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HOW TO: Solve a Repeating Password Error when Setting up IMAP with Gmail in Outlook

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Andrew Leniart
Helping others, to help themselves...
Read this tutorial to learn how to fix repeating password error prompts when setting up Gmail IMAP with Microsoft Outlook. The entire process is described with step by step, illustrated instructions. Enjoy...

On various tech forums that I frequent, as well as at Experts Exchange, I often see people frustrated with the process of creating an IMAP (Internet Messaging Access Protocol) connection because Outlook keeps asking for a password, despite the correct password having been entered. The repeating password error prompt when trying to configure IMAP with a Gmail account in Microsoft Outlook is a common cause of frustration.


So why does it happen? The password error frequently occurs if you have 2-Step-Verification enabled on your Gmail account. But do not turn off this great security feature just to get around the problem - there is a much better way. 


The same error can also occur if you haven't enabled IMAP correctly or have disallowed Less Secure Apps to connect to your Gmail account when not using 2 Step Verification to secure your Gmail account. 


In this tutorial, I show step by step instructions, including screenshots, of everything you need to do. I show the way to enable IMAP, and how I've set up Gmail IMAP in Microsoft Outlook for my clients' dozens of times, with steps that will work every single time. I also show how to allow Less Secure Apps to connect to your Gmail account, which is necessary for Outlook to be able to successfully connect via an IMAP or POP connection if 2 Step Verification is not enabled.


Follow this process and you can say goodbye to those frustrating Password Error prompts forever. This tutorial uses screenshots from Outlook 2016, however, the steps are similar with most Outlook versions.


The setup processes described in this article are ideal for when you utilize 2-step-authentication with Gmail and from my experience, they work every single time.


Tip! Click illustrative images below to get a full-size view in a new browser tab or window.


So let's get to it!


Enable Less Secure Apps in your Gmail Account


Note: This only applies to Google Accounts that do not have 2 Step Verification turned on. It is not needed if you are using 2 Step Verification to access your Gmail account.


Gmail periodically sends out a standard Email to all members advising them to check the security settings on their accounts. A few of my clients have heeded the advice, only to find that their Outlook, which would connect to their Gmail account without any issues, would suddenly start having password issues. Here's how to stop it.


  1. Go to the Less Secure Apps section of your Gmail account
  2. Now turn on Allow less secure apps
  3. Done. 


Enabling IMAP on your Gmail Account


The first thing to do is to make sure your Gmail account is IMAP enabled.


Log into your Gmail account, and click the Gear Icon, and then click "Settings"



On the Settings page, click the Forwarding and POP/IMAP setting.



Ensure your "IMAP Status Setting" is set to Enable IMAP as shown below.


The other settings can be left as default, however, I'll explain what they all mean below. Once you're happy with your settings, click the "Save" button to save them. You have now enabled your Gmail email account for IMAP.



What do the " IMAP Access: " options do?


  • Status: IMAP is disabled - This needs to be changed to a Green "IMAP is enabled" message if not already set, by simply clicking the "Enable IMAP" radio button and saving changes.

  • When I mark a message in IMAP as deleted: Auto-Expunge on or off determines how deleted messages will be treated. By leaving Auto-Expunge on, when you delete a message in Outlook, the same message will be immediately deleted from the Gmail server.

    I prefer to change this setting to "Auto-Expunge off" as shown above because then the IMAP connection is not constant even if Outlook is open. So if I accidentally delete a message in Outlook, I can restore it before the Gmail server is updated with my changes.

  • When a message is marked as deleted....etc: By turning Auto-Expunge to Off, we now have other options to consider. The default is to Archive the message. Pretty self-explanatory.

    I prefer to set that option to "Move the message to the Trash" so that the Gmail server will be the same as my Outlook.

    Setting the last option will delete the message forever, without an opportunity to recover it.

  • Folder Size Limits again is pretty self-explanatory. I suggest you leave that at its default - "Do not limit the number of messages in an IMAP folder."


Once you click "Save Changes" as per the image above, your browser will return you to your online Gmail Email account page. You can now close that page, we're done with it.


