Why is My Mac Outlook Asking Password Again and Again?

 Are you wondering why is my Mac Outlook asking password again and again, even though you enter it correctly every time? You’re not alone, this is a common frustration for a lot of users. The good news is, there’s a simple fix to this problem. Whether you use Outlook on Mac or Windows, this guide will walk you through an easy and effective solution to stop those repetitive password prompts once and for all.

Why Does This Happen?

In most cases, the problem arises when Outlook has trouble verifying your account credentials. On Mac, a common reason behind this is a glitch in Keychain Access, which stores login details for your apps and services. If that data becomes outdated or corrupted, Outlook may struggle to fetch your saved password leading to repeated prompts asking you to log in.

But don’t worry, we’ve got a straightforward method to help you fix the issue and get Outlook working smoothly again.

What You’ll Learn?

In this post, we’ll write-up you step-by-step through repairing your Mac’s Keychain settings so Outlook can securely access your saved login information. By the end, you’ll be able to open your inbox without being hassled for your password every time.

Why Does Outlook Keep Asking for My Password on Mac? A Real User’s Experience

• Why does Outlook on my Mac keep prompting me to enter my password?
• How do I fix repeated password requests in Outlook for Mac?
• What causes Outlook to constantly ask for my password on macOS?
• How can I stop Outlook from asking for my password over and over on my Mac?
• Is there a way to permanently save my Outlook password on Mac to avoid repeated prompts?

Why Does Outlook Keep Asking for My Password on Mac? Here’s What’s Really Going On

Macs are well-known for their strong security and smooth performance, thanks in part to a handy tool called Keychain Access. This built-in password manager safely stores login details for various apps and services including Microsoft Outlook.

But sometimes, things don’t go as planned. Keychain Access can become corrupted or misconfigured after system updates, resets, or unexpected glitches. When this happens, it may create multiple conflicting authentication tokens for your Outlook account. These duplicates confuse the system during login.

Because of this, even if you enter the correct password, Outlook ends up stuck in a loop, repeatedly asking you to sign in. It’s not that Outlook fails to recognize your password—it’s that Keychain Access isn’t handling the saved credentials properly anymore. This issue is particularly common with Outlook 2011 and 2016 on Mac, where the app depends heavily on Keychain for authenticating users.

So, if you keep getting password prompts in Outlook on your Mac, the root cause is likely your Keychain. Fixing Keychain problems is usually the key to ending those endless password requests.

Why is My Mac Outlook Asking Password Again and Again? –Query Resolved

If Outlook 2016 on your Mac keeps asking for your password when connecting to Office 365, the issue is often caused by a corrupted Keychain Access. This can mess with how Outlook saves and retrieves your login details.

Follow these simple steps to clear out the problematic data and stop those annoying password requests:

1. Close Outlook Completely

Before you begin, make sure Outlook is fully closed. Quit the app to avoid any interference.

2. Launch Keychain Access on Your Mac

• Open Finder.
• Click the Go menu at the top and select Utilities.
• Double-click Keychain Access in the Utilities folder.
• Alternatively, press Command + Space, type Keychain Access, and press Enter.

3. Find and Delete Old Exchange Account Passwords

• Fill Exchange, in the Keychain Access search bar (top-right corner).
• Review the results and delete all entries linked to your Exchange account by right-clicking and selecting Delete.
• Keep deleting until all Exchange-related items are gone.

4. Remove ADAL Authentication Tokens

• Now search for adal in the same search bar.
• Select all items labeled like MicrosoftOffice15_2_Data:ADAL:.
• Press Delete or right-click and choose Delete.

5. Delete Microsoft Office Identity Cache Files

• Search for office.
• Locate and delete Microsoft Office Identities Cache 2 and Microsoft Office Identities Settings 2.

6. Exit Keychain Access

• Once all relevant entries are removed, close the Keychain Access app.

Simple Manual Fixes for “Outlook Keeps Asking for Password” on Windows

1. Clear Cached Passwords via Windows Credential Manager

Outlook might repeatedly ask for your password if it’s trying to use old or incorrect saved credentials. To fix this:

• Open Microsoft Outlook and Control Panel at the same time.
• In Control Panel, go to User Accounts > Credential Manager > Windows Credentials.
• Look for entries related to Outlook, MicrosoftOffice, or MS Exchange.
• Hit on each relevant entry and select Remove to delete the saved passwords.
• Once done, restart Outlook and enter your password when prompted. This time, it should save correctly.

2. Turn Off “Always Prompt for Login” Setting in Microsoft Outlook

If Outlook is set to always ask for login credentials, it will keep prompting even if the password is correct. To disable this:

• Open Outlook and click the File tab.
• Select Account Settings, then choose your Exchange account.
• Click Change, then select More Settings.
• Go to the Security tab.
• Deselect the box which says “Always prompt for logon credentials.”
• Click OK, then Next, and finally Finish.
• Restart Outlook to apply the changes. This should stop the repeated prompts.

3. Make a New Outlook Profile to Solve Corrupt Data

Sometimes, a damaged Outlook profile causes password issues. Creating a new profile can help:

• Open the Control Panel and click on Mail.
• Click Show Profiles.
• Pick Add, add a name for the fresh profile, and tick OK.
• Enter your email details and complete the setup by clicking Finish.
• Under “Always use this profile,” pick the fresh profile from the dropdown.
• Click Apply and OK.
• Open Outlook with the new profile. Password prompts should stop.

4. Reset MS Outlook Login Credentials in Credential Manager

You can remove outdated Outlook login credentials from Credential Manager to refresh your saved passwords:

• Open Control Panel and go to Credential Manager.
• Click on Windows Credentials.
• Find entries related to Microsoft Outlook or your email account.
• Click the arrow next to each entry and select Remove.
• Confirm the deletion if prompted.
• Repeat for all relevant Outlook entries.
• Restart Outlook and enter your credentials again.

5. Switch to NTLM Authentication for Outlook Anywhere

For remote access, setting Outlook Anywhere to use NTLM authentication can resolve password prompt issues:

• Open Outlook and go to the File tab > Account Settings > Account Settings.
• Select your Exchange account and click Change.
• Click More Settings and navigate to the Connection tab.
• Click Exchange Proxy Settings.
• Pick NTLM Authentication from the dropdown, under Proxy Authentication Settings,.
• Click OK, then Next, and finish the setup.

Wrapping Up

If you have gone through all the manual troubleshooting steps and Outlook still repeatedly asks for your password, the problem may be more complex, especially if you’re working with large OLM (Outlook for Mac) files. These files can sometimes become corrupted or difficult to manage, causing ongoing issues that manual fixes can’t resolve. In such situations, turning to a professional tool can save you time and headaches.

One highly suggested option is the BitData Migration OLM Converter for Mac & Windows OS, a powerful and dependable app to efficiently handle complicated OLM file errors. This Mac OLM Outlook Converter simplifies the process of repairing, converting, and managing your Mac Outlook mailbox data, ensuring smooth performance without constant login prompts or data loss. Its user-friendly interface, support for multiple file conversions, and ability to preserve data integrity make it an excellent choice for tackling stubborn Outlook issues that manual methods can’t fix.