Tag Archives: Outlook

Outlook with ADAL + Hybrid Modern Authentication causing a white box and AADSTS500011 / 500011 errors in Azure AD

We are in the process of selectively turning on ADAL for Outlook clients. We have already gone through enabling Hybrid Modern Authentication for Exchange (https://docs.microsoft.com/en-us/exchange/configure-oauth-authentication-between-exchange-and-exchange-online-organizations-exchange-2013-help) a while back. We recently ran into an issue where specific users were getting a white box about a minute after launching Outlook. I have seen this issue where all of Outlook freezes, but this was not the same. They receive this error while Outlook continues to run in the background. The error is also accompanied by an Azure AD sign-in failure for the user. The error received is 500011. When looking this up in the documentation (https://login.microsoftonline.com/error?code=500011) you can see it is referring to the error ‘The resource principal named {name} was not found in the tenant named {tenant}‘.

I decided to do a Fiddler trace to get to the bottom of this and this is where the issue started becoming clearer. In the trace you see Outlook reaching out to autodiscover.domainname.com (which is on-prem), getting a 401 response, reaching out to login.windows.net/login.microsoftonline.com, and looping in this manner. This part of the capture aligned exactly with the mysterious white box.

In my case this specific set of users had a different primary SMTP address (and UPN) than the other users we had already enabled ADAL for and their autodiscover.domain.com URL was never added to our Azure AD service principals for the ‘Office 365 Exchange Online‘ application ID. Microsoft documentation talks about this in Step 5 of the link I added at the beginning of this post. Using the ‘MSOnline‘ PowerShell module I was able to add the URL to the service principal list.

$x = Get-MsolServicePrincipal -AppPrincipalId 00000002-0000-0ff1-ce00-000000000000
$x.ServicePrincipalnames.Add("https://autodiscover.domain.com/")
Set-MSOLServicePrincipal -AppPrincipalId 00000002-0000-0ff1-ce00-000000000000 -ServicePrincipalNames $x.ServicePrincipalNames

After adding the principal there were no more instances of the white box.

Allow RSA SecurID token import via Outlook/Intune/MAM on iOS

One issue we ran into during our Intune/Outlook pilot for Android/iOS devices was the inability to click RSA SecurID token links used to import tokens. We will eventually be moving away from RSA, but in the meantime this was a challenge. I was able to come up with a workaround that allowed an import from Intune/Outlook into RSA SecurID while using MAM policies an iOS device.

  • In the MAM policy (Application Protection policy) that targets Outlook/Edge create a ‘Data Transfer‘ exemption for ‘com.rsa.securid
  • Email the RSA SecurID token to the user using the format: com.rsa.securid://ctf?ctfData=xxxxxxxxxxxxxxxxxxxxxx
  • Copy this link (be sure to not copy any spaces or) into Edge and hit ‘go

After hitting ‘go‘ Edge should prompt you to open up the token in RSA SecurID.

Creating group-based GPO without requiring a logoff/logon to take effect

As part of piloting O365 I was tasked with implementing hybrid modern authentication in our Exchange org in order to leverage functionality like the Outlook mobile application and MFA within the Windows version of Outlook for on-prem mailboxes. One caveat of enabling hybrid modern authentication in Exchange is that once this is flipped on any compatible client (ex. Outlook 2016) will begin using modern authentication (ADAL) exclusively by default. This switch can potentially be disruptive and we did not want to run into issues with the general user base. To do this we needed to disable modern authentication in Outlook on the client-side while being able to selectively enable it for certain users. This is easily handled with a ‘EnableADAL’ registry setting via GPO/Group Policy Preferences (GPP)/AD group. The issue is when you use an AD group with a group policy any member addition/removal needs to be coupled with a logoff/logon (or a reboot if it involves in a computer object in an AD group) to generate a new Kerberos token. I wanted to be able to quickly enable/disable ADAL for a user without requiring them to logoff/logon.

In order to get around this requirement I used GPP targeting with an LDAP query that looked for the group membership rather than standard group membership check. This LDAP query is completely dynamic and isn’t tied to the group list in user’s Kerberos token.

To do this you can do the following:

  • Create your GPP setting
  • Enable ‘Item-level targeting‘ on the setting
  • Create a new ‘LDAP Query‘ item
  • Create your filter using the distinguished name of your AD group and the ‘%LogonUser% variable
(&(objectCategory=user)(memberOf=GROUP DISTINGUISHED NAME)(sAMAccountName=%LogonUser%))
Create LDAP Query
Create LDAP Query condition
Retrieve group distinguishedName

This method could also be used for traditional GPO settings as well, but you’d have to use GPP to directly target GPO registry value(s) (ex. HKCU\Software\Policies\Microsoft\Windows\Control Panel\Desktop – ScreenSaveActive=0/1). This method could also be used for computer-based settings, but the LDAP query would have to be adjusted to target a ‘computerobjectCategory and the name of the computer (%ComputerName%). I wouldn’t use this method for everything, but can be very helpful for those one-off situations where you want a setting to take effect immediately without requiring a logoff/logon or reboot.