Hello all, I'm having a problem with Apple Mail that's been troubling me intermittently for quite a while. Often when sending an email from my domain name email account, Mail will report that it was unable to send and suggests that I select a different SMTP server from a list of my other email accounts. After trying with the same server a few times, I usually give up and send using my Hotmail server (this is annoying, as sometimes it tells the recipient that it's sent from my Hotmail account, sometimes not). The main issue is that I usually find out later that every email has actually sent, and the recipient now has three or four copies of the email in their account, despite Mail reporting that it was unable to send. I'm sure that my mail settings are correct, as this is an intermittent problem - sometimes there is no issue at all. It seems to occur more often if I'm sending an attachment with the message (although that might not be the case). I've yet to notice whether this occurs on other devices, but I will try to make it happen on my other laptop and phone. Obviously my main issue is that I have no way of telling whether my email has actually sent or not. Also I look like a massive noob when someone receives fifty identical emails from me, which is pretty unprofessional. I guess I could automatically Bcc myself in on every email I send, but obviously that wouldn't be overly practical. I'm running OS X 10.5.8 on a Macbook, and Mail version 3.6 (936). I would attach a screenshot of the message, but obviously now that I actually want the error to happen, it won't. If you need any more info I'd be happy to provide. I'd be really grateful to anyone who might be able to help with this. Edit: It's just happened again and managed to get a screenshot. Just to clarify, I'm not trying to send using my hotmail account, it's a personal domain that I've blurred for security. I can confirm that despite receiving the error message, I Bcc'ed the email to myself and it is in fact in my inbox.