# Google SSO AttributeError: module 'OpenSSL.crypto' has no attribute 'sign' **URL:** \ **Category:** Pritunl VPN\ **Tags:** pritunl-endpoint, pritunl\ **Created:** [February 21, 2025, 5:38pm UTC](https://forum.pritunl.com/t/google-sso-attributeerror-module-openssl-crypto-has-no-attribute-sign/3057 "2025-02-21T17:38:19Z")\ **Posts on this page:** 4\ **Page:** 1
**Author:** ![thanisms](https://forum.pritunl.com/user_avatar/forum.pritunl.com/thanisms/32/1205_2.png) [@thanisms](https://forum.pritunl.com/u/thanisms)\ **Post date:** [February 21, 2025, 5:38pm UTC](https://forum.pritunl.com/t/google-sso-attributeerror-module-openssl-crypto-has-no-attribute-sign/3057/1 "2025-02-21T17:38:19Z")
I have Ubuntu 24.04.2 LTS, installed pritunl server with enterprise license After i updated my os , i am getting the following error Can you please help ? tail -f /var/log/pritunl.log [autumn-meadow-6140][2025-02-21 16:57:54,090][ERROR] Exception on /sso/callback [GET] Traceback (most recent call last): File “/usr/lib/pritunl/usr/lib/python3.9/site-packages/flask/app.py”, line 2190, in wsgi\_app response = self.full\_dispatch\_request() File “/usr/lib/pritunl/usr/lib/python3.9/site-packages/flask/app.py”, line 1486, in full\_dispatch\_request rv = self.handle\_user\_exception(e) File “/usr/lib/pritunl/usr/lib/python3.9/site-packages/flask/app.py”, line 1484, in full\_dispatch\_request rv = self.dispatch\_request() File “/usr/lib/pritunl/usr/lib/python3.9/site-packages/flask/app.py”, line 1469, in dispatch\_request return self.ensure\_sync(self.view\_functions[rule.endpoint])(\*\*view\_args) File “/usr/lib/pritunl/usr/lib/python3.9/site-packages/pritunl/auth/app.py”, line 26, in \_wrapped return call(\*args, \*\*kwargs) File “/usr/lib/pritunl/usr/lib/python3.9/site-packages/pritunl/handlers/sso.py”, line 664, in sso\_callback\_get valid, google\_groups = sso.verify\_google(username) File “/usr/lib/pritunl/usr/lib/python3.9/site-packages/pritunl/sso/google.py”, line 42, in verify\_google data = service.users().get(userKey=user\_email).execute() File “/usr/lib/pritunl/usr/lib/python3.9/site-packages/googleapiclient/\_helpers.py”, line 130, in positional\_wrapper return wrapped(\*args, \*\*kwargs) File “/usr/lib/pritunl/usr/lib/python3.9/site-packages/googleapiclient/http.py”, line 923, in execute resp, content = \_retry\_request( File “/usr/lib/pritunl/usr/lib/python3.9/site-packages/googleapiclient/http.py”, line 191, in \_retry\_request resp, content = http.request(uri, method, \*args, \*\*kwargs) File “/usr/lib/pritunl/usr/lib/python3.9/site-packages/oauth2client/transport.py”, line 159, in new\_request credentials.\_refresh(orig\_request\_method) File “/usr/lib/pritunl/usr/lib/python3.9/site-packages/oauth2client/client.py”, line 749, in \_refresh self.\_do\_refresh\_request(http) File “/usr/lib/pritunl/usr/lib/python3.9/site-packages/oauth2client/client.py”, line 774, in \_do\_refresh\_request body = self.\_generate\_refresh\_request\_body() File “/usr/lib/pritunl/usr/lib/python3.9/site-packages/oauth2client/client.py”, line 1484, in \_generate\_refresh\_request\_body assertion = self.\_generate\_assertion() File “/usr/lib/pritunl/usr/lib/python3.9/site-packages/oauth2client/service\_account.py”, line 384, in \_generate\_assertion return crypt.make\_signed\_jwt(self.\_signer, payload, File “/usr/lib/pritunl/usr/lib/python3.9/site-packages/oauth2client/crypt.py”, line 97, in make\_signed\_jwt signature = signer.sign(signing\_input) File “/usr/lib/pritunl/usr/lib/python3.9/site-packages/oauth2client/\_openssl\_crypt.py”, line 97, in sign return crypto.sign(self.\_key, message, ‘sha256’) File “/usr/lib/pritunl/usr/lib/python3.9/site-packages/cryptography/utils.py”, line 68, in **getattr** obj = getattr(self.\_module, attr) AttributeError: module ‘OpenSSL.crypto’ has no attribute ‘sign’ [autumn-meadow-6140][2025-02-21 16:57:54,090][ERROR] Exception on /sso/callback [GET] Traceback (most recent call last): File “/usr/lib/pritunl/usr/lib/python3.9/site-packages/flask/app.py”, line 2190, in wsgi\_app response = self.full\_dispatch\_request() File “/usr/lib/pritunl/usr/lib/python3.9/site-packages/flask/app.py”, line 1486, in full\_dispatch\_request rv = self.handle\_user\_exception(e) File “/usr/lib/pritunl/usr/lib/python3.9/site-packages/flask/app.py”, line 1484, in full\_dispatch\_request rv = self.dispatch\_request() File “/usr/lib/pritunl/usr/lib/python3.9/site-packages/flask/app.py”, line 1469, in dispatch\_request return self.ensure\_sync(self.view\_functions[rule.endpoint])(\*\*view\_args) File “/usr/lib/pritunl/usr/lib/python3.9/site-packages/pritunl/auth/app.py”, line 26, in \_wrapped return call(\*args, \*\*kwargs) File “/usr/lib/pritunl/usr/lib/python3.9/site-packages/pritunl/handlers/sso.py”, line 664, in sso\_callback\_get