Use an alternative e-mail address after repeated failed attempts to send.

Question

My company uses a small e-mail server company that offers a lot of benefits, but occasionally goes down for a day or two. I would like to find a way to automatically use another e-mail address after several failed attempts to use this server.
Thus, if everything is working right, my e-mail will use the regular server. However, if the original server is down, when my e-mail fails to send repeatedly using that server, I would like it to default to another server. Is there a way to configure this?
Thank you.

Answer 1

No, you can’t. .Mac’s SMTP server simply doesn’t allow sending from a non-.Mac address.
Doesn’t your ISP include some POP or IMAP mail accounts with access to an SMTP server as part of the service? Such an SMTP server might be less restrictive.
A Gmail account would allow you to use Gmail’s SMTP server. Instructions for setting up a Gmail account are provided here:
http://mail.google.com/support/bin/answer.py?answer=13275
After setting up the Gmail account in Mail and checking that it works, you can use Gmail's SMTP server to send from your other mail accounts as well:
1. Log into your Gmail account on the web.
2. Go to Settings > Accounts.
3. Enable the addresses you want to be able to send from, and let Gmail validate them by verifying that you do indeed own them.
4. For each mail account you want to send from using Gmail’s SMTP server, in Mail go to Preferences > Accounts, and choose Gmail’s SMTP server from the Outgoing Mail Server (SMTP) popup menu.
BTW, if you’re using Mac OS X 10.3 (Panther), as your profile indicates, it would have been more appropriate to discuss this in the Mail & Address Book - Mac OS X 10.3 & earlier forum. If the discussion applies to both Mail 1.x and Mail 2.x, it doesn’t really matter, but it’s difficult to know that in advance.