NginxProxyManager / NginxProxyManager/nginx-proxy-manager

Latest Image brakes my installation (AttributeError: module 'OpenSSL.crypto' has no attribute 'X509Extension')

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Description

Checklist

  • Have you pulled and found the error with jc21/nginx-proxy-manager:latest docker image?
    • Yes
  • Are you sure you're not using someone else's docker image?
    • Yes
  • Have you searched for similar issues (both open and closed)?
    • Yes

Describe the bug
When upgrading to latest image, nginx-proxy-manager starts to not consistent state and doesn't server requests.
I've got several ssl certificates via provider Let's Encrypt – websupport.

There is a related bug.
https://github.com/NginxProxyManager/nginx-proxy-manager/issues/5606
This bug states this error shows during adding a certificate.

My bug has different behaviour, the application will not start (or is in stalled state)

Nginx Proxy Manager Version
latest

To Reproduce
Run latest version

Operating System
linux mint

Additional context


[7/18/2026] [4:52:55 PM] [SSL      ] › ℹ  info      Completed SSL cert renew process
Traceback (most recent call last):
  File "/opt/certbot/bin/certbot", line 3, in <module>
    from certbot.main import main
  File "/opt/certbot/lib/python3.13/site-packages/certbot/main.py", line 6, in <module>
    from certbot._internal import main as internal_main
  File "/opt/certbot/lib/python3.13/site-packages/certbot/_internal/main.py", line 24, in <module>
    from acme import client as acme_client
  File "/opt/certbot/lib/python3.13/site-packages/acme/client.py", line 27, in <module>
    from acme import challenges
  File "/opt/certbot/lib/python3.13/site-packages/acme/challenges.py", line 24, in <module>
    from acme import crypto_util
  File "/opt/certbot/lib/python3.13/site-packages/acme/crypto_util.py", line 504, in <module>
    extensions: Optional[List[crypto.X509Extension]] = None,
                              ^^^^^^^^^^^^^^^^^^^^
  File "/opt/certbot/lib/python3.13/site-packages/cryptography/utils.py", line 76, in __getattr__
    obj = getattr(self._module, name)
AttributeError: module 'OpenSSL.crypto' has no attribute 'X509Extension'
s6-rc: warning: unable to start service prepare: command exited 1
/run/s6/basedir/scripts/rc.init: warning: s6-rc failed to properly bring all the services up! Check your logs (in /run/uncaught-logs/current if you have in-container logging) for more information.
Traceback (most recent call last):
  File "/opt/certbot/bin/certbot", line 3, in <module>
    from certbot.main import main
  File "/opt/certbot/lib/python3.13/site-packages/certbot/main.py", line 6, in <module>
    from certbot._internal import main as internal_main
  File "/opt/certbot/lib/python3.13/site-packages/certbot/_internal/main.py", line 24, in <module>
    from acme import client as acme_client
  File "/opt/certbot/lib/python3.13/site-packages/acme/client.py", line 27, in <module>
    from acme import challenges
  File "/opt/certbot/lib/python3.13/site-packages/acme/challenges.py", line 24, in <module>
    from acme import crypto_util
  File "/opt/certbot/lib/python3.13/site-packages/acme/crypto_util.py", line 504, in <module>
    extensions: Optional[List[crypto.X509Extension]] = None,
                              ^^^^^^^^^^^^^^^^^^^^
  File "/opt/certbot/lib/python3.13/site-packages/cryptography/utils.py", line 76, in __getattr__
    obj = getattr(self._module, name)
AttributeError: module 'OpenSSL.crypto' has no attribute 'X509Extension'
s6-rc: warning: unable to start service prepare: command exited 1
/run/s6/basedir/scripts/rc.init: warning: s6-rc failed to properly bring all the services up! Check your logs (in /run/uncaught-logs/current if you have in-container logging) for more information.

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First steps

  1. Read the whole issue, then the project's contributing guide.
  2. Comment on the issue to say you are picking it up — it saves two people doing the same work.
  3. Fork the repository and make your change on a branch.
  4. Open a pull request that references the issue number.

Research direction

The failure occurs during the latest Docker image's Certbot startup at /opt/certbot/bin/certbot, importing certbot.main, acme/crypto_util.py, and OpenSSL.crypto.X509Extension. Reproduce with the latest image and inspect the dependency versions and startup logs; done means the service starts consistently without this traceback and certificate renewal can run.

Written by the indexing model from the issue text.

Assessment

Tech stack
docker, python
Domain
devops, security
Issue type
Bug
Difficulty
4/5
Estimated time
3-5 days
Activity status
Quiet
Clarity
Mostly clear
Newbie friendliness
48/100

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