Outlook Sending Mail with Gmail.

[Guest]

My outlook using Pop3 with Gmail won't send messages. They remain in my
outbox. When I test my email account all items all items pass (greeen check
mark) and my SMTP requires authentication and is setup correctly.

 

[Brian Tillman]

My outlook using Pop3 with Gmail won't send messages. They remain in
my outbox. When I test my email account all items all items pass
(greeen check mark) and my SMTP requires authentication and is setup
correctly.

Do you scan outgoing mail with an AV program? If so, disable that feature.
Lengthen your server timeout value as well, on the Advanced tab of your
account properties pages. Turn on diagnostic logging to see what
communication occurs between Outlook and the server.