Mail messages will not send and remain in Outbox

I have a POP using Gmail and it has usually worked extremely well.
Recently I have had a lot of problems with messages I am sending
getting stuck even though the connection doctor indicates not problem.
Error message will sometimes say could not connect to server.
I have restarted etc. and the only way I can get my messages out of the
Outbox is to quit Mail and re-open and then they will go out without
any problem.
Any ideas how to fix this problem permanently??
Thanks!
Zentor

Go to Apple Menu > System Preferences > Network, choose Network Port Configurations from the Show popup menu, and make sure that the configuration used to connect to Internet appears at the top of the list. Leave checked (enabled) only the port configuration needed to connect to Internet and Built-in Ethernet (in that order if not the same), uncheck (disable) the rest of network port configurations and see whether that helps — if it doesn’t, turn ON again the ones you want enabled.
Mail keeps information about outgoing (SMTP) servers in a separate list independently of the mail accounts themselves. The account settings just associate one of the available outgoing servers with each account. Orphaned or dangling outgoing server entries (i.e. not associated with any account) sometimes cause weird sending problems. Go to Mail > Preferences > Accounts > Account Information > Outgoing Mail Server (SMTP), choose Edit Server List from the popup menu, and delete any servers that shouldn’t be there. The Edit Server List panel shows the account each outgoing server is associated with.
If the problem persists and you have more than one mail account, try moving the account that has the problem to the top of the list in Preferences > Accounts.

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