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Windows SSL Woes

Apologies if this is the wrong section.

I am experiencing an odd issue.

My current setup is Sophos UTM Home, with a third party access point connected. I have managed to successfully set everything I need up, and can access the internet perfectly fine, whether I am connected via WiFi or ethernet. I have tested this on both MacOS and iOS and they both work.

However I have this one Windows device that just won't play nice. It can connect to the network just fine, and can access the webadmin page just fine. But any external website returns an "ERR_SSL_VERSION_OR_CIPHER_MISMATCH" error on chrome and an "Error 1000, DNS Resolution error" on IE and Edge.

I had this error occur on the same device with both PFSense and IPFIRE, which paired with the fact it doesn't occur on any other device, makes me think something is wrong with it. I had initially put it down to a bad network driver or something, but over the week decided to completely re-install windows, and it is currently on a clean install, and the issue is still arising.

Because of this, I decided to bust out an old Windows device and see if it was experiencing the same issue, and it did.

For some reason, I am experiencing an SSL error whenever a Windows device tries to connect to the outside world, does anyone have any ideas? Because this is doing my nut in.



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  • Hi and welcome to the UTM Community!

    Are you using Web Protection?  If so, open the Web Filtering Live Log and paste here about a dozen relevant lines when you try from a Windows device.

    Cheers - Bob

     
    Sophos UTM Community Moderator
    Sophos Certified Architect - UTM
    Sophos Certified Engineer - XG
    Gold Solution Partner since 2005
    MediaSoft, Inc. USA
  • Hi, thank you for your response. Forgot to say, turning on transparent mode completely fixed this issue. I'm not sure why it occurred on the other systems, but that doesn't matter to me now. Thank you for your help regardless.