Mail.app rules might be the easiest solution, since you can control them right on your Mac, but they are my least favorite, because they only work once your Mac has had a chance to sync your email, which means that your Mac must be on 24/7. If you want your previously sent emails to appear they must be dragged from Mail's local Sent folder to the Sent folder listed under your account. Not receiving email. Once in a while, your Mail.app (sometimes referred to as 'Apple Mail' or 'Mac Mail'), stops receiving new mail.

In Apple Mail it is possible to send an email message from a different email address than the one associated with the email account you are using to send/receive through. What do I mean by this?

Check out the following examples. For the solution, look further down. Some examples of the problem One example: I use email forwarding addresses a lot. This is an alias address that forwards to a real email address/account. For instance, if I am providing an email address to a web site I don’t necessarily trust with my address (will they sell it to a spam list?) I will provide them with a unique alias or forwarding address. I set up this unique address on my mail server as a forwarder.

For example, sitename@mydomain.com forwards to re alemail@mydomain.com. In this example realemail@mydomain.com is my real email address, and sitename@ is the name of the site I am giving an email address to, such as during an account registration process. This way if I ever receive spam to this forwarding address I will know exactly where the address was leaked from.

But here is the issue: What if I later need to send someone (the site owner, for instance) an email from sitename@mydomain.com? With Apple Mail there is no obvious way to do this. Another example: I use a Gmail account to consolidate emails from a number of other accounts I have.

Gmail checks these accounts for me. Gmail even lets me send out messages as though the message originates from one of these accounts.

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It works well. Gmail has great spam filters so I find it useful to run all my email accounts through Gmail. Apple Mail has fairly good IMAP support and allows me to access my Gmail account over IMAP. This works well enough and this is how I access my Gmail account. But what happens when I receive a message that was sent to one of the accounts Gmail is checking for me?

If I hit reply in Apple Mail, there is no way to send the reply FROM the account that originally received the message. I recently had this problem with Paypal.

I’d sent them a message from my Paypal account using the Email Us form on their web site. Their reply came in by email to a Gmail account that consolidates emails for me. I replied in Apple Mail but then got told by Paypal that they could not correspond with me because the message I sent them did not come from an address not associated with my Paypal account. I had to log into Gmail in order to reply because there was no obvious way to do it in Apple Mail. The Solution It turns out that Apple Mail has an easy way to resolve this problem, but it is not at all obvious and not explained anywhere in Mail Help (not as far as I could see). Go to Preferences > Accounts. Looking at the “ Account Information” section there is the field “ Email Address:“.