Really Odd Gmail/Outlook Client Behavior

Apologies in advance for the complex issue description. I am at my wits end and, as anyone who has ever tried knows, getting any meaningful Google help/support is pretty much impossible.

-1) This is a very recent (as in just this week) issue; I have been using an installed version of Outlook client to access Gmail on my desktops forever, with several Gmail addresses hooked up to it.

-2) The only account that is experiencing an issue is my main use/primary account. Technically speaking, though, there is no difference between how these accounts are set-up (AFAIK), either in Outlook or out on Gmail, or in how they are used…

2.1) …with the only exception that my primary email (the one I am having an issue with) is also set-up on my mobile phone (with a non-Gmail client). It does not have any issues sending/retrieving email for this account. I don’t think this is diagnostically relevant, but it is the only difference I can think of.

-3) I have always set up these accounts with POP3; I’m not interested in IMAP. I DO have “less secure apps” toggled on for this, and all, of my Gmail accounts.

-4) What I experience is some sort of security/authentication issues…it’s probably not diagnostically relevant, but Outlook responds with:


But the credentials entered are correct and reentering them manually does not help.

-5) I can “solve” the issue in the very short term (like for a matter of minutes or one auto send/receive cycle?) by using this link: It “works” on any browser, as in Chrome, Edge, or Firefox, and I can always sign into my Google account via browser with no issue, i.e. this has to do with Outlook specifically (it would seem). Note: it almost never presents a “captcha” thing…?

5.1) The DisplayUnlockCaptcha URL even “works” if I use it on DMS Jump server; I can then immediately perform a successful “Send/Receive” operation within Outlook on my desktop. But in both cases, the security/authentication failure, via the Outlook dialog above, reoccurs very shortly thereafter.

-6) I do have a VPN (Windscribe) installed on both my desktop and within my main (Firefox) browser. But, again, I have had it installed for a while now, and I have other email accounts that work just fine.

Any thoughts or suggestions?

Launch Outlook
/ File / Office Account / Account Privacy / Manage Settings / All connected experiences / tick “Enable connected experiences” / OK / restart Outlook**

If it’s already checked, uncheck it and try that.

1 Like

Thanks for the suggestion :–)

We have very different versions of Outlook, though…my File dropdown menu looks like this:


Based on that logo, you are using Outlook 2007 - 2010

There’s a few things here - no support for this anymore (obviously)
You can try to add the domain to “Trusted Sites” in IE and see if that helps

1 Like

I went ahead and tried this, although it was a kind of a hail mary, since issue really seems to be Google related w.r.t. this specific account (as evidenced by ability to actually send/receive once the DisplayUnlockCaptcha URL has been clicked).

Sadly, the “Trusted Sites” suggestion did not seem to have any effect. :sob: Thanks again, though.

Marshall, I solved this with my Outlook 2016 by using two factor authentication and gettting Google to give me a second key to login. Something like this: How to set up two-factor authentication (2FA) for Gmail in Outlook | Windows Central

1 Like

Thanks Dan. I did a lot of Interneting before posting and had seen this listed on Google support site as a potential option/solution. But my >curiosity+bee-in-bonnet< wanted to understand why the issue only occurs for one out of the 4 Gmail addresses I have set-up, and use, in almost exactly the same way? I am pretty sure there will/can not be any answer forthcoming on this because I am willing to bet even the dolts at Google/Gmail support wouldn’t be able to explain it even if their lifetime memberships in Antifa depended on it.

But it is clear to me at this point, after screwing around a bit more, that this is entirely related to Google’s reaction to my VPN: when I turn it off, everything is fine…when I turn it back on, the problem for this particular email account re-surfaces. I’ve switched

So at the point I have to screw around with 2FA or bespoke app passwords, especially for arbitrary Google considerations rather than my personal choice to do so, I’d rather just cut the apron strings, dump Microsoft and Google, and switch over to Thunderbird and one of the several privacy-oriented email services out their (like Proton, Hushmail, Zoho, several others) that don’t punish users simply for being concerned with their privacy.

I hadn’t checked into Thunderbird in a while…I am very happy to see that one of the reasons I was hesitant to switch over in the past, as in the lack of well-integrated calendar and task management feature sets, has been addressed over the last few years. Good on them!

1 Like

This is absolutely a VPN issue. I had the exact same problem.

Google is trying to be too helpful and getting it just plain wrong!!!

I ditched GMail for exactly this issue.

Thankfully I have my own domain so I never need to actually change my email address, only my provider.