I had this same problem with my Droid and Google Apps acct. With increasing frequency, emails would build up in my outbox -- only when replying to emails, not composing a new message. Trying to push them out ("send outgoing messages") would result in a "connection error" even though the server / port / security settings were all correct. Sometimes these efforts would fix the problem:
-- power down and back up
-- uninstall / reinstall battery
-- clear history
-- uninstall / reinstall email accounts
-- perform master wipe of the device / restore factory defaults / reinstall accounts
Then the problem would start again. First Verizon told me that my password was probably incorrect (are you kidding me?) and ultimately they said it must be a software problem and sent me a new (refurbished) phone. Same problem. Then VZW tech support told me that my Droid was probably NOT COMPATIBLE WITH GOOGLE APPS (seriously???) and I should try another email client. Motorola rep DID NOT KNOW WHAT GOOGLE APPS WAS and told me to either install a 3rd party email pusher like K9 (shouldn't my Google account work on a Google device without a 3rd party app?) or to BUY A BLACKBERRY INSTEAD. I am not making this up.
Today I tried the suggestion to enable "require sign in" under "outgoing server settings". As soon as I did, my outbox cleared. Let's see how long this fix lasts!
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