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  1.    1 Week Ago #11
    Join Date : Oct 2014
    Posts : 17,588
    Windows 10 Insider Preview Build 16281
    Thread Starter

    As long as my VPN (Windscribe) is closed, Outlook collects email for those accounts. once it's turned on and the firewall is activated, everything goes to pot.

    Could the problem be Windows' firewall and the Windscribe firewall bumping into each other?
      My ComputerSystem Spec
  2.    1 Week Ago #12
    Join Date : Oct 2016
    Caledon, Ontario, Canada
    Posts : 4,063
    Windows 10 Pro Build 1703

    I would think it is more an issue that Outlook is not passing through Windscribe as planned, eg a rule or setting is missing.

    When you use VPN are you using anything to mask country of origin?

    Does Windscribe have any kind of logging tool on your device that you can access?
      My ComputerSystem Spec
  3.    1 Week Ago #13
    Join Date : Apr 2015
    Posts : 12,831
    W10Prox64

    You should find a Windscribe certificate in the Trust section of advanced settings in Outlook.
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  4.    1 Week Ago #14
    Join Date : Oct 2014
    Posts : 17,588
    Windows 10 Insider Preview Build 16281
    Thread Starter

    Quote Originally Posted by simrick View Post
    You should find a Windscribe certificate in the Trust section of advanced settings in Outlook.
    Not there.
      My ComputerSystem Spec
  5.    1 Week Ago #15
    Join Date : Oct 2014
    Posts : 17,588
    Windows 10 Insider Preview Build 16281
    Thread Starter

    Quote Originally Posted by Caledon Ken View Post
    I would think it is more an issue that Outlook is not passing through Windscribe as planned, eg a rule or setting is missing.

    When you use VPN are you using anything to mask country of origin?

    Does Windscribe have any kind of logging tool on your device that you can access?
    Yep, that's pretty much a given, Ken.

    I've opened a ticket with Windscribe, so we'll see where that leads me.

    No masks that I know of, and I'm not sure about a logging tool. Simrick uses WS, so maybe she'll know. I do know they erase everything three minutes after a session ends.
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  6.    1 Week Ago #16
    Join Date : Feb 2016
    Maribor, Slovenia
    Posts : 8,952
    Windows 10 (Pro and Insider Pro)

    Wynona, try to access Outlook with Windscribe's firewall set to off . It won't hurt your privacy. This is just in case your PC turns off and would reveal your real IP address to outside world, before windscibe kicks in...

    This would eliminate one unknown...

    @Wynona: while browsing MS forums I stumbled against one topic, similar to yours. While it won't show you any useful direction to solve your problem, it'll let you know, that you're not alone with it, and it may even give you a chance to smile (bitter sweet).
    We are also experiencing this problem. We have roaming profile domain accounts using Office 365 email with cloud Exchange servers. Each time the roaming account logs in it asks for Outlook credentials again to connect to cloud based Exchange. The credentials in Credential Manager don't seem to save with the roaming profile when the user logs out.

    An Internet search on the issue brought me to Andy's query in the Office365 forum. The Microsoft response in the Office365 forum was to post the question to the Outlook forum. The Microsoft response in the Outlook forum was to post the question in the TechNet Exchange Server forum. The Microsoft response in the TechNet Exchange Server forum was to post the question in the Office365 forum.

    Does anyone at Microsoft know how to answer Andy's question?
    Thank you.
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  7.    1 Week Ago #17
    Join Date : Apr 2015
    Posts : 12,831
    W10Prox64

    The problem is the Windscribe cert doesn't load into Outlook, probably because she's using Insider O365. It works if she shuts the "whole computer" VPN off, and only uses the browser extension. Tech support have to help her get the cert loaded properly into the Outlook email client. They also need to be made aware that this is a problem in Office Insider.

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    She does not have this cert showing in her client, and it needs to be there.
      My ComputerSystem Spec
  8.    1 Week Ago #18
    Join Date : Feb 2016
    Maribor, Slovenia
    Posts : 8,952
    Windows 10 (Pro and Insider Pro)

    Quote Originally Posted by simrick View Post
    The problem is the Windscribe cert doesn't load into Outlook, probably because she's using Insider O365. It works if she shuts the "whole computer" VPN off, and only uses the browser extension. Tech support have to help her get the cert loaded properly into the Outlook email client. They also need to be made aware that this is a problem in Office Insider.

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    She does not have this cert showing in her client, and it needs to be there.
    Simrick, and it's working with @ hotmail and @ live.... Don't think that's the main problem. Something on the outlook.com side have its share (or combination)

    There are about 10 to 15 possible different reasons for such behavior (regarding to quick analysis). Some of them are fixed in latest version (1710)

    Do you have the latest (stable) version Wynona?

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