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So is this problem persistent/impossible to fix? Or maybe some OPNsense guru have some kind of a workaround/solution for this?

That will be my last resort. The problem is that i am new here and the previous IT guy had no regard for software standards... For now there are many computers with diffrent systems, W7, W8, W8.1 and W10. Aside from that Office 2010, 13 and 16. Add to that W2016 server and we are looking at more than 200GB of data just for WSUS server. For now i dont have that kind of space and no spare Windows Server licenses :(

Hello, i am facing the same issue. Can't use windows updates with SSL Proxy enables. I have imported the generated certificate onto the machine and websites work correctly. My cert is being recognized and everything works except Windows Updates. Im geetting an error (0x0801901f7). Seems like its a problem with certificate? I have added all windows updates domains into SSL no bump list. Its very problematic for me as i need to use Transparent proxy to block porn sites in my EDU organization... :(