Outlook 2013 using Outlook Anywhere disconnects from Exchange 2010

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.
aandoAsked:
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Peter HutchisonSenior Network Systems SpecialistCommented:
In my experience Outlook is very finicky about network connections and can easily drop connections when its far too slow or traffic is inconsistent. Fiddling with the settings will help, and make sure you use the fastest and reliable connection whenever you can otherwise switch to OWA.

This article may explain it more:
http://www.howto-outlook.com/howto/outlookanywherefastslow.htm
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Craig BeckCommented:
Mobile devices don't use a full-blown outlook client, so their experience is less bandwidth-intensive or dependent.  The full-blown Outlook application does a lot behind the scenes, such as authentication to DCs, etc, which means a slow link might not cut it.
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Gareth GudgerSolution ArchitectCommented:
I think this is the key right there.

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).

Hotel connections are notoriously bad. Can't say I've tried the Airplanes WIFI yet. But sounds like it might be time to recommend they test a cellular broadband card/mobile hotspot. At least for the hotels.
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aandoAuthor Commented:
Thanks for all the info. Do you think that setting up Outlook to use a different protocol such as POP and IMAP would make any difference? I don't normally setup exchange in this manner so I'm not sure if there would be an benefit or not.
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Peter HutchisonSenior Network Systems SpecialistCommented:
You can use IMAP but you won't get access to things like Calendar, Journals, Tasks, Contacts or the Global address list.
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Gareth GudgerSolution ArchitectCommented:
Peter is correct. POP and IMAP would be purely mail only.

I would lead towards the Mobile Broadband cards as a backup if the hotel WiFi is bad (or restricted).

Plus some hotspots have time limits during peak usage times. I know some of the Panera Breads will shut off after 30 minutes during the lunch hour.
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aandoAuthor Commented:
When testing via mxtoolbox.com you can go to a place that allows you to "Test Mail server". I put in the mail.domain.com and it comes back with SMTP Server Disconnected. When I click on more info it says, “Connection disconnected prematurely” We were able to connect to your email server on port 25. Your server either disconnected before we sent our final QUIT command or did not respond to one of our other diagnostic commands within 15 seconds. This may be due to a network problem, or could be anti-spam feature of your email system.

Any ideas as to what I can check to see why this is disconnecting before the QUIT command is sent? Could this make the connection drop on slow internet from the Airplanes WiFi?
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Gareth GudgerSolution ArchitectCommented:
Doubtful. Sounds like that is just checking SMTP mail flow. Not client connectivity.
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aandoAuthor Commented:
We finally fixed this issue by adding the mail server to a host file on the machine and manually configuring the Outlook instead of letting auto-populate do its thing.
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aandoAuthor Commented:
We found the answer.
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Craig BeckCommented:
Sounds like a workaround.  I'd check your autodiscover DNS entries.
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