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Outlook in Office 365 almost unusable with VPN

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Monday, October 15, 2018 7:35 AM | 1 vote

I've been testing Outlook in Office 365 (Outlook 2016 it seems) and so far I cannot get it to behave even well enough to be usable when on a VPN. I'm living at a hotel and must use the VPN. The service gives me excellent speeds and stability and I'm on Ethernet. All works like a top (I can even do video production here and upload videos really fast.)

Outlook takes forever to load and open the profile even if there's next to no new messages to sync and, worse, it takes forever to send an email -- it says "Preparing to send/receive" and "Trying to connect" when it had already been connected.

I'm running a business and know better than to operate on a hotel's Internet with using the VPN. The VPN service I use is NordVPN, which I assume is about as good as it gets based on a lot of posts on forums by techs having the same issue -- and that's my concern: I'm finding a ton of techs posting issues with Office 365 and especially Outlook when using a VPN, especially with Windows 7 though some also with Windows 10.

I'm still running Windows 7 on all my machines. It will not be viable to upgrade to go to Windows 10 for at least a few months.

NordVPN tech support is useless. They tell me to input an address into the Default Gateway and that doesn't seem to do a thing. Other than that, I'm apparently out of luck. (I already tried going to TCP, I don't use CyberSec, and "restart the network location awareness service" doesn't help either. The only thing left I can even think to try is to adjust the MTU setting, which is a bit above my knowledge level and which I don't have a lot of hope in at this point, but I can dig into it if it might solve this.) 

Any suggestions? Or is this really hopeless?

Should I bite the bullet and go for the stand-alone version of Office 2016 and put it on my three machines and call it a day?

Thanks!

Jay

All replies (4)

Monday, October 29, 2018 9:22 AM âś…Answered

SOLVED!

I found in another, rather extensive, thread that Hotspot Shield works fine with Office 365, and thank goodness that has been my consistent experience after a week of testing on multiple Windows 7 machines.

It's not the VPN for people who want absolute anonymity from their VPN, but for normal business use this seems to not only solve the Outlook/Office 365 issue but it works infinitely more crisply for me than NordVPN did.

Jay


Tuesday, October 16, 2018 10:08 AM

Hi Jay,

What's your email account type configured in Outlook 2016, Exchange account, Hotmail.com Microsoft account, IMAP or POP? Currently, it is hard to determine if the issue is related to Outlook connection or VPN connection.

Please click Send/Receive, send/receive all folders and check the process, confirm if there is any error when you send and receive emails.

I suggest you can create a new Outlook profile under VPN connection, setup this account in new profile, confirm if you can configure the account properly and send/receive emails.

Best Regards,
Winnie Liang
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Tuesday, October 16, 2018 6:52 PM

I should probably clarify and update a few things:

1. I am using perhaps the largest and most advanced Exchange hosting service, who I've used for fifteen years. In the past I have always used stand-alone installations of Office/Outlook with no problems whatsoever ever.

2. I have tested this on three machines now and the problem is consistent -- all running Windows 7.

3. There is not a question of connecting or of Sending/Receiving etc. The issue is that there is a massive "lag" of up to five minutes in "most" instances to do simple things like open Outlook and load the profile or create a New email or Reply to an existing email. It always "eventually" completes all actions, and occasionally it does so within seconds as it's supposed to (there is no rhyme or reason as to why is occasionally works properly). All testing confirms the issue is only when the VPN is connected. And 100% of everything else on this machine runs like a top even with the VPN connected (including Word and Excel in Office 365, and including very demanding apps like Adobe Premiere Pro and doing uploads of large video files, etc, etc). And before I uninstalled Outlook 2010 stand-alone, that worked like a top on this machine with the VPN running, as well. The issue is ONLY with Outlook in Office 365 (I have not tried using OneNote or OneDrive but other reports suggest those are often problematic with a VPN as well, in addition to Outlook)!

4. There are a great many posts in a lot of threads online, including in TechNet, about others having issues using Outlook, OneNote and OneDrive with a VPN. I have seen well over a hundred posts from tech managers about this to date. There is no consistently reliable solution. Here are just a few of the many threads I found about this:

https://answers.microsoft.com/en-us/msoffice/forum/msoffice_outlook-mso_winother-mso_2016/outlook-20132016-office-365-not-connecting-when-on/12889fee-5e63-4196-b746-8aa78939a9b0

https://techcommunity.microsoft.com/t5/Identity-Authentication/Can-t-Authenticate-to-Office-365-Over-VPN-through-office-apps/td-p/139935

https://blogs.technet.microsoft.com/the_microsoft_excel_support_team_blog/2014/03/24/office-2013-reports-no-internet-connectivity-with-vpn-connection/

5. NordVPN tech support has escalated the case for me and they told me the same thing, that it is a widely known issue that has persisted for years and Microsoft has yet to fix it, and NordVPN has been trying to create a workaround but thus far they have not succeeded. Here's a quote from the last email they sent me on this:

"This is an issue that most VPN services suffer from. For now, we do not have a workaround for this, but our developers are aware and are trying to come up with a solution."

So, troubleshooting my machine or configuration is not the way this is going to be resolved. It's a question of whether Microsoft can address it on a broader scale or not -- and if some "senior-level" tech can help by looking into this, doing some real research, and making some suggestions for me beyond what's in all those threads.

Otherwise, well, consider this a "bug report" or something and pass it on, though I assume the development team at Microsoft must be well aware of this by now given the massive volume of posts about it on the forums.

Jay


Saturday, October 20, 2018 7:08 PM

I will take a wild poke at this, but something to check.  ...Printers....  The Office suite products all initialize printers when you start up Outlook & Word specifically.  What we have noticed is that depending on the printer and the print server location, the communication cycle that going on can be painful.  We have people moving from office to office on a WAN and they bring all the printers for a remote office, over time they have like 20 printers.  And Outlook wants the status on all of them before it finishes starting up.  As well since Word runs inside of Outlook as the editor, it seems to have it's out version of this too.

So get rid of printers connections you don't use any more.  You could also set your default printer to the build in PDF printer.  You can have offline printers (such as connections to your home printer), as long as they can not resolve, Word/Outlook will give up quickly.

The worst are Plotter or highly customize print drivers instead of the build-in Windows mode drivers.

Sidebar: One more item to know about Windows 10 and networks.  Within Windows Explorer is 'Quick Access' for recent files.  This can be useful, but again, when Windows Explorer or 'Open dialog boxes' are access, Windows 10 will then access and open all those recent files to get attributes and preview images from them.  It does not seem to cache this info.  (You can change the default from Quick Access to This PC, if it causes issues).

Hope some of that triggers new ideas.

DJ