Once you've made sure that IMAP is enabled on your Gmail account, proceed to the next step.


Generating a Unique App Password in Google


The first thing you're going to need to do is to is create an "App Password" in your Google Gmail account to use with Outlook. Perform the following steps.


1. Log into your Gmail account and once logged in, click your name or the avatar of yourself 

2. Click the My Account button



3. Now click the "Signing in to Google" Link on the left of your browser screen



4. Under "Password & sign-in method", click "App Passwords" 



5. You'll now be prompted to enter your password again to verify that it's really you trying to access this security feature. That's expected, so enter your Google Gmail password and click the NEXT button



6. You'll now be on the "App passwords" page. Click the "Select app" drop arrow as shown below and select Mail. 


7. Then click the "Select Device" drop arrow and select the appropriate device. In this example, I'm setting up on a Windows Computer so that's what I've selected.


8. Once done, the "GENERATE" button turns from Ghosted to Blue and is able to be clicked. Click the GENERATE button.


If you've never set up an app password as yet, then you won't have entries similar to what you see below. If that's the case, all is fine, you'll have one soon.



9. Gmail generates an App Password called "Mail on my Windows Computer." Take a copy of the 16 character password in the yellow box - you'll need it later! 


10. Once you've taken a note or copy of the generated app password in the yellow box, click the "Done" button


*Note to any hackers reading this - Don't bother trying - the example below has already been revoked!  :)



That's all we need to do in Google Accounts, so you can log out or just close your browser now. It's time to get started with Outlook.


Setting up Outlook with Gmail using IMAP


The following set up example is showing Outlook 2016 - current at the time of writing. However, the basic principles and steps should be similar to all versions of Outlook.


A) Open Outlook and click File > Add Account



B) The Welcome to Outlook wizard pops up. Enter your Gmail email address in the box, click "Advanced Options" and put a tick in the box marked "Let me set up my account manually" and then click the "Connect" button.



C) A "We're getting things ready" box will appear for a few seconds and then you'll be prompted to "Choose an Account Type." Click on the IMAP icon.



D) Note the settings in the next screenshot and make sure yours are the same. They should be pre-filled in for you, but just in case they're not...



Here are the settings in written format if you want to copy and paste:


Server: imap.gmail.com  Port:  993

Encryption method set to SSL/TLS

Outgoing mail: smtp.gmail.com  Port: 465

Encryption method set to SSL/TLS


With that out of the way, click the "Next" button on the above window.


E) Here's where you need that 16 character App Password that we generated and copied in Step 10 above. Ignore the spaces in the generated password and just enter all 16 characters of the password on the following screen, and then click the blue "Connect" button.



If you get an error the first time, click "Try Again" - it always works for me on the second try. You should end up with the following "Account setup is complete" window.


F) I suggest you untick "Set up Outlook Mobile on my phone too" (you can set that up later) and then click the OK button.



Once the OK button has been clicked, Microsoft Outlook creates the IMAP account and begins populating it with all of the emails that are saved on the Gmail server. You will also find a Test Message automatically sent by Microsoft Outlook to test the connection.


The data file that Microsoft Outlook will create will be an OST (Offline Storage Table) and it will be located in:

C:\Users\YourProfileName\AppData\Local\Microsoft\Outlook\your-email-address@gmail.com.ost


This will not interfere with the operation of any PST files that you have.


Finished and Done!


Congratulations, you've now successfully set up an IMAP connection between Microsoft Outlook and your Gmail email service. No need to log into Gmail to deal with your Gmail email anymore - you can now do it all from the familiar GUI interface you've gotten used to in Outlook. 


To refresh Outlook and make sure it's synchronized with Gmail, simply click the Send/Recieve button. Or, if you prefer, ensure there is a tick in the following Outlook location;


File > Options > Advanced > Send/Receive > Schedule an automatic send/receive every xx minutes.


You can even have Outlook continue to check for any new mail and update itself when it's offline by putting a tick in the bottom Offline Settings value.



