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Sending mail with alternate "reply-to" address

For years I've been able to send mail (Apple Mail app) from my main address ("Rick@..." at my own domain) or choose a "Support @..." variation, but it suddenly stopped sending the emails just a few days ago, without my changing any settings or OS updates. Incoming Support mail still appears, since the server redirects it to the personal mailbox. Mail appears to send the Support emails, but they cannot be found to be displayed -- and I suspect they are not actually being sent. Clicking the little Reply icon does not display the reply I composed, only an alert "Error. Mail was unable to find your reply to the message. You may have deleted the message."


My main account is set up in Apple Mail as POP. Also in Mail, I have had a second account set up as IMAP (otherwise it won't set it up because it sees it as a duplicate of the personal POP version) that sends using the same settings as the main account, the only difference being the "Support@" Reply-to field. It's important to be able to choose my personal address or the Support address when I compose a new email.


Something that now appears different is, under the "All Sent" mailboxes, is that Support's "Sent" mail no longer has the paper airplane icon, but has a blue icon with @ symbol, and under that is the Inbox of my main account.


Maybe this method simply no longer works.


Is it still possible to send using an alternate Reply-to address and have both regular and alternate addresses appear in the From popup menu when composing a new email?


Thank you in advance for any suggestions!

iMac 27″, macOS 11.6

Posted on Jan 1, 2022 2:29 PM

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Posted on Jan 2, 2022 5:53 AM

I have the same OS version on my MacBook Pro as on the iMac, and the same settings work there, so something's likely corrupt in the iMac app. I tried restarting, rebuilding the mailbox (nothing seemed to happen, although there are many many messages there), running Disk Utility to repair the hard drive, but the problem persisted. I could forward from the Support account, change the address to my own when I replied, but still could not simply reply.


Solution: since it's my own domain, I changed the alternate address from a redirect to a new, separate account. It's another password and account to manage, but at least it works again.

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Question marked as Top-ranking reply

Jan 2, 2022 5:53 AM in response to AdobeWanKenobe

I have the same OS version on my MacBook Pro as on the iMac, and the same settings work there, so something's likely corrupt in the iMac app. I tried restarting, rebuilding the mailbox (nothing seemed to happen, although there are many many messages there), running Disk Utility to repair the hard drive, but the problem persisted. I could forward from the Support account, change the address to my own when I replied, but still could not simply reply.


Solution: since it's my own domain, I changed the alternate address from a redirect to a new, separate account. It's another password and account to manage, but at least it works again.

Sending mail with alternate "reply-to" address

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