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    <p>Checking the dependency tree: <code>Email::Sender::Transport::SMTP::TLS</code> ==> <code>Net::SMTP::TLS::ButMaintained</code> ==> <code>IO::Socket::SSL</code> ==> <code>Net::SSLeay</code></p> <p>Both <code>IO::Socket::SSL</code> and <code>Net::SSLeay</code> supporting the X.509 client certificates. So <code>Net::SMTP::TLS::ButMaintained</code> and <code>Email::Sender::Transport::SMTP::TLS</code> should be enhanced to support client certificates. A proper way should update both modules to allow the <code>SSL_key|SSL_key_file</code> and <code>SSL_cert|SSL_cert_file</code> parameters. </p> <p>Here is a quick dirty one -- you need to create modified <code>Net::SMTP::TLS::ButMaintained</code> and keep it locally. </p> <pre><code># modify the Net::SMTP::TLS::ButMaintained; # built a private version which have client certificates sub starttls { my $me = shift; $me-&gt;_command("STARTTLS"); my ( $num, $txt ) = $me-&gt;_response(); if ( not $num == 220 ) { croak "Invalid response for STARTTLS: $num $txt\n"; } if ( not IO::Socket::SSL::socket_to_SSL( $me-&gt;{sock}, SSL_version =&gt; "SSLv3 TLSv1", ### private changes begin: append following two lines. SSL_use_cert =&gt; 1, SSL_cert_file =&gt; "path_to/your/certificate_file.pem", SSL_key_file =&gt; "path_to/your/private_key_file.pem" ### private changes end: ) ) { croak "Couldn't start TLS: " . IO::Socket::SSL::errstr . "\n"; } $me-&gt;hello(); } </code></pre> <p>Please leave the User and Password parameter as blank. </p> <p><em>Good luck!</em></p>
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    1. COThanks!! Thats really useful. Will keep this question updated to reflect the implementation
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      1. USYa. Perelman
 

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