If your are having problem with Outlook 2010 through exchange server and using cached mode you may try this one.
This help me solved one of our case.
Close Outlook.
Run Regedit.exe
Check if you have this registry key.
HKCU\Software\Microsoft\Office\12.0\Outlook\Cached Mode
If not, create that key.
Add a new DWORD value inside, name it SendOne.
Set the value to 0.
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