Tag Archives: Outlook

Properly securing your on-prem Exchange 2016 environment when using Hybrid Modern Authentication

In the past many organizations completely blocked or limited external access to on-premises Exchange servers because of the lack of multi-factor authentication. Protocols like OutlookAnywhere (also known as RPC-over-HTTP, now MAPI-over-HTTP) and EWS had no native methods to accomplish multi-factor authentication. Failure to protect these protocols from external exposure has led to many breaches like FIN4 and London Blue.

HMA to the rescue… In 2017 Microsoft finally answered this deficiency with Hybrid Modern Authentication. I briefly touched on modern authentication in two previous articles (here and here). With Hybrid Modern Authentication Microsoft gave you the ability to use new technologies like modern authentication and conditional access for on-premises Exchange. Clients will connect using modern authentication by default once Exchange is on a supported version, supported clients are implemented, and the configuration is implemented. The issue here is that legacy Windows authentication is still available. You can simply disable modern authentication in the client or use a different client and you are now connected to on-premises Exchange with a simple username and password completely bypassing conditional access. Conditional access is only invoked when you are authenticating with modern authentication. Exchange 2019 implemented Authentication Policies which allow you turn off legacy authentication methods. If you are using Exchange 2019, you can use these to lock down your environment.

We were in the situation where we wanted to allow secure external access to Exchange (mainly for OutlookAnywhere, but also Outlook Mobile), but we couldn’t have any legacy authentication exposure. The solution we came up with was creating a set of externally facing Exchange 2016 mailbox servers (think Client Access Servers from the pre-Ex2016 days) that have all legacy authentication methods disabled (only OAuth available). These servers are the only ones exposed to the internet. The protocols we want to expose but lock down are ActiveSync (needed for Outlook Mobile), EWS (Exchange Web Services), MAPI, and OAB (Offline Address Book). To lock these down we ran the following against the externally facing servers:

$Servers = @(Get-MailboxServer excas01)
$Servers = $Servers + (Get-MailboxServer excas02)
$Servers | Get-ActiveSyncVirtualDirectory | Set-ActiveSyncVirtualDirectory -BasicAuthEnabled $false
$Servers | Get-WebServicesVirtualDirectory | Set-WebServicesVirtualDirectory -WindowsAuthentication $false
$Servers | Get-MapiVirtualDirectory | Set-MapiVirtualDirectory -IISAuthenticationMethods @('OAuth')
$Servers | Get-OabVirtualDirectory | Set-OabVirtualDirectory -WindowsAuthentication $false

After this is completed, Windows and basic authentication should now fail for these virtual directories.

IMPORTANT: It is VERY important to regularly check that these settings are still in place. You should always re-run these commands after any kind of Exchange update. If you do not do this, you could inadvertently expose your Exchange environment. A simple script could be run on a schedule to check and report on any changes to the authentication configuration of these virtual directories.

The second step is disabling or blocking the other virtual directories that do not need to be accessed externally. For us, these were ECP, OWA, PowerShell, and RPC. We have an on-premises load balancer with SSL bridging configured for our Exchange environment, so we used that to block access to these virtual directories. Another option is to use IP restrictions in IIS on these virtual directories. A third option is to disable the virtual directories via PowerShell. For those of you who want to allow secure access to OWA (Outlook Web Access) you can use Azure App Proxy to accomplish this or an ADC like NetScaler or F5 Big-IP.

The final step in this configuration is allowing the O365 servers to reach an unaltered version of EWS for the IntraOrganizationConnector used for Exchange Online to pull free/busy data (and other data like photos) from your on-premises environment. I found that for some reason the IntraOrganizationConnector fails to authenticate from EXO->on-premises when it uses the modified virtual directory even though all OAuth tests pass. I also use this configuration for my MRS endpoint when doing mailbox migrations since MRS wants to do traditional Windows authentication to EWS. If you are using the Microsoft Hybrid Agent, you shouldn’t have to do this since Azure App Proxy is taking care of the MRS and free/busy communication. I have still have an ongoing ticket open with Microsoft to understand the root cause of this. The workaround is fairly simple:

  • Create a namespace that can be used for EXO->on-premises communications. (Ex. exocomm.domain.com)
  • Configure this namespace to point to your regular INTERNAL and unaltered mailbox servers
  • Lock down this namespace in your firewall, so that ONLY Microsoft O365 servers can reach it. NOTE: This is very important and failure to do so will undermine all of the work done above and leave you exposed. We use a combination of PaloAlto firewalls and MineMeld to accomplish this, but this can be accomplished with a static/maintained ACL as well.
  • Configure the IntraOrganizationConnector in EXO to not use Autodiscover and to use this new namespace as its endpoint with the following commands:
Get-IntraOrganizationConnector | Set-IntraOrganizationConnector -TargetSharingEpr "https://exocomm.domain.com/ews/Exchange.asmx"
Get-IntraOrganizationConnector | Set-IntraOrganizationConnector -DiscoveryEndpoint $null

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.