Conclusion


Every step described above was followed and tested during the writing of this article with Outlook 2016 on a Windows 7 Professional installation, so there should be no reason for it not to work in any supported version of Microsoft Windows. The process will also be very similar if using a Macintosh OS X, Windows 10 and others.


However, should you need further help on this process, I encourage you to use the free "Ask a Question" feature at Experts Exchange. I monitor questions asked about this topic and will be glad to help you further if necessary.


Author: Andrew Leniart


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Expert Comment

by:Scott Fell, EE MVE
Hi Andrew, I saw your answer here, https://www.experts-exchange.com/questions/29123600/Connect-MS-Outlook-2016-to-Gmail.html#a42717815 that mentioned this article. In your answer you talked about enabling less secure apps in your Google account but that is not covered here.  

When you generate an app password, does that mean you can skip the step for authorizing less secure apps to make outlook connect or do you still need to do that?
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LVL 23

Author Comment

by:Andrew Leniart
Hi Scott, thanks for reading my article. I've just scanned over it again and you're quite right, it was an oversight and got left out. I'll re-edit and correct that oversight shortly.

In answer to your question, I have had instances where Outlook would indeed claim an incorrect password when trying to connect if less secure apps were disabled in Gmail. Many thanks for pointing that out. Allowing less secure apps, however, is no longer necessary (or indeed even able to be accessed) when 2 Step Verification is turned on.

Regards, Andrew
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Expert Comment

by:The Kyrgyz Embassy
Hi there. Outlook started asking for user name and password few days ago. It has been working for several years now. I have done everything step by step. Changed password, removed account and installed again. Enabled POP and IMAP, Enabled less secure ap, Tried activating 2 step verification and app dedicated password. Result is the same it insists for user name and password with the pop up. Meanwhile all firewall and antivirus issues are rulled out. I can install other gmail account with no problem on my Outlook. What might be the reason. I am out of options, please help. I am running win 8.1 Pro with Outlook 2010. Kindest regards. Arvin
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LVL 23

Author Comment

by:Andrew Leniart
Hi Arvin,

Tried activating 2 step verification and app dedicated password. Result is the same it insists for user name and password with the pop up.

Strange. That should have cleared any username/password error. I've set up many Outlook / Gmail IMAP and POP accounts for my clients and the process described in my article has worked every time without fail.

I can install other gmail account with no problem on my Outlook

In that case, it's possible your Gmail account may have been compromised. Please go to the following link in a web browser:

https://mail.google.com/mail/u/0/

Try to log in with the problematic account. Are you able to? If not, then you will likely need to reset your password on that account. I did note you mention earlier that you tried changing your password so the difficulties you're having don't make sense to me.

My only other suggestion would be to remove the account from Outlook and go through the steps I've listed 1 by 1 without missing any of the steps at all. Recheck that everything is as per my article. It has to work - it's worked for me to fix password related errors dozens of times now.

Finally, if still unable to connect, temporarily disable both Firewall and Antivirus apps when you try to connect the first time.

Also, please confirm if these are "Free" or paid "G-Suite" Gmail accounts. The process may be a little different on G-Suite accounts.

Let me know how you go.

Regards, Andrew
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Expert Comment

by:The Kyrgyz Embassy
Dear Andrew,
Thank you for taking your time and addressing my issue.

All the steps you advised were followed letter by letter.

Changed password when problem started.

Tried to login to gmail clicking URL you provided - It is OK. I can log in.

The fact that I can install other gmail account with no problem sortes out firewal and anti virus issue. Yet tried with Anti Virus and firewall turned off - did not help either.

It is free account.

Is there any possibility that gmail could block my POP account? Some forums say that if the Send/Receive periods are short Gmail sees it as spam account and may block your account. I have increased this period to 15 mins. Is there known or safe time allocated? If this is the case - how I check this and unblock.

All steps as per your noted are followed. Problem persists. Pop up comes and asks for user name and password.

Error it gives as follows: (Needles to repeat my user name and pass are OK, I can login via browser.)

Receiving' reported error (0x800CCC92) : 'Your e-mail server rejected your login. Verify your user name and password in your account properties. Under Tools, click E-mail accounts. The server responded: -ERR [AUTH] Authentication failed.'.