valid, google\_groups = sso.verify\_google(username) File “/usr/lib/pritunl/usr/lib/python3.9/site-packages/pritunl/sso/google.py”, line 42, in verify\_google data = service.users().get(userKey=user\_email).execute() File “/usr/lib/pritunl/usr/lib/python3.9/site-packages/googleapiclient/\_helpers.py”, line 130, in positional\_wrapper return wrapped(\*args, \*\*kwargs) File “/usr/lib/pritunl/usr/lib/python3.9/site-packages/googleapiclient/http.py”, line 923, in execute resp, content = \_retry\_request( File “/usr/lib/pritunl/usr/lib/python3.9/site-packages/googleapiclient/http.py”, line 191, in \_retry\_request resp, content = http.request(uri, method, \*args, \*\*kwargs) File “/usr/lib/pritunl/usr/lib/python3.9/site-packages/oauth2client/transport.py”, line 159, in new\_request credentials.\_refresh(orig\_request\_method) File “/usr/lib/pritunl/usr/lib/python3.9/site-packages/oauth2client/client.py”, line 749, in \_refresh self.\_do\_refresh\_request(http) File “/usr/lib/pritunl/usr/lib/python3.9/site-packages/oauth2client/client.py”, line 774, in \_do\_refresh\_request body = self.\_generate\_refresh\_request\_body() File “/usr/lib/pritunl/usr/lib/python3.9/site-packages/oauth2client/client.py”, line 1484, in \_generate\_refresh\_request\_body assertion = self.\_generate\_assertion() File “/usr/lib/pritunl/usr/lib/python3.9/site-packages/oauth2client/service\_account.py”, line 384, in \_generate\_assertion return crypt.make\_signed\_jwt(self.\_signer, payload, File “/usr/lib/pritunl/usr/lib/python3.9/site-packages/oauth2client/crypt.py”, line 97, in make\_signed\_jwt signature = signer.sign(signing\_input) File “/usr/lib/pritunl/usr/lib/python3.9/site-packages/oauth2client/\_openssl\_crypt.py”, line 97, in sign return crypto.sign(self.\_key, message, ‘sha256’) File “/usr/lib/pritunl/usr/lib/python3.9/site-packages/cryptography/utils.py”, line 68, in **getattr** obj = getattr(self.\_module, attr) AttributeError: module ‘OpenSSL.crypto’ has no attribute ‘sign’ ---
**Author:** ![zach](https://forum.pritunl.com/user_avatar/forum.pritunl.com/zach/32/1105_2.png) [@zach](https://forum.pritunl.com/u/zach)\ **Post date:** [February 22, 2025, 6:36am UTC](https://forum.pritunl.com/t/google-sso-attributeerror-module-openssl-crypto-has-no-attribute-sign/3057/2 "2025-02-22T06:36:39Z")
The recent updated pyOpenSSL is incompatible with oauth2client. This will be fixed in an update in a few hours. It can be fixed on the server by editing `sudo nano /usr/lib/pritunl/usr/lib/python3.9/site-packages/pritunl/sso/google.py` holding ctrl+k to clear the file then replacing it with the code below. Once done run `sudo systemctl restart pritunl`. ```auto from pritunl import settings from pritunl import utils import json import io from google.oauth2 import service_account from googleapiclient import discovery def verify_google(user_email): user_domain = user_email.split('@')[-1] if not isinstance(settings.app.sso_match, list): raise TypeError('Invalid sso match') if not user_domain in settings.app.sso_match: return False, [] google_key = settings.app.sso_google_key google_email = settings.app.sso_google_email if not google_key or not google_email: return True, [] data = json.loads(google_key) credentials = service_account.Credentials.from_service_account_info( data, scopes=[ 'https://www.googleapis.com/auth/admin.directory.user.readonly', 'https://www.googleapis.com/auth/admin.directory.group.readonly', ], ) delegated_credentials = credentials.with_subject(google_email) service = discovery.build( 'admin', 'directory_v1', credentials=delegated_credentials) data = service.users().get(userKey=user_email).execute() if data.get('suspended'): return False, [] results = service.groups().list(userKey=user_email, maxResults=settings.app.sso_google_groups_max).execute() groups = [] for group in results.get('groups') or []: groups.append(utils.filter_unicode(group['name'])) return True, groups ``` ---
**Author:** ![jim](https://forum.pritunl.com/letter_avatar_proxy/v4/letter/j/ac91a4/32.png) [@jim](https://forum.pritunl.com/u/jim)\ **Post date:** [February 22, 2025, 2:08pm UTC](https://forum.pritunl.com/t/google-sso-attributeerror-module-openssl-crypto-has-no-attribute-sign/3057/3 "2025-02-22T14:08:28Z")
Thanks for posting this quick fix. Saved my bacon this morning! ---
**Author:** ![zach](https://forum.pritunl.com/user_avatar/forum.pritunl.com/zach/32/1105_2.png) [@zach](https://forum.pritunl.com/u/zach)\ **Post date:** [February 22, 2025, 2:17pm UTC](https://forum.pritunl.com/t/google-sso-attributeerror-module-openssl-crypto-has-no-attribute-sign/3057/4 "2025-02-22T14:17:44Z")
The update is currently on the [**unstable repository**](https://docs.pritunl.com/docs/repo#unstable-repositories) and should be in the stable repository in about 30 minutes.