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AnyConnect Mac OS no valid certificates available for authentication

codingjesterr
Level 1
Level 1

Hey guys, I'm trying to configure AnyConnect client on my MacOS Monterey. I'm using certificates (issued by my Enterprise Root CA running AD Certificate Services) to authenticate my clients.Everything went as planned,I connected to the vpn and worked for few days but one day Anyconnect dropped the connection  and showed "no valid certificates available for authentication".

 

Certs are  exported from my root certificate and user certificate from my Windows machine (which is able to authenticate successfully) and imported those certificates onto my Mac. The root certificate shows up as "Trusted" and the user certificate status reads "This certificate is valid". Both are being stored in my "login" keychain.

I've done it multiple times as a Helpdesk specialist and most of the time its just works but in some cases problem accure as mentioned.Workounds that seemed to help were:

Reinstalling vpn
Generating new certs even though the old ones are the same(valid,expiration date is fine,and  stored in correct Key chain)
changing to certs to untrusted

None of theme helped in that case.

Could you provide me any solution to this or how can I analize the logs that will led me to the problem that Anyconnect faces?

 

I'm curious if thats the problem with MacOS or the VPN or cert by itself.

Thanks.




 

That's it.

 

Any thoughts?

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