Q: How can I enable "automatically bcc myself" for a certain account?

Mail > Preferences > Accounts. Choose the Account you want Bcc set too. Then, under the Composing setting, enable Automatically Bcc myself.

When you are composing an email. there is also a setting drop down adjacent to From: that allows you to dynamically allow the Bcc field.

Mike,

I thought differently and now I see what you mean. Nuts. Mail rules only work on inbound messages.

That leaves enabling the Bcc field per the above graphic, and manually entering the initial letters for your email account that you want Bcc to use. The old-fashioned email way.

If you have AppleScript comfort, you may be able to concoct a wrapper application around Mail that provides a Bcc solution with auto-filled Bcc address. I would Google: AppleScript Auto Bcc emails.

Hi I have automatically enabled the Bcc option in the specific account I want however, it doesn't do it. I have to manually type it in every email. Am I missing something?

Thanks.

You might want to consider starting a new discussion. Since this one is a couple of years old, less people are likely to look at it. A new post would be much more visible. You can link to this one.

No, you aren't missing anything. As posted above, that doesn't work.

Thanks I just realised it's two years old. I'll try the AppleScript Auto Bcc emails advice. Thanks again!

You are welcome.