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Why does my gmail keep asking for my password in Outlook?
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I have set up a gmail account in Outlook on my Laptop. I was getting my emails until yesterday. Today I keep getting a dialog box asking me to 'enter the user name & password for the following server 'pop.gmail.com. Even though I put in the correct password it refuses to complete the 'receiving' process, and tells me the password is incorrect. I can however access my emails on my Samsung tablet.
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You likely have added other accounts to your Gmail profile. Look at the section Check mail from other accounts via https://mail.google.com/mail/u/0/#settings/accounts
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Having the exact same issue and wanted to invite you to other relevant conversations.
Here are other active threads on this - no answers just yet - just want to pool our resources and ensure we're all talking to each other ...
 
Issue with Gmail in Outlook (sorry we couldn't sign you in to google - imap)
 
Connect Gmail to Mail and Outlook 365
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I have had this problem starting this past week. I have made no changes and my software is up to date. I believe this is related to Google making some change as many are experiencing it. I may have to get rid of using Google if I can't find a solution. Is this to try and stop others from using Outlook and only use online GMAIL? I hope not, since I like both and it would be a terrible thing to do morally.
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Not sure if I am having the same issue but if not it's close.  Every time I start Outlook lately Gmail asks for my password.  it's not an easy password to remember so each time i have to go to my password manager (of course that also needs a password) and copy the password, go back to outlook and paste the password into the dialog box. It doesn't sound like a big deal but every time i open Outlook this is happening and it's getting annoying.  I'm considering changing my password to something easy to remember.  I'm sure that's an unintended result of a policy change but I imagine i'm not the only one to be making that change.
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Volunteer in this Google supervised forum. Not a Google employee.
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Have you allowed for less secure apps?  Please do so, and see if that helps.  https://myaccount.google.com/lesssecureapps 
 
You may also need to clear a "captcha".  (You usually have only a 10 minute window after clearing the captcha, depending on what you are doing).
 
If using 2 Step Verification in Gmail, you may need an application  password. https://support.google.com/accounts/answer/185833?hl=en  
 
Use "recent" mode if you are using POP3 on multiple devices.  https://support.google.com/mail/answer/7104828?hl=en 
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I'm having the same issue as well. This only just happening to me recently. One of my Google accounts required to enter the password twice. Even I have enter the password correctly, they still ask me for more. I have agreed the new privacy policy but it seems they keep doing this. Outlook is great but it feels like they have just fix something that doesn't need to be fix.
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I have been having this problem also with Outlook 365. I have tried everything that has been suggested - changing profile, 2-step verification and app-generated password, less secure apps activation and the same keeps happening. I keep getting asked for my password once or twice accessing Gmail and also before accessing subfolders. Sometimes a dialog box appears telling me it's having trouble synchronizing but it eventually does. Like a previous user, if this continues I will have to abandon gmail. It's getting frustrating!
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The summary is that in Outlook your server settings (or account settings) need to be changed:
imap.gmail.com should be changed to imap.googlemail.com
and
smtp.gmail.com should be changed to smtp.googlemail.com

I'm not using two-factor authentication and this solution worked for me. Note that I disconnected from the network to make those changes so that the Google Mail pop-up window would not pop up again and again while I made the changes.
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Thanks Beth! That solution worked!

"See Andrew Gibbon's solution at https://support.google.com/mail/thread/6139701?hl=en
The summary is that in Outlook your server settings (or account settings) need to be changed:
imap.gmail.com should be changed to imap.googlemail.com
and
smtp.gmail.com should be changed to smtp.googlemail.com

I'm not using two-factor authentication and this solution worked for me. Note that I disconnected from the network to make those changes so that the Google Mail pop-up window would not pop up again and again while I made the changes."
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Just to update: my Windows 10 PC has just updated, presumably with a similar update to the one last week.  The repeated Google sign-in has not yet appeared.
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