This has been an issue for some time, but lately it's been occurring with increasing regularity. Although I can receive email just fine, there are times when Mail will lose it's mind and not allow me to send. I have an iCloud address and two Gmail addresses set up, and I get this error when trying to send on the Gmail accounts after the computer has been running for a little while.
The message cannot be sent on this account. When I create a new message and send from the iCloud account, it seems to work fine, but I cannot choose the iCloud SMTP server here to send it. I get the same message: Sending from: (null).
When I go to Prefernces / Accounts and then Server Settings, under Outgoing Mail Account I see all three addresses (iCloud + 2 gmail), but when I click on Edit SMTP Server List, I see nothing:
I can Quit Mail, but the problem persists: mail will sit in my Outbox and throw an error. If I restart my entire computer, the messages sitting in the Outbox send and I can use my mail accounts normally for a while. Then it starts rejecting it again. I've tried both turning the Gmail account off and back on in System Preferences / Internet Accounts, and I've tried deleting it entirely and re-adding. I keep having this problem.
Any ideas why?

The message cannot be sent on this account. When I create a new message and send from the iCloud account, it seems to work fine, but I cannot choose the iCloud SMTP server here to send it. I get the same message: Sending from: (null).
When I go to Prefernces / Accounts and then Server Settings, under Outgoing Mail Account I see all three addresses (iCloud + 2 gmail), but when I click on Edit SMTP Server List, I see nothing:

I can Quit Mail, but the problem persists: mail will sit in my Outbox and throw an error. If I restart my entire computer, the messages sitting in the Outbox send and I can use my mail accounts normally for a while. Then it starts rejecting it again. I've tried both turning the Gmail account off and back on in System Preferences / Internet Accounts, and I've tried deleting it entirely and re-adding. I keep having this problem.
Any ideas why?