I have a one client with multiple users that are having trouble using Outlook Anywhere in Outlook 2013. The problem is that Outlook takes a very long time to connect (rarely connects) to the exchange server and the connection will eventually drop.
1. This issue is occurring on multiple laptops all running Windows 7 pro and Outlook 2013.
2. This issue happens every time they try to use Outlook on a South West flight with their "in flight" Wi-Fi. This issue also happens using some hotel Wi-Fi's
3. Average ping from a South West flight to the exchange server is ~700ms, ranging anywhere from 600ms-1400ms with 0 dropped packets.
4. Running testconnectivity.microsoft.com from the South West flight comes back all good.
5. Sending email from a client's iPhone using the data plan works.
6. Sending email form a client's iPhone using South West Wi-Fi works.
7. OWA works using South West Wi-Fi, slowly.
8. Outlook has no issues staying connected at their office or the user's home Wi-Fi (exchange server is located in a datacenter within the same state).
9. There is not a VPN in use.
What could cause Outlook to take so long connecting to the exchange server and eventually drop the connection? Any ideas why an iPhone and OWA work on South West Wi-Fi but Outlook doesn't? My client would like to use Outlook and not have to bother with OWA.