in reply to Re^2: Net::SMTP::SSL ACK!!
in thread Net::SMTP::SSL ACK!!

This looks for me not like a problem at the SSL level but at the plain socket level, i.e. that the TCP connection to smtp.gmail.com port 465 already fails.

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Re^4: Net::SMTP::SSL ACK!!
by Dandello (Monk) on Jan 30, 2016 at 00:54 UTC
    So I'm still missing some element (or there's something wrong) in
    my $mailer = new Net::SMTP::SSL( $smtp_server, Hello => 'mydomain.com', Port => $port, Debug => 1, layer=> 'ssl', );
    I've gone through the documentation for Net::SMTP::SSL and except for the layer => 'ssl' parameter, everything looks like the examples. Luckily this code isn't mission critical and I can fall back to TLS, but it would be nice to have it work with SSL.

      Try removing the parentheses or using the plain method call syntax Net::SMTP::SSL->new(args). I am uncertain whether a space between Net::SMTP::SSL and its arguments is required in indirect object syntax, but I recall having had similar syntax bugs in my own code.

        I've run a syntax check on it and it checks out okay, syntax-wise.

        I'm now wondering if there's server configuration that's not quite right. If so, it may take me a while to figure it out.