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Help Can't send email

What is the deal with this phone...my buddy at the office has a SF and it will not send his email, it just sits in the outbox forever. I thought that 2.2 would fix this problem but how long can one wait. I have the DX and I have never had any problems with the same exchange email account...

The phone receives email just fine...any ideas
 
He must have a setting wrong. I have 5 email addresses, mixture of exchange, imap and pop. No issues with any of them.
 
What is the deal with this phone...my buddy at the office has a SF and it will not send his email, it just sits in the outbox forever. I thought that 2.2 would fix this problem but how long can one wait. I have the DX and I have never had any problems with the same exchange email account...

The phone receives email just fine...any ideas

I have saw this a time or two on mine I just look after pushing send if it doesn't send right away I push refresh and it goes
 
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