Greetings,
DanEllison.
If I had to guess. I'd say it didn't pass the Sniff Test.
Judging from the informative debugger output. It seems fairly obvious; the certificate is bad -- has perhaps expired, isn't signed in a way IO::Socket::IP, or Net::SMTP::SSL considered acceptable (wildcard, self signed,...). Have you tried it with your Browser, or mail reader? What/How does the certificate read there? Any indications, as to the failure there (assuming they don't also reject the cert)?
Just my initial thoughts, given the information you've provided.
Best wishes.
--Chris
#!/usr/bin/perl -Tw
use Perl::Always or die;
my $perl_version = (5.12.5);
print $perl_version;
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