(
   sqlalchemy.exc.PendingRollbackError: This Session's transaction has been 
rolled back due to a previous exception during flush. To begin a new 
transaction with this Session, first issue Session.rollback(). Original 
exception was: (psycopg2.errors.UniqueViolation) duplicate key value violates 
unique constraint "serialized_dag_pkey"
   DETAIL:  Key (dag_id)=(REDACTED) already exists.
   
   [SQL: INSERT INTO serialized_dag (dag_id, fileloc, fileloc_hash, data, 
data_compressed, last_updated, dag_hash, ...
   ```
   
   ### What you think should happen instead
   
   `airflow db upgrade` should successfully reserialize DAGs at the end of the 
upgrade just like the `airflow dags reserialize` command.
   
   ### How to reproduce
   
   1. Upgrade to `airflow 2.4.1` on an existing codebase
   2. Run `airflow db upgrade`
   
   ### Operating System
   
   Debian GNU/Linux 10 (buster)
   
   ### Versions of Apache Airflow Providers
   
   ```
   apache-airflow-providers-amazon==5.1.0
   apache-airflow-providers-celery==3.0.0
   apache-airflow-providers-cncf-kubernetes==4.3.0
   apache-airflow-providers-common-sql==1.2.0
   apache-airflow-providers-datadog==3.0.0
   apache-airflow-providers-ftp==3.1.0
   apache-airflow-providers-http==4.0.0
   apache-airflow-providers-imap==3.0.0
   apache-airflow-providers-postgres==5.2.1
   apache-airflow-providers-redis==3.0.0
   apache-airflow-providers-sendgrid==3.0.0
   apache-airflow-providers-sftp==4.0.0
   apache-airflow-providers-slack==5.1.0
   apache-airflow-providers-sqlite==3.2.1
   apache-airflow-providers-ssh==3.1.0
   ```
   
   ### Deployment
   
   Other Docker-based deployment
   
   ### Deployment details
   
   k8s deployment
   
   ### Anything else
   
   Fails consistently in these two scenarios:
   
   1. Run db upgrade only:
   
           airflow db upgrade
   
   1. Run along with reserialize
   
           airflow dags reserialize --clear-only
           airflow db upgrade
   
   ### Are you willing to submit PR?
   
   - [X] Yes I am willing to submit a PR!
   
   ### Code of Conduct
   
   - [X] I agree to follow this project's [Code of 
Conduct](https://github.com/apache/airflow/blob/main/CODE_OF_CONDUCT.md)
   


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