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Xadean's Empirical Musing > Posts > Outlook 2016 Continuously Prompting for Password with AD FS 2012 R2, Web Application Proxy, and Office 365
October 23
Outlook 2016 Continuously Prompting for Password with AD FS 2012 R2, Web Application Proxy, and Office 365

Environment:

All users hosted on Exchange Online as part of Office 365 tenant subscription. Users are synchronized from on-premises Active Directory using Azure AD Connect. AD FS is implemented with Web Application Proxy. Users are using Outlook 2016 external to the corporate network.

 

Issue Description:

After launching the Outlook 2016 desktop client, users are continuously prompted to enter username/password.

 

Resolution:

Open Registry Editor by running "regedit".

Go to the following hive:

  • Exit Outlook
  • [HKEY_CURRENT_USER\Software\Microsoft\Office\16.0\Outlook\AutoDiscover]
    You must add these registry entries:

    "ExcludeScpLookup"=dword:00000001
    "ExcludeHttpsAutodiscoverDomain"=dword:00000001
    "ExcludeHttpsRootDomain"=dword:00000001
    "ExcludeSrvLookup"=dword:00000001
    "ExcludeHttpRedirect"=dword:00000000
    "ExcludeSrvRecord"=dword:00000001

  • Open File Explorer and browse to "C:\Users\<USERNAME>\AppData\Local\Microsoft\Outlook" (change <username> part to your specific settings) and delete the "[GUID] – Autodiscover.xml" files. Mine looked like this: "1f219c7c0fb9d245803b3872cb4da4ab – Autodiscover.xml".
  • Launch Outlook again.

The username/password prompts should cease.

 

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