Perhaps I should note that I am it professional with 17 years experience. On a daily bassis we are installing many accounts.
This problem seems to be related to this specific account. Any advise to solve would be verry appreciated.

Kindest regards,
Arvin.
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Author Comment

by:Andrew Leniart
Hi Arvin,

Perhaps I should note that I am it professional with 17 years experience.

Yes, that is useful to know. It changes the amount of detail I need to include in my replies to you, so thanks for advising me of that.

Is there any possibility that gmail could block my POP account?

Yes, that's always possible, but I can't think of a reason GMAIL would do that unless the account was used for sending spam or you were infected with Malware at some stage. It's also possible that Gmail account has been compromised at some point in the recent past and used to Spam with. I note that you've already changed your password on the problematic account, so that's a wise precaution.

As you've probably already discovered, Gmail Support for free accounts is next to useless - there is no direct email support for free Gmail accounts, only for paid G-Suite accounts.

That said, you can get in touch with them by using the following method:

  • Login into the problematic Gmail account with a browser
  • Click the Setting Icon Cog at top right
  • Select the "Send Feedback" option
  • A Send Feedback box will open asking you to "Describe your issue, or share your ideas"

Explain your issue in the above box and hit Send. That's the only method I know of to contact Gmail Support directly. Don't hold your breath for a speedy response though. I've managed to get some help a couple of times when troubleshooting for clients, but expect any help to include suggestions to switch to a paid G-Suite service if your experience is anything like mine have been.

Is there known or safe time allocated?

Not that I know of. The 15 minutes you've set it to sounds more than reasonable to me.

how I check this and unblock.

Assuming that is the issue and that your account has been blocked, then only Gmail support will be able to answer that one for you. I know of no self-help method to remove a Gmail server block of an account, but I would expect that you would have received an email advising that a block had been placed, so if you didn't, then I doubt that will be the cause.

Receiving' reported error (0x800CCC92)

That's just a standard Username/Password error, which doesn't help much to resolve your issue by knowing that given everything you've tried.

This problem seems to be related to this specific account. Any advise to solve would be verry appreciated.

I can't offer any help from the Gmail side - only support can do that so try contacting them in the method I've described above to verify that there isn't a lock on that particular account.

To rule out a problem in Outlook itself, I would suggest the following;

Create a new Windows user profile on the machine and try setting up the problematic account in outlook on that profile. That will rule out any Windows and Outlook Profile Issues if you strike the same problem in a fresh Windows profile. If you're successful, however, then you will know that there is an issue with either the Outlook or the Windows profile that you are having difficulties with.

The only other suggestion I can think of is to create a new free Gmail account and start again, populating it with the current mail and settings from the problematic account that you can access via a browser.

Apart from those suggestions, I've drawn a blank. Suggest using the Ask a Question feature at Experts Exchange and describe your problem in a question. Some other experts here may have struck the issue and be able to offer some ideas.

Good luck and please do let me know how you went with the above suggestions.

Regards, Andrew
0

Expert Comment

by:The Kyrgyz Embassy
Thank you so much Andrew for your time,
I will defenetely share results as soon as I sort this out.
Meanwhile I would like to share some details. I have tried to set up outlook using this account on fresh installed PC and sorted out the "User Profile" and Certificate issues. After trying all options I am confident that this is not general issue and precisely this account related issue. Cose' when I try to install other gmail account on that PC it goes smooth. Checked incoming mails and outgoing mails. Account never sended more than 100 mails per month - so account is not spammer. (In fact this is embassy's non essential communication address). Likewise never received mail noting it was blocked. I will use "Send feedback" option right away and will share results if I receive. Many and sincere thanks for your time and attention. Have a nice life. Arvin.
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LVL 23

Author Comment

by:Andrew Leniart
Pleasure Arvin and I look forward to your update. Also, if you found my article helpful in any way, if you could click the Thumbs Up button at the bottom left at the end f the article to endorse it, I'd much appreciate it :)  Regards, Andrew
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