Hey, So Apple Mail has been driving me crazy lately. It's such a shame because it's such a slick program, but it looks like a couple of the problems I experience are not just problems for me but many users. For instance, accounts using SSL constantly asking for the password, often 4-5 times within a thirty second window. One issue in particular has become too workflow crippling though. I have six email accounts in Mail, all POP3 (I need access to emails when I'm away from WiFi as well). My work email is set up to use my workplace's SMTP server, which belongs to the ISP of the office. Obviously, this means I can't send through this SMTP server when I'm not in the office. When I'm at home I just send through my personal SMTP server -- when I remember to specify that instead fo the office default before I send the email. When I forget, Mail usually won't say a word about its inability to send the email and I'll assume it's gone and continue about my day. In the following 24-48 hours, at some point, Mail will let me know it couldn't send the message. Up to two days later, by which point the lack of communication has already led to multiple problems, only worsening the headache. Mail insists on hiding the outbox 99% of the time, so when it gives up sending an email and doesn't prompt me, I have no way of knowing whatsoever short of calling whoever I emailed to confirm they've received. It's pretty necessary that I use the office's SMTP server when I am in the office, so I can't switch the account over to just one SMTP server.. believe me, I would have done it a long time ago. Short of that, I can't find any other solution. I've been looking more and more into Postbox, but I'm not sure I'm ready to dive right in at the risk of screwing up my local/remote email syncing. Has anybody experienced this? Any suggestions would be greatly appreciated, I'm tired of getting in trouble for failing to send important emails, and my boss is getting tired of the 'Apple Mail is incompetent' excuse.