Tags: Outlook, error, Outlook 2016 for Mac, 2011, ldap, outlook for mac, Outlook 2019 for Mac, categories, issue, known, reviewer, 17768. The Tennessee Department of Human Services (TDHS) announced Commissioner Danielle Whitworth Barnes will leave state government in mid-November after 16 years of service to the citizens of Tennessee to return. 1 day ago Tags: Outlook, error, Outlook 2016 for Mac, 2011, ldap, outlook for mac, Outlook 2019 for Mac, categories, issue, known, reviewer, 17768. The Tennessee Department of Human Services (TDHS) announced Commissioner Danielle Whitworth Barnes will leave state government in mid-November after 16 years of service to the citizens of Tennessee to return. This issue occurs in Outlook 2016 for Mac version 15.9 and later versions when Outlook performs an Autodiscover operation and tries to connect to a service endpoint whose expected name is not present on the server's Secure Sockets Layer (SSL) certificate. After going through the above solutions mentioned to fix outlook 2016 for mac crashes when replying to email issue, you will be easily able to fix this issue. Apart from this, if the manual solutions fail to solve Outlook 2016 For Mac crashes and doesn’t send e-mail issue, then you can try the OLM File Repair Tool. I don?t think that MS Outlook 2011 on MAC will be going work with MS Exchange 2003 or earlier. I recently found that MS Outlook 2011 make use of Exchange Web Services (EWS) that was not initiated in anticipation of Exchange 2007.
Are you looking for a solution to fix Outlook Mac keeps asking for credentials? If yes, then your search ends here as through this blog, I will be explaining some effective methods to resolve this issue. So, here we go.
Many at times it happens that when Mac Outlook users enter the credentials while making a connection with Office 365. It stops the authentication process and keeps asking for the password again and again.
This issue occurs in Mac Outlook because of corruption in the Keychain Access program. It is a default application in Mac and saves the information of email account login. So, whenever the issue arises in Keychain Access, Outlook 2016 for Mac Keeps asking for password office 365.
Why does Outlook 2016/2019 Asks for Password
It is evident from above that the reason behind this situation is Keychain Access password. Keychain Access is an inbuilt feature of macOS that store and saves all the Mac-based applications.
Due to unexpected reasons, Keychain Access can be easily damaged or corrupted and it will disturb the Mac users in several ways. Similarly, in Mac Outlook, multiple duplicate tokens will generate in Keychain. It will lead to a complex situation and confuse with the authentic credentials. As a result, it forgets the original password and keeps asking for it. That’s why Outlook 2016/2019 Mac keeps asking for a password.
Fix Outlook 2016 For Mac Keeps Asking Password of Office 365 Account
To troubleshoot this problem, you need to delete any cached passwords for your account, and also delete any authentication tokens from the keychain. To do this, follow the steps given below:
Outlook 2016 Mac Error 17997
- First of all, you need to quit Outlook and all other Office applications.
- Now, start Keychain Access by using one of the following methods:
- Click on the Finder application, click Utilities on the Go menu, and then double-click Keychain Access.
- Under Spotlight Search, type Keychain Access, and then double-click Keychain Access in the search results.
- In Keychain Access, enter Exchange in the search field.
- Under the search result, select each item to view the Account that’s listed at the top, and then click Delete. You have to repeat this step to delete all items for your Exchange account.
- Inside the search field, enter adal.
- Then, select all items whose type is MicrosoftOffice15_2_Data: ADAL:<GUID>, and then click on the Delete button.
- Under the search field, type office.
- After that, select the items that are named Microsoft Office Identities Cache 2 and Microsoft Office Identities Settings 2, and then click Delete.
- Now, Quit Keychain Access.
If you are not comfortable using Mac Outlook then you can Convert Mac Outlook OLM files to Windows Outlook PST in order to access emails on Windows.
Conclusion
As of now, you must be aware of the fact that Keychain Access is one of the dynamic features of mac OS. By using this, there is no need to remember each and every password. But due to the generation of some duplicate tokens in Key chain, Outlook Mac keeps asking for credentials. Hence, in this article, I have provided a method to resolve this issue. Hope it helps.
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Most of the Mac users complain about error messages in Outlook for Mac. The reason for error depends on the utilities in application, settings and network. If the Outlook for Mac is not synchronized with the server then the user gets error messages. These errors can be removed manually by following some easy techniques that help in quick revival of files and resolve Outlook for Mac synchronization issue. There is also an automated method available to fix the Outlook for Mac errors by using OLM Repair Tool.
However, It is advised to be prepared with manual methods as one can easily fix the problem at an instant time. Also, learning methods to fix Outlook for Mac errors prevent from spending money on Mac Recovery Software. Here are the methods by which OLM files can be repaired and recovered easily. Check out the causes and how to resolve them.
Causes of Outlook for Mac Error
- Error message: Cannot Find [Path name]OLM.DLL. This message is encountered when the file is moved or deleted.
- Error Message: Application failed to start as OLM.DLL is not found
- Outlook Error Code 17199
Each error code also shows a detailed message which makes it easy to solve the problem

- Not able to locate the file
- Action cannot be processed
- Access denied- can’t access email messages in Outlook
Outlook 2016 Mac Error Code 17997
Here are the methods which help in resolving general error methods
Update Outlook for Mac
The first and the foremost step to resolve any problem is to check for updates. If the application is not updated then it becomes incompatible with other utilities which result in an error. To update Outlook for Mac follow the below-given steps
- Open Outlook and then go to settings
- Check if there is any update available
- If yes, then download the update and install them
- Restart Outlook and the problem will be resolved.
This method will work out best if a user is facing ‘Outlook Opens and then Closes Automatically’ error.

Resolving ‘Outlook for Mac Synchronization Problem’

When the server and application cannot synchronize with each other then, the files will not be available in the application and it will halt the usage of Outlook for Mac. To, resolve this synchronize the OLM with the server or reset it.
- Start the Outlook for Mac application (if it is possible to open)
- Go to Menu, then select preferences and click on Sync Services
- Uncheck all boxes and Restart Outlook in Mac
- Reset the sync preferences to Fix Outlook synchronization problem
Use Microsoft Database Utility
The database utility is an application which gets installed when the Outlook for Mac is installed in the system. This tool can fix minor errors and repair OLM files easily.
- Go to drive where Outlook for Mac is installed
- Browse the location as Applications/ Microsoft Office 2011/ Office and then locate Microsoft Database Utility
- Launch the tool and select the option to scan
- Microsoft Database Utility will scan and repair the minor bugs/ corrupt OLM files
- Restart Outlook to see the problem is resolved
Clear Cache in Outlook for Mac
When synchronization between server and Outlook for Mac is interrupted due to network connection, power failure and other reason, the cache has incomplete files which result in an error. So, clear the cache to resolve the error
- Close the Outlook and other applications using it
- Go to Applications, Utilities and then Open Activity Monitor
- Type Sync to and quit all the actions and processes. After that close the Activity Monitor
- Browse to Home/ Library/ Application Support and launch Open SyncServices
- Delete files and move to trash, then restart the application and turn on Sync Services.
- The cache will be cleared and Outlook will start with fresh settings
By the above methods, you can fix the Outlook for Mac error messages and resolve synchronization problems.