One more thing though -- <something@gmail.com.com> is not technically an invalid email. It may be a nonexistent mailbox but there's nothing malformed about it: gmail.com.com is a valid domain and it has an MX record, so it could receive mail. In fact as @David M suggests it's a prime candidate for just swallowing all mail sent to it, rather than bouncing, leaving mysteries in its wake.
So while a human can intuit that "example.com.com" was probably meant to be "example.com" (or was it meant to be "example.com.au"... hmm) a machine can't figure this out autonomously. However, as @Josh points out, if the machine tries to send to something@example.com.com and it Hard Bounces, that gives the feedback needed to at least look into it.