Dot Mac Mail SMTP not accepting attachments over 2mb

So i am trying to help my boss out with sending emails with attachments, but i keep running into the same problem. I can send normal emails just fine, and emails with small attachments work fine (i tried 50bytes, 750kb, 1.1mb, and 1.7mb) but once i get over 2mb i get the error message "An error occured while sending mail. The mail server responded: 4.0.0. Spam filter end message failed [slot2]. Please check the message and try again.". I tried both 2.4mb and 3.2mb files, but no luck. I tried sending with just plain text, and with sending HTML/Plain text. I tried every combination of SMTP server ports i could find, like port 25, no encryption, port 25 TLS is possible, port 25 SSL, port 587 no encryption, port 587 TLS if possible, port 587 SSL, and whatever the default SSL port is (i forget). The computer is one of the newer MacBooks, running BootCamp and windows XP. The mail application is Thunderbird, which i use extensivly on my personal computers. There are no firewalls up, even the router has the laptops IP on DMZ mode, and just to be safe, i made sure i could connect to port 587 with telnet from the command line. Anyone have any ideas? Thanks.

Possibly so, but mobileme is currently having a lot of problems and that might have been reduced to lessen the strain on the servers.

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Hi there.
Since my situation is very similar, rather than start a new thread, I wonder if I could jump on this one for some clarification & to see if I'm okay to proceed with the Tiger instructions you posted.
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Hi there.
Since my situation is very similar, rather than start a new thread, I wonder if I could jump on this one for some clarification & to see if I'm okay to proceed with the Tiger instructions you posted.
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Why? It's not your fault. It's because how Apple Mail stores mail, it simply is not robust enough.
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Dot Mac Mail SMTP not accepting attachments over 2mb

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