If delivery to mailboxes on the mail server (smtp.officedomain.com) is successful, then you probably don't have server authentication issues. More likely is that the SMTP interface at smtp.officedomain.com is configured to accept email to local accounts and to refuse to relay email to other mail servers.

You should check $Mail::Sendmail::error and $Mail::Sendmail::log after sending:

sendmail (%mail) or die "sendmail failure sending to $mail{To}: $!\n\$
+Mail::Sendmail::error: $Mail::Sendmail::error\n\$Mail::Sendmail::log:
+ $Mail::Sendmail::log\n";
[download]

That should give you some idea of what happened. You could also check the logs on smtp.officedomain.com to see what it did with your email. It probably logged that it refused to relay, when you send to an external address.

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