Mail still changes the From: account when I enter a To: address

I have several email accounts and use Apple Mail for all of them. For example, If I select my .mac email address in the sidebar, and enter a name I email from multiple accounts, mail changes my From account to another account. I frequently email several people from different accounts and this is annoying. I see that someone recommended “Automatically select best account” but that doesn’t help.

Any recommendations? Other than changing to a new mail client? I miss Eudora, how old am I?

I’m not sure what you mean when you say “If I select my .mac email address in the sidebar.” Which sidebar?

I don’t know if this answers your question. I have different accounts, and want to select which account I reply from. I set Mail > Preferences > Composing “Send new messages from:” to the account I most often use. No matter who I reply to, it sends from that account. If I want a different FROM address, I change it in the newly composed message before sending.

I have quite a large number of email accounts that I now route through Apple Mail, as you do. The sidebar list can be very long, as I have lifted most of the Inboxes as “Favorites” to the top of the list.

Under Sonoma, when I select one of those Inboxes and then start a new message, Mail opens a new compose window with that account as the “From:” account—the behavior you’re expecting. I tested this several ways (including highlighting the Trash box before composing a new message!) and it worked as expected every time.

“Automatically select best account” is a programmatic way of saying “Don’t compose all new messages from the same account”…some folks would want to send all their messages from one account.

I’m wondering if the Mail preferences on your Mac are corrupted.

In the Mail app side bar where it lists email accounts.

I probably have a different workflow. I rarely keep that sidebar of accounts and mailboxes open. My mail comes in to a unified Inbox. From there I reply; the reply always comes from my preferred account unless I change it in the new message (the “from:” popup in the new message window, below the Subject header).

I do have a few rules to file incoming messages into a few folders. They are in the bar directly below the tool bar in the main Mail window. I click on one of those folders in that bar (still not opening the sidebar), select the message, and reply. And the same process takes place: reply by default is from my preferred reply address, unless I change it.

But like I say, this works for my workflow. I used to set preferences to “Automatically select best account” for replies, but I didn’t like that. I want to be able to specify myself which account is used for the reply.