Two times in this week i faced this: Error: An error of type OpenSSL::Digest::DigestError happened, message is Digest initialization failed: initialization error.
It happens when I try to use Metasploit or evil-winrm tools. Please need urgent help if possible.
I have not seen error I don’t think. If you aren’t on our discord, you are welcome to join. I know the frustrations of tools not working when you need them. You might get a faster response there.
From what I recall, this likely has to with ruby generally and a lack of OpenSSL3 support. I do know fixes are finished/being worked on. I’m assuming you are on Kali? I don’t use Kali personally, but apparently running a full upgrade helped out some people. That’s probably what I would try first.