Apple Mail always chooses a server that doesn’t work for the mail address I have as From. I have to wait for it to time out, then choose the right one. I absolutely cannot find a way to reorder these SMTP servers or make it use the SMTP server listed in the account for that email. The preferred email is wunder@wunderwood.org, but it uses the GMail one every time.
I am so tired of waiting two minutes after sending each email. Plus, there is a race condition between successfully sending it and getting the “not sent” notification, so I send two copies half the time.
I’m actually fairly knowledgeable about mail protocols, I even configured Sendmail back in the day.
Does the email address have a separate “account” associated with it, or can you set it up that way? In the mail settings, on the “Accounts” tab, when I select an account on the left and look at the “Server Settings” panel on the right, I can set the specific SMTP server associated with that account.
Yes, these are all separate accounts. It is weird that when I send from wunderwood.org it tries to send it via GMail. That just seems broken. Send to the SMTP server associated with the account I’m using, right?
I’d even be OK with changing the order of the accounts.
All pretty standard. Account is enabled and online. Server settings were set up with a config from Fastmail (my mail provider).
Hmm, the gmail account doesn’t have server settings, it has a drop-down for “Outgoing mail account”.
The account that works isn’t even enabled.
Things are more complicated because I tried the Google group email account, then it wasn’t even good enough, so I moved everything to Fastmail. But there is no way to back convert the account to a normal Gmail account because Google doesn’t actually build products.
I have a similar issue but not quite the same. I don’t get a failed delivery message, it just sends from the wrong account.
I have three primary email accounts; iCloud, gmail and Exchange. When I reply to an email sent to my iCloud account, Mail ALWAYS chooses the gmail account to reply with. Annoyingly, this is a shared account I use with a friend so if I don’t catch it my personal emails end up entwined with my shared account.
I’m yet to find a way to resolve it but it’s incredibly frustrating. There’s probably a case where replying from a different account is desired but I’m yet to think of one.
Autofill is different, though I have had to clean up previous recipients. I copied an email from a document and MS Word had “fixed” the dashes in the domain name to be Unicode hyphens. That was a mess.
Did you check under Mail Settings > Composing > Send new messages from:
You should be able to select a permanent outgoing SMTP server or pick the automatic setting, where Mail tries to remember which SMTP server you used before with this particular recipient.
It’s also slightly ambiguously labeled “Send NEW Messages” which suggests it may be ignored for replies. I have a vague recollection of a setting in the past for a Reply With address but it doesn’t seem to exist now.
I’ve been caught out again and this time it was private banking information. For goodness sake Apple, get your mail app to reply from the email address to which the email was received. Surely it can’t be that hard.
I’ve done the only thing I can to resolve it - turned off my other email accounts. This is hardly a reasonable action for a fundamental app from a multi-trillion dollar company. Instead of putting questionable AI into email, how about making it work the way it should?
[apologies if I’m repeating what was already said…]
I’m afraid the short answer is: macOS Mail doesn’t work that way.
Your SMTP server list isn’t a list of “all the servers Mail could pick from”. It is a list of all SMTP servers you’ve set up, and it is the same list across all accounts. Each account is only sending to one server. Notice the “In Use By Account” column in the server list; it is showing which account(s) are currently using that server.
What you want is some way to assign multiple servers to one account, and then either have a place to put rules for which one to use, or for Mail to intelligently pick the server.
But “intelligently” picking is harder than it seems. Sure, it seems like sending from an @wunderwood.com email address should use a wunderood server. But imagine you’re writing an email client for Linux. How would it intelligently know that @Mac, @me, and @iCloud emails addresses should all be sent via iCloud, but @msn.com, @live.com, @hotmail.com, and @outlook.com all go through the Outlook SMTP server?
And, note that every change breaks someone’s workflow. I happen to want my mail from @iCloud.com to go through my Fastmail.com SMTP server, not iCloud, even though iCloud is in my SMTP server list. (That’s so that all my mail lands in my one FastMail Sent Mail folder.) So if Mail worked the way you wanted, it would break my workflow!
Note: How can I send mail @Mac.com through Fastmail? It works because I’ve configured Fastmail to know that any mail I send it From: @Mac.com, should be forwarded to go out through the iCloud SMTP server.
