This issue has to do with the behavior of Outlook after waking from Windows sleep mode. Since it only started happening in the last month, I'm guessing that a change has been made in Outlook that causes it to act poorly when automatic send/receives are scheduled during sleep mode.
I'm using Outlook 2016 on Windows 11. I use my laptop like a desktop computer, so I have an external keyboard, monitor, mouse, and speakers. Ever since I bought it, I've had a problem with Windows 11 not sleeping automatically. (If I disconnect the external keyboard, it does sleep automatically, so that issue is understood, although not resolved.) Therefore, I usually sleep the laptop manually, in order to save my monitor. If I just let Outlook and Windows run, without putting the computer into sleep mode, the problem I'm about to describe doesn't occur.
I have three IMAP email accounts, all through AOL. When I click Send/Receive after waking the computer from sleep mode, Outlook successfully does sends on all three accounts, and receives on two of the three, but then hangs without receiving the emails from the third account.
If I switch to a different email account, this triggers a synchronization. If I then switch back to the problem account, there is usually no synchronization. If I manage to initiate the synchronization, it never completes.
However, if I then restart Outlook and do another Send/Receive, sends and receives work for all three accounts.
This means that every time I want to check for emails from my third email account, I have to first restart Outlook. However, if I don't manually sleep the computer, which means my external monitor is always on, then the regular send/receive cycle functions correctly.
Although I may have noticed this issue on very rare occasions over the last year or so, it didn't start happening consistently until August 29, 2025. Now it happens almost every time.