chrisdonlan opened a new issue, #58337:
URL: https://github.com/apache/airflow/issues/58337

   ### Apache Airflow version
   
   3.1.2
   
   ### If "Other Airflow 2/3 version" selected, which one?
   
   _No response_
   
   ### What happened?
   
   With FIPS mode enabled, `apt update` may not be called successfully, as the 
image was originally built without `FIPS` enabled. 
   
   ### What you think should happen instead?
   
   The image should be built with FIPS turned on to begin with, so that when 
extending `airflow` base image with additional dependencies, the `Fatal error: 
requiested algo not in md context` error does not appear during an `apt-get 
update`. 
   
   ### How to reproduce
   
   Turn `FIPS` mode on. Descend from any image after `bullseye`, when the 
exception allowing `md5` verification with FIPS enabled was removed. 
   
   ```
   FROM apache/airflow:latest
   
   USER root
   RUN apt-get update
   ```
   
   
   
   ### Operating System
   
   Redhat 9.6
   
   ### Versions of Apache Airflow Providers
   
   Not relevant
   
   ### Deployment
   
   Other 3rd-party Helm chart
   
   ### Deployment details
   
   Not relevant -- just need to enable FIPS during your base image build.  I 
have a pretty beefy machine that is crapping out on the `Dockerfile.ci` build 
during `lto-wrapper` (link time optimization) with args:
   
   ```
   AIRFLOW_PYTHON_VERSION: 3.13.9
   BASE_IMAGE: debian:bookworm-slim
   # and the current commit hash from docker.io
   ```
   
   So I've had to modify the build to disable link time optimization during 
python compilation. If you could break up the "install_os_dependencies.sh" 
script into layers so that the build can at least ratchet forward, that would 
make getting something in place more straightforward.
   
   
   ### Anything else?
   
   _No response_
   
   ### Are you willing to submit PR?
   
   - [ ] 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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