Re-implementing HTTP over proxy using a raw SSL socket seems like a lot of work. (personally I would try to get the service to use SSH tunneling, but maybe you don't have control over that)

I would guess someone already did HTTP proxy in Perl before, and a little googling proved fruitful:

Stack Overflow: Perl HTTPS over proxy using LWP::UserAgent

Does that do what you need?

In reply to Re^2: IO::Socket::SSL with http proxy tunnel? by NERDVANA
in thread IO::Socket::SSL with http proxy tunnel? by lembark

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