Last Sunday I sent an important email to fred@example.com (obviously not the real address). I didn't hear anything back and on Wednesday, sent a follow-up message. I still didn't hear anything back.
I then checked my logs, and found the following (formatted for easy viewing):
>
```
mail.log:Nov 1 18:31:09 brevard postfix/smtp[32387]: D9024170C57C:
to=<fred@example.com>,
relay=aspmx.l.google.com[209.85.221.90],
delay=1,
status=sent
…
mail.log:Nov 4 20:24:19 brevard postfix/smtp[13490]: 6FE3E1AA92E9:
to=<fred@example.com>,
relay=aspmx.l.google.com[209.85.221.67],
delay=1,
status=sent
```
Oh no … it's Gmail [1].
We've had issues at The Company with Gmail. Specifically, Gmail seems intent upon classifying all email sent from The Company as spam. And seeing how my website is being hosted by The Company, my guess is Gmail is classifying my emails as spam as well.
I sent a test message to my Gmail account and sure enough, it ended up in the spam folder, with no way of telling why it was sent there, or a way to tell Gmail that I'm not a spammer.
Head, meet desk.
Ow.