Correctly configured Gmail continually prompts for password in Outlook

[carmen617]

Anybody else see this issue? I seem to run into it a few times a month and I haven't found a solution yet. Outlook is correctly configured with an IMAP Gmail account. Send and receive is very slow, and Outlook constantly pops up a password prompt. Cancelling the prompt a few times makes it go away, and eventually the send/receive completes and the password prompts stop coming - until the next time.

Suggestions? Thanks!

 

[MichaelBits]

What version of outlook?

Perhaps this? Allow less secure apps.
https://support.google.com/accounts/answer/6010255?hl=en

 

[nerd2u]

Why not just use Gmail? Why have it in Outlook?

Sent from my SM-G870W using Tapatalk

 

[HCHTech]

Try opening Outlook by right-clicking on the icon and choosing 'Run as Administrator'. Let it prompt and enter the correct password. Then close Outlook and use normally after that.

 

[HCHTech]

Why not just use Gmail? Why have it in Outlook?

Maybe they have more than one email address and want to have access to everything in one program...or maybe they've been using Outlook for 20 years and don't want to learn something new.

 

[Diggs]

Secondary authentication in Google's settings need to be adjusted?

 

[carmen617]

I've seen it in more than one version of Outlook, but the current client was using Office 365 on a brand new Surface - which, btw, shipped with Windows 10S, and I had to "upgrade" to Windows 10 Pro before I could do anything else with it. That's quite a strange decision for Microsoft to make with a $1700 laptop.

And yes, many people have multiple email accounts, or other reasons to want to use Outlook. In this case the client has two IMAP accounts, and also wants to sync her Apple contacts and calendar with her Surface - this is a job for Outlook.

The problem isn't about allowing less secure apps, or using an app specific password - Outlook is configured correctly, mail sends and receives, it's just slow and continually asking for a password when the correct password is clearly already stored in the system (otherwise there would be no send and receive, obviously.) The internet connection is fine, and the other accounts have no issues.

 

[HCHTech]

Maybe this is Google's way of 'disincentivizing' the use of Outlook. I wouldn't put it past them. For an example, open Edge, let it finish loading the incredibly slow MSN page and Bing search, then type www.google.com into the address bar and time how long it takes to go there. There is no way that MS isn't slowing this down one way or the other.

 

[fincoder]

The problem isn't about allowing less secure apps

Does this mean you've logged into the Google account and checked that allowing less secure apps is enabled? It needs to be for Outlook.

continually asking for a password

Outlook will do this for any login failure (not just user/password issue). The detail of the error message (in the send/receive dialog box) should contain text returned by the server to indicate the reason.

Why not just use Gmail? Why have it in Outlook?

Why use the Gmail website? Why not have it in Outlook?
Surely every moderate or heavy email user would prefer to use a dedicated email client instead of clunky webmail, and Outlook is one of the best email clients.

 

[Markverhyden]

Out of curiosity how was the account setup? Was setting up a new laptop couple of days ago and needed to add the GMail account, which was using their domain. No matter what I did I kept on getting authentication failures. After doing some digging around I came across GSSMO, a tool which specifically sets up Outlook to work with GMail. Maybe give that a shot to see what happens.

 

[Diggs]

Does this mean you've logged into the Google account and checked that allowing less secure apps is enabled? It needs to be for Outlook.

This! Always a show stopper with Outlook. Thunderbird will walk you right through and allow Google to verify, but not Outlook.

 

[carmen617]

Out of curiosity how was the account setup? Was setting up a new laptop couple of days ago and needed to add the GMail account, which was using their domain. No matter what I did I kept on getting authentication failures. After doing some digging around I came across GSSMO, a tool which specifically sets up Outlook to work with GMail. Maybe give that a shot to see what happens.

This particular account has 2FA on it, so I had to use an application specific password. However, my stepmother, who has the exact same problem, doesn't have 2FA on her gmail, so I have to set Google to allow less secure apps. It's one or the other with Google, although for this client less secure is also on.

I actually think the problem is due to poor internet connection, which, for some reason, Gmail with Outlook is more sensitive to. I minimized the problem, but didn't solve it, by setting a longer server timeout for my stepmother. That didn't seem to have an affect with this client, but she was a new setup and had a lot of folders and sub-folders to populate.

GSSMO is for G-suite, the paid version of gmail. I don't think it works for free gmail accounts.

 

[fincoder]

his particular account has 2FA on it, so I had to use an application specific password... It's one or the other with Google, although for this client less secure is also on.

Thanks for clarifying. When you said 'it's not an issue with allowing less secure apps' it sounded like you were assuming. As you know, when troubleshooting it's necessary to eliminate assumptions!

I actually think the problem is due to poor internet connection, which, for some reason, Gmail with Outlook is more sensitive to.

You're probably right, but you could turn off 2FA as an experiment and see if it helps. Does allowing less secure clients negate the security benefit of having 2FA turned on?

 

[carmen617]

Thanks for clarifying. When you said 'it's not an issue with allowing less secure apps' it sounded like you were assuming. As you know, when troubleshooting it's necessary to eliminate assumptions!

You're probably right, but you could turn off 2FA as an experiment and see if it helps. Does allowing less secure clients negate the security benefit of having 2FA turned on?

Good question, except as I said I've seen the same issue with a non-2FA account with less secure apps turned on. I'm not at the client's right now, so I can't troubleshoot on that level. I actually connected my own gmail account, which I rarely use but has 2FA on, with my own Outlook to see if I have any issues. Since I've seem this problem with multiple users (and now that I think of it, the last 3 have subscription Outlook) I was hoping it would occur for me as well - so far it's a little slower to sync than my other email accounts, but not asking me to reenter my credentials.

As I said, I think it's some sensitivity to less than robust internet connections. I was hoping through this post to find someone who had tweaked Outlook or Gmail to minimize the annoyance.

 

[nerd2u]

Is there not an option in outlook to turn on slow internet connection connectivity?

Sent from my SM-G870W using Tapatalk