Message Redirect: MacOS Mail 14.0 (Big Sur) Not Allowing Redirect Message Function

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Level 1

19 points

Message Redirect: MacOS Mail 14.0 (Big Sur) Not Allowing Redirect Message Function

This is a pre-Big Sur issue, but I am not able to send redirects using Mail and the Redirect Function under the 'Message' menu. Changing SMTP servers does nothing. Here's my error:

Sending the message content to the server failed. The server response was: From address is not one of your addresses Select a different outgoing mail server from the list below or click Try Later to leave the message in your Outbox until it can be […]

Help!

MacBook Pro

Posted on Oct 6, 2021 5:51 PM

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Answer 1

jdo_apple

Community Specialist

Oct 7, 2021 2:53 PM in response to MacMyDays

Thanks for replying, MacMyDays, and that additional info, it really helps! Next, try running First Aid on your hard drive with the built in Disk Utility tool, as this can correct simple issues like you're experiencing.

How to repair a Mac disk with Disk Utility

To help isolate this further, use safe mode to start up your Mac as it does the following things:

Verifies your startup disk and attempts to repair directory issues, if needed
Loads only required kernel extensions
Prevents Startup Items and Login Items from opening automatically
Disables user-installed fonts
Deletes font caches, kernel cache, and other system cache files

Log in to your user account and test the issue while in safe mode and then restart normally and test the issue again.

How to use safe mode on your Mac

Graphics performance limited in macOS Recovery, safe mode, or Guest User mode

Have a great day and thanks for using the Apple Support Communities!

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Answer 2

jdo_apple

Community Specialist

Oct 7, 2021 12:49 PM in response to MacMyDays

Hello MacMyDays,

Thanks for that info and for choosing the Apple Support Communities. If we understand correctly, you are unable to redirect an email in the Mail app on your Mac. Looking at this Apple resource, this could be expected behavior if an Exchange account is involved:

Reply to, forward, or redirect emails in Mail on Mac

Cheers!

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Answer 3

jdo_apple

Community Specialist

Oct 13, 2021 7:11 AM in response to MacMyDays

We appreciate you trying those steps, MacMyDays. Since you are still having this issue after trying all those steps, please contact Apple directly for further assistance.

Get Support

Cheers!

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Answer 4

MacMyDays Author

Level 1

19 points

Oct 7, 2021 2:40 PM in response to jdo_apple

Thanks jdo!

Yeah, I read that tech note before posting my experience. I've reproduced this issue with another iCloud account: trying a redirect on a message from my brother's iCloud account—same result:

CANNOT SEND MESSAGE USING THE SERVER ICLOUD

Sending the message content to the server failed.

The server response was: From address is not one of your addresses

Select a different outgoing mail server from the list below or click Try Later to leave the message in your Outbox until it can be sent.

Sending from: (null)

Seems to be some other problem here. Any other thoughts? Have you tried it successfully?

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Answer 5

MacMyDays Author

Level 1

19 points

Oct 12, 2021 4:41 PM in response to jdo_apple

Hey jdo —

Thanks. I did as you suggest but still get the same behavior. I don't think this is a hardware issue. It seems to be an authentication issue. It's maddening, to say the least.

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Answer 6

MacMyDays Author

Level 1

19 points

Oct 12, 2021 4:52 PM in response to jdo_apple

Oh, it should be noted that I created a new user on my MacBook Pro. I tested the redirect function with the new user set up (my Apple ID) and even on the new user I get the same error message.

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Message Redirect: MacOS Mail 14.0 (Big Sur) Not Allowing Redirect Message Function

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