Outlook is a popular email client developed by Microsoft. It has become one of the major platforms used for business communication because of its convenience, ease of use, and security. However, it’s not uncommon to come across glitches and bugs when using Outlook.

Some users have reported that Outlook keeps asking for their passwords when connecting to Microsoft Office 365. When you cancel the prompt, it throws up an error message that reads, “The connection to Microsoft Exchange is unavailable. Outlook must be online or connected to complete this action.”

This happens even after you have successfully logged in. The continuous Outlook password prompt seems to mostly affect older versions of Outlook. The good news is that the issue is fixable, and in this post, we’ll show you how to stop Outlook from asking for your password when connecting to Office 365.

Why Does Outlook 365 Keep Asking for a User’s Password?

Here are some of the possible reasons that could lead Outlook to keep asking for your password:

  • There is likely to be a problem with your Outlook app’s settings.
  • If you have recently updated or upgraded your OS, your new settings might be triggering the issue.
  • Your profile could be configured in such a way that it needs to authenticate your credentials every time you send an email.
  • Your profile could be corrupted due to a malware attack.

How to Stop Outlook From Continually Prompting for a User’s Password

To resolve this problem, here are a few workarounds that you can try.

Solution 1: Clear Your Cached Passwords

Start by clearing your cached passwords using the Control Panel. To do that, follow the steps below:

  1. Press the Windows logo key on your keyboard and look for “Control Panel”.
  2. Once you open it, search for “User Accounts”, and open the link.
  3. In the right pane, look for the link that says “Credentials Manager” and select it.
  4. Search for saved logins that have the word Outlook in their names and select each one of them to display more options. Click on “Remove” to delete them from your PC.
  5. Close Control Panel and restart your PC.

This fix should get rid of the error. If it doesn’t, check out the next fix.

Solution 2: Set the ‘Logon Network Security’ Setting to Anonymous Authentication

If you’re using an older version of Outlook, the ‘Logon network security’ setting in the Microsoft Exchange dialog box may be set to a value other than Anonymous Authentication. To fix this issue, follow the simple guide below:

  1. If Outlook is running, close it.
  2. Go to the Control Panel (as shown in step 1 above), and set the “View by:” setting to “Large Icons”.
  3. Locate “Mail” and click on it to open it.
  4. On the next screen, click on the “Show Profiles…” option.
  5. Choose your profile and then click on “Properties”.
  6. Click on “E-mail Accounts”.
  7. In the “Account Settings” window, select your email account and click on the “Change” option.
  8. On the next screen, select “More Settings”.
  9. In the “Microsoft Exchange” dialog box, click on the “Security” tab and choose “Anonymous Authentication” from the “Logon network security” list.
  10. Click “OK”.
  11. Click Next > Finish.
  12. Exit the “Account Settings” and “Mail Setup” dialog boxes.
  13. Exit the “Mail” control panel.

This workaround should stop Outlook from repeatedly asking for your password when connecting to Office 365.

Solution 3: Enable the Remember Password Option

Many sites nowadays offer the option to remember passwords so that you don’t have to enter your credentials every time you log in to your accounts. Outlook also offers you that feature, and you may be getting the error because the ‘Remember password’ option is disabled.

Try re-enabling this option to check if it fixes your problem. Here’s how:

  1. Go to the Cortana search bar (or press Win + S), type in Outlook, and then press “Enter”.
  2. Click on the “File” tab, and select “Account Settings” to open a list of options.
  3. Select “Account Settings”, find your account under the “E-mail” tab, and double-click on it.
  4. On the screen that appears next, under the “Logon Information” section, check if the “Remember password” checkbox is checked. If it isn’t, check it.
  5. Click “Next” to save the changes.

Solution 4: Disable the ‘Always Prompt for Logon Credentials’ Option

If you’ve set Outlook to always prompt for logon credentials, it may explain why the application keeps asking you for a password when connecting to Microsoft Office. To resolve this issue once and for all, follow the steps below:

  1. Launch the Outlook app and click on the “File” tab.
  2. Click on “Account Settings”, and choose “Account Settings”.
  3. Click on your email account to highlight it, and then click on “Change”.
  4. Click on “More Settings…” and move to the “Security” tab.
  5. Uncheck the option that says “Always prompt for logon credentials” under “User identification”.
  6. Click “OK” to save your changes and close Outlook.

Solution 5: Use a New Outlook Profile

If, for some reason, your Outlook profile has been corrupted, you may run into issues, like the Outlook password error. Creating a new profile might help fix the problem. Here is how to do so:

  1. Close Outlook.
  2. Open the Control Panel. Simply press on the Windows logo key on your keyboard, type in “control panel” (without quotes), and hit “Enter”.
  3. Select “User Account” and open the “Mail” link in the right pane.
  4. On the pop-up screen, open the “Show Profiles…” option.
  5. Under the “General” tab, click on “Add” and name the new profile.
  6. Click “OK” and fill in your details.
  7. Click “Next”, and then click “Finish”.
  8. Now enable the “Always use this profile” option.
  9. Click “OK”.

Solution 6: Update Outlook

If the above solutions don’t yield positive results, there could be something wrong with your Outlook app. In that case, updating it could fix any bugs. To update Outlook, follow these steps:

  1. Run the Outlook app, open File > Office Account.
  2. On the right pane, you’ll find the “Update Options” setting. Click on it, and select “Update now”.
  3. Once the updates have been installed, relaunch Outlook to check if you still experience the password issue.

Bonus Tip: Scan Your PC for Malware

Your computer may be infected by a virus or another type of malware that’s causing the Outlook app to malfunction. It’s time to take action. Criminals are known to infect computer systems with all sorts of malware to harvest confidential details, like passwords and banking information. They then use this data to steal from you or blackmail you.

To avoid such risks and do your business online with peace of mind, we recommend installing a robust security solution such as Auslogics Anti-Malware. This program comes with advanced features that enable it to detect any kind of malware, including threats camouflaged as useful files or programs. These are the types of malware that your ordinary antivirus software may fail to detect.

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We hope these solutions help you to stop Outlook from repeatedly asking for a password when connecting to Office 365. For queries, suggestions, or additional information, feel free to comment below.