Outlook sporadically stops checking mail I use Outlook 2011 (14.4.3) to connect to my organization's exchange server from my Mac (OS 10.9). Normally I receive mail shortly after it was sent, but on occasion Outlook will refuse to check my mail for periods ranging from minutes to hours. 

By "refuse to check my mail" I mean that:


When I click the "send/receive" button, the button responds with a click animation, but it does not check my mail.
If I open the "progress" window (cmd-7) I can confirm that no activity is shown. 
No error messages appear in the "errors" window (cmd-8). 


During these times:


I can log in to webmail and confirm that there are messages that haven't been downloaded. 
My mac has full connectivity otherwise
Outlook is able to send emails, which are received by others right away (but my sent mail box isn't updated either). 
The status message in the lower-right still says "connected to [account name]" and accurately displays the last time it connected to the server. 


The problem sometimes resolves spontaneously, and I'll get a bunch of old mail at once.

Quitting and restarting usually fixes the problem. But that requires me to notice that it's happening, which sometimes doesn't happen for several hours, during which I can miss emails that required an immediate response. 

Does anyone have any suggestions or diagnostic steps?
I have experienced the same issue with Apple Mail since updating to Mavericks.  I was hoping Outlook would be better, but it sounds like it has the same problem.

My understanding is that this occurs occasionally when checking mail hosted via Kerio or Exchange.  My workaround is to use Thunderbird, which has not had the problem.  I actually have Thunderbird running simultaneously just for the alerts, and if there is an alert but Mail hasn't received new mail, I know to quit and restart.