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You modern authentication troubleshooting should always use NTLM over Basic authentication, as Basic sends the username and password in the clear, and NTLM is Windows Authentication. On Exchange 2013, you also have a new option called Negotiate, which is recommended. Please make sure you set both the ClientAuthenticationMethod to NTLM and IISAuthenticationMethods to Basic,NTLM (and Basic,NTLM,Negotiate for Exchange 2013 Now, let us start with the manual processes to fix Outlook syncing errors. Outlook and Office 365 sync issues can be frustrating but are almost always fixable. Start with basic network checks, enable Cached Exchange Mode, and repair your data files if needed. For persistent problems, rebuild your Outlook profile or use FixTechGuide’s free diagnostic tools to automate detection of authentication and IMAP errors in second You can set it to a higher number if you desire / need but it works for a user who has 14 mailboxes. The only other thing modern authentication troubleshooting that I experienced was the ‘bitness’ of some outlook plugins or their application via gpo. The next thing to check is the Virtual Directories and the Client Access Server Autodiscover URI and fix them accordingly too. All InternalUrl and ExternalUrl’s should be setup using the hostname mail.domain.com (assuming mail.domain.com is the OWA URL that you chose). You need to make sure your OutlookAnywhere and AutoDiscover settings are setup properly along with Split-DN Had my agenda only in the ost, so not synched to the webmail.After making a new profile my agenda items were gone. Used the Recovery tool for Outlook to restore the items to a PST from a backup of the old OST files. This worked modern authentication troubleshooting well although only the agenda item are restored, not the attachments and extra information field. The Microsoft Outlook Inbox repair tool includes an online version, found here. The Outlook Online Repair Service allows you to repair corrupted PST/OST files on any device (desktop, tablet, phone) with any OS (Windows, Android, macOS, iOS and so on This often happens because the cached DNS record is stale or incorrect. Flushing that cache wipes the slate clean, allowing your computer’s resolver to fetch the latest and most accurate IP addresses for websites. However, it’s worth noting some concerns from users on community forums regarding whether flushing the DNS could disrupt active connection Outlook may fail to synchronize changes stored in the OST file or retrieve information from the modern authentication troubleshooting mailbox server due to problems with the application, system, or Outlook OST data file. As a result, Outlook may fail to update the Inbox or Outbox email folder. Also, any email sent to you or sent from your Outlook client will not be received or delivered. However, you can follow the solutions discussed in this article to find the cause and resolve this issue in Outloo Outlook and third-party apps may conflict with each other, especially the security apps, such as antivirus, anti-malware, or firewall. If the antivirus program isn't Outlook friendly, you may experience certain issues while using Outlook. To check whether the antivirus app is preventing Outlook from updating the Inbox or Outbox folder, temporarily disable the antivirus program and restart Outloo In this scenario, when you try to add your Exchange Online email account to Outlook, the Modern authentication prompt goes blank after you enter your Exchange Online credentials. Therefore, you can't proceed to add the account to your default Outlook profile. This article contains information about how to troubleshoot problems that affect the ability to sign in to Microsoft Office 2016 apps and Microsoft Office 2013 apps that are enabled for modern authentication. This article also contains resources for IT administrators to address reports about Active Directory Federation Services (AD FS) issues that are specific to Office for Windows platforms. For convenience and time sake, I usually just disable modern auth in the registry and then I get the older Windows Security login box and the user put's in the password and the issue is resolved. Similar to Mac Mail, UO email accounts set up in iOS Mail application prior to the Modern Auth update will continue to work provided the device is running iOS 11 or newe This blog talks about the causes behind Outlook synchronization errors and a few solutions to fix Outlook sync issues. We have shared five manual methods in this blog to resolve the Outlook syncing errors. Apart from this, we also discuss the Shoviv OST to PST Converter Tool, a professional way to repair, recover, and convert Outlook data files. This solution will be beneficial for users who are facing Outlook syncing issues because of corrupted PST or OST files. Users can also try its free demo version in their system and process the first 50 items from each folder freel Before finding solutions, we suggest that users check their internet connection. Sometimes, Outlook sync issues can arise because of poor internet connection. If you are still facing this issue, kindly follow the solutions below to fix the sync issues in Outlook. There are various methods to resolve the Outlook sync issues, including manual and third-party solutions. Firstly, we will discuss a few manual methods to resolve this Outlook error and share the stepwise procedure of each method to successfully fix synchronization modern authentication troubleshooting issue