SOLVED! The Authentication Session Has Expired. Please Sign-In Again

Many Mac users are reporting “The Authentication Session Has Expired- Please Sign-In Again” error nowadays. If you have been dealing with the same, you have come across the right page. Millions of Mac users find Microsoft a convenient way to look over their personal and professional work. In this fair, we can say that you must be looking for genuine methods to resolve the error. So, here we have rounded up the best methods to fix it after checking all causes. So, let’s dive!

What Impact If The Authentication Session Has Expired- Please Sign-In Again Error on Users?

Outlook--Your session has expired - Microsoft Community

Mac users report this error when they are connecting to OneNote Mac, and the app tells them to log in again or sync their notes. After login, the message is repeated. However, this error is giving incompatibility to users to operate their files, which is annoying. Many users have already uninstalled and installed the application again to fix the issue, but it is popping. Besides, the alert can disappear when you enter details countless times. To solve your frustration, here we have come up with a few fixes. Let’s know. 

What Are The Causes Of The Authentication Session Has Expired- Please Sign-In Again Error?

While checking the error, we have investigated the causes first so we can give you the best results. Here are the few causes:

  • If the office is not accessing your Keychain
  • Interference of Microsoft user data 
  • Antivirus issue

How To Fix The Authentication Session Has Expired- Please Sign-In Again Error?

Fix: The Authentication Session Has Expired MS Office - AppleToolBox

After knowing the causes behind the error, we can find solutions that can help you fix the issue quickly. So, here is your guide. 

Method 1- Allow Office To Access Your Keychain

This error may occur because your office does not have access to your Keychain. 


  • Step 1– Sign out from your Microsoft office app and close it.
  • Step 2– Launch the keychain app.
  • Step 3– Choose the default keychain and click on the lock icon. Most probably keychain is unlocked. 
  • Step 4– Next, launch the official app you want to use and give Microsoft app to work on a keychain. 
  • Step 5– Make sure to enter the credential correctly and choose the always allow option to ease the work. 
  • Step 6– The office prompts you to sign in again and your credentials. Now check if the error persists or not. 

If the office still does not grant permission to use it, then choose method 2.

Method 2- Find Location In The Office Folder

If the office does not allow you to prompt the office even after granting access with Keychain. So, there will be an issue with the installation package, which may be moved to another folder. So, check the office package’s folder. If you have accidentally moved the folders, then the following steps can help you. 

  • Step 1– Locate the office folder and find where it moved. 
  • Step 2– Once you find the file, restore it to its original path.
  • Step 3– You can restore settings too.  
  • Step 4– Once done, restart your phone and see the error is fixed. 

Method 3- Eliminate Certain Password Entries

Sometimes one cannot be able to log in to the office if certain password entries exist. If this is your case, follow the given steps. 

  • Step 1- Log out all the office apps you are using.
  • Step 2– Again, launch Keychain and find the password entries you have worked on, such as Microsoft office identities cache two and Microsoft office identities settings 2. 
  • Step 3– If you see there are some ADAL entries in the Keychain, then delete all of them. 
  • Step 4- Restart your pc and launch the office again. 
  • Step 5– Sign in again. 

Method 4- Install/Renew Keychain 

Due to improper installation of Keychain, you might not fix the issue. So, here’s how you can do it. 

  • Step 1– Log out from all office apps.  
  • Step 2– Launch the finder and press command + shift G to start the go to folder window.
  • Step 3– Enter the library and tap on the go button.
  • Step 4– Now navigate the library/group/containers and remove the folder. 
  • Step 5– Next clear the keychains with the step:
  • Launch finder >> applications >> utilities >> keychain access.
  • Step 6– Find and delete all the Microsoft files and office entries. 
  • Step 7– Restart your PC and launch the office again. 

See if the error is fixed or not. If not, move to method 5. 

Method 5-Delete The Microsoft User Data Folder

If your system stored old files for a long time in the office, sometimes your Microsoft user data folder is the threat to having all issues. So, to fix it, find the given steps. 

  • Step 1– Find the documents directory and locate Microsoft user data.
  • Step 2– When you right-click and choose the delete option. 
  • Step 3- A pop-up menu will open to confirm the delete command. 
  • Step 4– Click delete and wait for a sec. 
  • Step 6– Restart your Mac and see the error is fixed.

Method 6- Turn Off Antivirus

After all the efforts, if you still persist in the error, then your antivirus protection may cause trouble to launch the file. So to fix it, you will need to turn off antivirus and see if the error is fixed. You can turn it off by locating antivirus protection and tapping on the turn-off button. 

Frequently Asked Questions

1\ What is Keychain?

It is a password management system on Mac developed by Apple to store various types of data, private keys, certificates, etc.

2\ What does The Authentication Session Has Expired- Please Sign-In Again error mean?

It is a type of error message that occurs when you’re not able to sync your Mac with Microsoft office.

3\ What is an office folder?

The office folder holds the number of data and files you have saved, created, and received for your work. 

Tips And Tricks

  • Reinstall the Microsoft office on Mac
  • Install the Keychain properly
  • Delete your old profile and create new

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