ICloud account cannot send mail from Apple Mail Big Sur

I am at the end of my rope trying to solve this problem. I have been trying to work with Apple Support on this issue since mid-July and continue to bounce in their system and have yet to get help fixing it.

I am using a 15 inch MacBook Pro 2018 with 32GB RAM and 1TB SSD drive running macOS 11.6 (latest version). I use Apple Mail with a combination of email accounts including Gmail, 3rd party email, Microsoft Exchange and iCloud.

I sent the computer to have its battery replaced in June (and Apple also replaced a problematic butterfly keyboard at the same time). While he was away for service, I used a replacement MacBook Pro that I logged into my iCloud account to keep things synced for me while I worked on the loaner machine. When I recovered my computer, I signed out of my iCloud account on the loaned Mac and erased its hard drive, returning it to its factory settings. I then reconnected my MacBook Pro to iCloud and the problems started.

I reconnected to my iCloud account and everything worked except sending mail from my iCloud account in Apple Mail (I get iCloud emails with no problem). If I try to send an email from my iCloud account in Apple Mail (it doesn’t matter the size of the email or whether it has attachments or not), the mail tries to be sent for about 10 minutes and then I got errors, saying it can’t reach the SMTP server and ask me to choose another mail SMTP server. This happens regardless of which network my MacBook Pro is connected to (wireless or Ethernet). My iCloud account works fine through the web browser on my Mac and on my iPhone and iPad.

Apple Support asked me to remove and re-add iCloud SMTP server (no fix), reinstall macOS (no change), then create videos and screenshots of my Apple Mail program to send to their engineering team. In the midst of it all, I kept getting transferred between members of the Apple Support team who repeated each of these actions multiple times to no avail. Finally, they asked me to make sure the latest version of Big Sur was installed (which I did) and try to send again (and it still won’t send mail from my account iCloud).

Connection Doctor shows that the SMTP server for iCloud never terminates its connection and therefore does not work (it just shows the spinning circle).

I have other SMTP servers that show they are not connecting (but they are not stalling like iCloud connection).

Does anyone have any ideas on how I can fix this? I wrote to Apple Support twice last week to reopen the case and they didn’t respond. I need to fix my iCloud mail so that I can send from it on the Mac.

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Steven L. Nielsen

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