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.
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
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 ‘computer‘ objectCategory 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.
We recently made changes to our on-prem Exchange org. Not long after we realized that any email flowing through Exchange Online to on-prem was not getting processed by our journaling configuration (per-database journaling). After digging and opening a case with Microsoft we found that Exchange Online was injecting this header:
This header tells Exchange that journaling was already processed. On-prem Exchange will then not process any journaling for that message. O365 apparently started injecting this header in the summer of 2018. The reason we did not run into the issue earlier is because until we were in hybrid mode (and ran the hybrid wizard) the Exchange header firewall was stripping this header as it arrived on-prem. They did release an article on this exact issue back in July 2016, but we didn’t come across it until Microsoft found the issue. The current fix is to duplicate all journal rules/settings in Exchange Online. According to Microsoft they are planning to add a warning in the hybrid wizard for this condition.
I recently started looking into using the Test-Mailflow cmdlet to develop an email flow monitoring script in LogicMonitor. I had never tried using it in my current environment before and when I tried executing the cmdlet it just timed out with this output:
I tried adding -Verbose and -Debug switches and did not get anything useful. I checked to make sure all system mailboxes (Get-Mailbox -Arbitration) were in place and verified the test messages were going out via the transport logs. I dug a little more into how the cmdlet actually works and found that it sends an email with a delivery receipt which led me to look into that. I eventually found that we had our ‘DSNConversionMode‘ set to ‘DoNotConvert’ in our transport configuration:
After changing it back to the default (UseExchangeDSNs) the cmdlet started working. During testing I was sending email from my mailbox to a system mailbox with the ‘Request a Delivery Receipt‘ option checked. Exchange is expecting the default format in the delivery receipt DSN email and when it is modified Exchange cannot process it.
Delivery receipt with DSNConversionMode set to DoNotConvert:
Delivery receipt with DSNConversionMode set to UseExchangeDSNs:
We recently went through some Exchange Online Protection (EOP) cleanup and part of that involved turning on Directory Based Edge Blocking. We already went through the exercise of syncing all objects (especially ones part of Exchange), but the only ones that weren’t being synced were mail-enabled public folders. After turning on Directory Based Edge Blocking we realized there were a few public folders that needed to receive mail from the Internet. After syncing mail-enabled public folders (this is a newer feature in AD Connect) we received synchronization errors for four objects. The only thing these objects had in common was that they referenced a mail-enabled public folder by either having that object as a group member or having it as a forwarding object on a mailbox.
The errors we receiving were:
The cause of the error is not clear. This operation will be retried during the next synchronization. If the issue persists, contact Technical Support.
The workaround is to create a mail contact object that has the same targetAddress as the mail-enabled public folder object and use that object in place of the public folder object in something like a group membership. The issue with this is that by design a mail contact’s targetAddress is also part of its proxyAddresses attribute and the mail-enabled public folder object of course already has the email address as part of its proxyAddresses attribute. This duplicate is not allowed. The way around this is to modify the mail contact object so that the targetAddress is not part of proxyAddresses. To create this special mail contact you do the following:
Create a mail contact in Exchange with a fake external address
Disable e-mail address policy for the object
Use ADSIEdit to:
Change the targetAddress to the email address of the mail-enabled public folder
Remove the fake external address you specified earlier from proxyAddresses
After the object has been created you can now use it in lieu of the mail-enabled public folder in group memberships and other attributes.