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Also some additional information:
I get the same exact error when I have the initial call as:
my $smtp = Net::SMTP::SSL->new(
Host => "mail.peakpeak.com",
Debug => 1,
Port => '465');
or
my $smtp = Net::SMTP::SSL->new("mail.peakpeak.com",
Debug => 1,
Port => '465');
And I have another perl program on the same machine (In the same directory even) that uses IO::Socket::SSL to make https requests (Via LWP::UserAgent), which works perfectly.
I'm not actually sure this is an issue directly related to IO::Socket::SSL and not Net::SMTP or Net::SMTP::SSL (Although the latter simply substitutes IO::Socket::SSL for IO::Socket::INET in the former)
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