How Do I Fix Outlook Keeps Asking for Password Again and Again?
Are you frustrated because Outlook keeps asking for password again and again, even after you’ve entered it correctly? You’re not alone and the good news is, there’s a quick fix. Whether you’re using Outlook on a Mac or Windows, this blog post will walk you through an effective solution for this annoying issue. Stay with us as we break down the steps to finally put an end to the constant password prompts.
This problem often occurs when MS Outlook fails to properly authenticate your account, even after entering your credentials. On Mac systems, one common culprit is a glitch or corruption in the Keychain Access app, which stores login information for email accounts. When Keychain malfunctions, Outlook can’t retrieve the saved password properly, causing it to repeatedly prompt for your credentials. In this guide, we’ll show you a simple but powerful method to repair the Keychain issue and restore Outlook to normal functioning with no more endless password requests.
Outlook Keeps Asking for Password Again and Again on Mac – Real User Experience
“Hi everyone! I work at a well-known company where we use Mac systems across our teams. Recently, some of our machines were hit by a virus. We managed to fix the issue by formatting the affected Macs. However, after setting everything back up, we started facing a new problem. On Outlook 2016 for Mac, users are being asked to enter their password again and again while connecting to Exchange even though the credentials are correct. I’ve already double-checked the account and profile settings, and everything seems in order. I’m wondering if this could be a post-formatting bug or something deeper. If anyone has faced this or knows the real cause and solution, I’d really appreciate your help!”
This kind of recurring password prompt is more common than you might think, especially after system resets or updates. In the next section, we’ll explore what’s likely causing the issue and how to fix it quickly.
Why Does Mac Outlook Keep Asking for Password? Here’s What’s Really Happening
Mac systems are known for their top-tier security and dependable performance. One of the key features that supports this reputation is Keychain Access, a built-in password manager designed to securely store login details for apps and services, including Microsoft Outlook.
However, things can go wrong. When Keychain Access becomes corrupted or misconfigured whether due to system updates, formatting, or unexpected glitches, it can disrupt how saved passwords are managed. One common result is the creation of multiple conflicting tokens related to your Outlook account. This duplication causes confusion during the authentication process.
As a result, even if you enter the correct password, Outlook gets “stuck,” repeatedly asking for your credentials. It’s not that Outlook doesn’t recognize your password, it’s that Keychain Access is no longer managing it correctly. This issue is especially common in Outlook 2016 and 2011 for Mac, where the app relies heavily on Keychain to verify user identity.
So if Outlook keeps prompting you for a password on your Mac, chances are the problem lies within your Keychain and fixing it is the key to stopping those endless pop-ups.
How to Fix Outlook Keeps Asking for Password on Mac Operating System?
If Outlook 2016 on your Mac keeps prompting for a password when connecting to Office 365, a corrupted Keychain Access is often to blame. This can interfere with the way Outlook saves and retrieves your login credentials.
Follow the steps below to clear the problematic data and stop the password prompts:
1. Quit Outlook
- If Outlook is currently open, close it completely before proceeding.
2. Open Keychain Access
- Go to Finder in macOS.
- Click the Go menu at the top of the screen and select Utilities.
- In the Utilities folder, double-click Keychain Access.
Alternatively, press Command + Space to open Spotlight Search, type Keychain Access, and hit Enter.
3. Search and Remove Old Exchange Entries
- In the Keychain Access search bar (top-right corner), type: Exchange
- Look through the results and delete all items related to your Exchange account:
- Right-click each entry and select Delete.
- Repeat this step until all Exchange-related entries are removed.
4. Search and Remove ADAL Entries
- Now, type adal into the search bar.
- Select all items labeled as MicrosoftOffice15_2_Data:ADAL:
- Hit Delete key or right-click and choose Delete.
5. Delete Microsoft Office Identity Files
- Type office into the search bar.
- Locate the following items: Microsoft Office Identities Cache 2 and Microsoft Office Identities Settings 2
- Delete both of these files as well.
6. Close Keychain Access
- Once you’ve removed all the necessary entries, close Keychain Access.
Easy Manual Methods to Resolve “Outlook Keeps Asking for Password” in Windows
#1: Clear Saved (Cached) Passwords Using Credential Manager
Sometimes Outlook keeps asking for your password because it’s trying to use outdated or wrong saved credentials. Here’s how to clear them:
- Open Microsoft Outlook and the Control Panel at the same time.
- In Control Panel, go to User Accounts > Credential Manager > Windows Credentials.
- Look for any entries related to Outlook, MicrosoftOffice, or MS Exchange.
- Click on each one and select Remove to delete the saved passwords.
Once done, restart Outlook and enter your credentials again when prompted. This time, they should be saved correctly.
# 2: Disable “Always Prompt for Login” Option in Outlook
If Outlook is set to always ask for login details, you’ll keep seeing the password prompt even if your credentials are correct. Here’s how to turn that setting off:
- Open Outlook and go to the File tab.
- Click on Account Settings > then choose your Exchange account.
- Select the Change option.
- In the new window, click on More Settings.
- Go to the Security tab.
- Uncheck the box that says “Always prompt for logon credentials.”
- Click OK, then Next, and finally Finish.
Restart Outlook to apply the changes. This should stop the repeated password prompts.
#3: Create a New Outlook Profile to Fix Corrupt Data
Sometimes, Outlook can’t remember your password because the profile itself is damaged. Making a new profile can fix the problem.
Steps to create a new Outlook profile:
- Open the Control Panel and click on the Mail option.
- Click on Show Profiles.
- Select Add, enter a name for the new profile, and click OK.
- Enter your email account details and click Finish.
- Under “Always use this profile,” opt the fresh profile from the dropdown.
- Click Apply and OK.
Now, open Outlook with the new profile. The password prompt should no longer appear.
#4: Reset or Modify Outlook Login Credentials in Credential Manager
You can also reset or remove outdated login credentials using Credential Manager in Windows.
Steps to reset credentials:
- Open Control Panel and go to Credential Manager.
- Select Windows Credentials.
- Look for any entries related to Microsoft Outlook or your email address.
- Click the arrow to expand each entry and then select Remove.
- If a warning message appears, tap Yes to confirm.
Repeat this process for all Outlook-related entries. Restart Outlook and enter your credentials again.
#5: Use NTLM Authentication for Outlook Anywhere
The Outlook Anywhere feature lets users to access their company email remotely. Setting the authentication method to NTLM can help solve password prompt issues.
Steps to configure NTLM authentication:
- Open Outlook, go to the File tab > Account Settings > Account Settings.
- Select your Exchange account and click Change.
- Click on More Settings, then go to the Connection tab.
- Click Exchange Proxy Settings.
- Under Proxy Authentication Settings, choose NTLM Authentication from the dropdown.
- Click OK, then Next, and finish the setup.
Final Thoughts
If you’ve tried all the manual methods and Outlook still keeps asking for password, the issue might be deeper especially if you’re dealing with large or multiple Mac Outlook (OLM) files. In such cases, it’s better to use an expert solution.
We recommend trying the CubexSoft Mac OLM Converter – a reliable utility to handle complex OLM file problems with ease. Here’s what makes it stand out:
- Free Demo Available – Try before you buy
- Mass Conversion – Convert multiple OLM files at once
- Multiple Saving Options – Export OLM to PST, PDF, MBOX, MSG, Office 365, IMAP, Gmail, and many more formats
- Simple Interface – User-friendly interface suitable for both beginners and experts
Whether you’re migrating data or resolving profile-related issues, OLM File Converter can simplify the process. Give the free demo a try and experience hassle-free Mac Outlook management!
