Same problem here - Windows 7 Pro x64 with Perl 5.14.

Neither Email::Sender::Transport::SMTPS works, nor MIME::Lite with IO::Socket::SSL hack. The problem lies in some module (probably IO::Socket::IP, because Wireshark shows that Perl doesn't send a single packet to the email server and bails with above error.

Previously MIME::Lite+IO::Socket::SSL worked OK.

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Greetings

In reply to Re: Cannot connect to SMTP Server from Windows 8.1 Pro x64 by Anonymous Monk
in thread Cannot connect to SMTP Server from Windows 8.1 Pro x64 by sursan

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