I think you can make LWP::UserAgent tell you in more detail about where things went wrong.
You could run analyze-ssl.pl to find out where the connection fails, or you could look at the response body of the 500 error to see what the X-whatever headers say about the error reason. You could also look at IO::Socket::SSL and turn up the debugging options there to see where things break down.
In reply to Re^3: LWP::UserAgent certificate verify failed
by Corion
in thread LWP::UserAgent certificate verify failed
by cormanaz
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