Office 365 mail stuck in OUTBOX

Hi,
We recently upgraded our Exchange Environment to Office 365. Suddenly my users started complaining e-mails would be stuck in OUTBOX. It would say sending but the bar would load forever. The only way to stop this is to restart OUTLOOK and then the mails would
be sent. All the new emails would be received too.
On the web I found out that people that were using a DLINK router had to turn off SPI. We were using a DLINK router too but we didn't have the SPI turned on. But to be sure I swapped the DLINK with a Cisco. The problem still persists.
http://community.spiceworks.com/topic/382519-outlook-stuck-on-outbox-if-left-idle
I also deleted some users' OST file and would reload it to see if this would improve the situation. Also this didn't help.
All my users surf via a squid proxy server. I don't and I never had the problem, so I changed my settings so I would surf via the squid proxy server and I also experienced the problem. I found this article on technet.
http://blogs.technet.com/b/onthewire/archive/2014/03/04/network-perimeter-tcp-idle-session-settings-for-office-365.aspx
I was wondering if there are other sysadmins out there who experienced the same problem with using Office 365 and squid. Do you have any solution for it? Because I haven't found one yet.
Kind regards,
Michael

Hi Mike,
How about sending emails to external via OWA on your laptop and desktop?
If working well in OWA, it seems an issue on the Outlook 2013 client side.
Please try to run Outlook under the safe mode to avoid some AVs and add-ins.
Please try to re-create profile to refresh the caches.
If not working in OWA, since Exchange 2013 is different from Office 365, I suggest ask Office 365 forum for help so that we can get more professional suggestions.
For your convenience:
http://community.office365.com/en-us/default.aspx
Also suggest collecting detailed error from App log.
Thanks
Mavis
Mavis Huang
TechNet Community Support

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