Google Hates Me
I feel like Julian Assange.
Beknownst to me, sending from Mail.app also sends through the gmail server that is set up on that application. Unbeknownst to me, Google counts all those redirects as mail sent out. And with more than 100 of them, it counts them as spam.
It took me a while to realize it because i was also in the middle of switching my Mail.app/Gmail link from an POP configuration to an IMAP configuration. Therefore, when I went to send an email to a buddy of mine, and I got a stmp error, I assumed I screwed up the configuration. I tried over and over again, different things, rebooting, restarting the app, etc. Finally, i thought I would call it a day and just go to gmail proper to send said buddy a quick email as to why I haven't responded in a timely manner. That's when i saw this:
In an effort to fight spam and prevent abuse, Google will temporarily disable your account if you send messages to more than 500 recipients or if you send a large number of undeliverable messages. If you use a POP or IMAP client (Microsoft Outlook or Apple Mail, e.g.), you may only send a message to 100 people at a time.

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