My Outlook prompts for password every time it comes back from sleep or started

I've Microsot Outlook for MAC 2011, version 14.4.1 installed on my MAC Book Pro Retina Display with OS X Version 10.9.2 and everytime my outlook comes back from sleep or is started or there is a little fluctuation in Wifi signals, prompts me for my email password. I checked the option of save my passord, deleted all previous passwords from Keychain but it doesn't works, so please help. My email at my official domain (not free domains) address is configured perfectly and my send and received is working fine.

I have that problem in Outlook, too. When I get the Yes/No dialog box, I simply click "No" and my machine continues to receive mail.
It's most certainly a pain, but coming out of sleep, your network doesn't kick in for a minute or two. I don't think that it's really a bug in either OS X or Outlook: it just takes that minute or so for the network to wake up.
Clinton

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