These last couple of days I have been experiencing a quite frustrating behavior of what I think is a problem with Apple’s Mail Client.
The symptoms are simple. All email sent from a dotMac account to a gmail account is sent to the spam folder by google’s filters straight away. After some tests and some initial swear words to google’s filters, I’m starting to think that the problem might well be a poor/defective mail software by apple.
1) Sending the email to several recipients seems to solve the problem (at least if one of them is CC’ed)
2) Sending the email from the Mobile Me web interface also seems to work alright
3) Aliases feature the exact same behavior
It seems there’s some buggy behavior somewhere in the client or in the mail delivery infrastructure which is causing perfectly valid messages to be considered spam. Maybe some faulty header field, perhaps a DNS problem with the STMP server…
Meanwhile, remember to CC somebody (I normally do myself) to get your messages properly received!!
Update: Things seem to be back to normal again. All my messages being properly received. Still, I’m getting comments of people still finding troubles. A trick that was working fine for me in the meantime was using the @me.com extension to send the emails. Try this and comment back on the results!