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Certificate Errors on Websites

Hi all, for the past few months we have been having issues with several certificates on random websites. The end user basically sees a message saying that the site is insecure and asks them if they want to continue. It seems that if we bypass the Sophos Web Appliance fully it seems to work correctly, and once it has worked correctly once on a PC, it seems to continue working from that point onwards, regardless of user.

We do not use HTTPS packet inspection, but we do have the Sophos Certificate pushed to all clients which is in date.

Websites doing this at the moment for example are https://gov.uk and also https://icloud.com has been doing it too.

Has anyone experienced issues like this? Is there anything I can do with the Web Appliance to narrow down more what is happening here?

Thanks very much. 



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