Tag Archives: Last Exchange Server

The last Exchange server in the organization

Many organizations struggle with that Last Exchange Server (LES) in the organization. All their mailboxes are in Exchange Online, but an on-premises Exchange server is still needed for managing the mailboxes in Exchange Online since the Source of Authority (SOA) is still the local Active Directory.

On August 21, 2025 Microsoft announced the Cloud-managed remote mailboxes. Mailboxes in Exchange Online with an on-premises Active Directory and Exchange server can now be fully managed in the Exchange Online Admin Center (or Exchange Online PowerShell) and an on-premises Exchange server is no longer needed for management purposes.

In the current situation the SOA is on-premises. A user object or mailbox is edited on-premises, and the complete object is synchronized with EntraID. From there, a forward sync mechanism sends the Exchange specific attributes to Exchange Online. Be aware that the forward sync normally takes only a few seconds, but occasionally it can take hours. This is shown in the following figure:

In the new situation, the user object is still in Active Directory and the remote mailbox in Exchange Online. Microsoft introduced a new property in EntraID called IsExchangeCloudManaged. Simply put, this breaks the synchronization of Exchange attributes and the user object in Entra ID, and the mailbox in Exchange Online can now be managed online. This is shown in the following figure:

There are a few gotchas, though:

  • The solution is available, but it is in Public Preview. This means that Microsoft can change it at any time, or even withdraw it at any time (I don’t expect this to happen, unless serious problems arise).
  • It is on a per-user basis, so the IsExchangeCloudManaged property must be set on every mailbox. This can lead to organizational chaos if you have mailboxes in both environments.
  • The Exchange properties still exist in Active Directory. They can be edited in Active Directory, but they are not synchronized with EntraID. As such, Exchange Online and Exchange Server can become out of sync, resulting in strange issues, especially when it comes to cross-premises mail flow.
  • An organization-level setting to make all newly synced users’ Exchange attributes cloud-managed is expected soon (September 2025).
  • This is an attribute-level SOA change. This means you can only edit Exchange-specific attributes in the online Admin Centers, but you cannot delete a synchronized account, for example.

Phase two of the IsExchangeCloudManaged implementation will contain write-back support for specific Exchange attributes from Exchange Online to Exchange server. It is unknown yet when phase 2 will be released and what specific attributes will be synced back.

A gotcha in phase 2 is that this will only be available in EntraID CloudSync, and not in EntraID Connect. Please note that phase 1 does support EntraID Connect, so there’s no immediate need to move to EntraID CloudSync because of this new feature.
As mentioned before, this is an attribute-level SOA change. Microsoft is also working on an object-level SOA change, where an entire object SOA is moved to the cloud. Microsoft recently released this for Groups, but for contacts and users this is still in the planning.

Enable the IsExchangeCloudManaged feature

To enable this new feature, you must use EntraID Cloud Sync version 2.5.76.0 or higher, see my previous blog about upgrading to this version. This version will prevent error when trying to sync Exchange attributes to EntraID when the IsExchangeCloudManaged attribute is set to $True.

Logon to Exchange Online PowerShell and request a list of mailboxes in Exchange Online with the IsExchangeCloudManaged attribute, as shown in the following example:

PS C:\> get-mailbox | select Name,IsExchangeCloudManaged

Name                                                         IsExchangeCloudManaged
----                                          ----------
jaap                                          False
DiscoverySearchMailbox{D919BA05-46A6-...}     False
Labs | TLSReports                             False
Jan Aart Wesselius                            False
Labs | Dmarc Reports                          False
Labs | Jaap Wesselius                         False
Labs | Errol Brown                            False
DMARC Reports Exchangelabs.nl                 False

The user Errol Brown is created as a regular user with a (remote) mailbox, so the Exchange properties are not populated in Active Directory. It is synchronized using EntraID Connect and has an Office 365 E5 license assigned to it.

Use the following example to set the IsExchangeCloudManaged attribute to true to enable the EAC in Exchange Online to manage this mailbox:

Set-Mailbox -Identity e.brown@exchangelabs.nl -IsExchangeCloudManaged:$TRUE

After some time, you can use Exchange Online PowerShell or the Exchange Online Admin Center to add for example, an e-mail address to this user:

Set-Mailbox -Identity E.Brown@Exchangelabs.nl -EmailAddresses @{add="Errol.MyMan.Brown@Exchangelabs.nl"}

This only relates to Exchange Online properties. When you want to change identity properties, for example, a first name or last name, it will generate an error. This must still be managed on-premises and is something that will be fixed in a future update.

More Information

H1 2022 Cumulative Update Exchange 2019 (CU12)

Last week, on April 20, Microsoft released Cumulative Update 12 for Exchange 2019 and Cumulative Update 23 for Exchange 2016.

It took Microsoft six month for the Cumulative Update, that’s because Microsoft is changing from a quarterly release cycle to a bi-annual release cycle. As a result, this will the Cumulative Update of the first half of 2022, so H1 2022 Cumulative Update.

This is only true for Exchange 2019 as there will be no new Cumulative Updates for Exchange 2016 anymore. Exchange 2016 has entered extended support, so Microsoft will deliver Security Updates when needed, but not more CUs. Mainstream support for Exchange 2019 will end on January 9, 2024 and extended support for Exchange 2019 will end on October 14, 2025. This is the same date as for Exchange 2016. What will happen then is still unknown….

Exchange 2019 CU12 now has support for Windows 2022 (finally). Support for Windows 2022 is only true for Exchange 2019 CU12, Exchange 2016 is only supported on Windows 2016.

When it comes to Active Directory, only Exchange 2019 CU12 supports Windows 2022 Domain Controllers. Exchange 2016 and Exchange 2013 do not support Windows 2022 Domain Controllers (despite earlier communication from Microsoft). For more information regarding supportability check the Exchange Supportability Matrix.

One of the new features of Windows 2022 is support for TLS 1.3 and several of my clients have a requirement for this. Unfortunately, Exchange 2019 still does not support TLS 1.3 and support for TLS 1.3 is expected by the end of this year.

With the new Cumulative Update comes a change in (free) licensing. Previously, there was a free license for the ‘hybrid server’ but this was Exchange 2016. Now with Exchange 2016 in extended support and no more CUs for Exchange 2016, the free hybrid license is available for Exchange 2019!

A lot of noise regarding the “remove the last Exchange server” in your organization. When you have all mailboxes in Exchange Online and you have Azure AD Connect running, you need to have one Exchange server, just for management purposes. This is no longer required with Exchange 2019 CU12. You can install the management tools for CU12 and get rid of the Exchange server. Be aware that you must NOT UNINSTALL the Exchange server, but clean up the hybrid configuration using PowerShell, shutdown the Exchange server and run the CleanupActiveDirectoryEMT.ps1 script (released with Exchange 2019 CU12).

Are there reasons to not do this? Yes, think about SMTP relay from on-premises to Exchange Online, or RBAC on-premises (not available with only the Management Tools on-premises), or maybe an offloading possibility when needed. Oh, and if you are not good with PowerShell, be aware that this is a PowerShell only solution. If you are addicted to the Exchange Admin Center, leave the Exchange server running 😉

But nevertheless, it’s good that Microsoft finally heard this feedback and offers a solution for the last Exchange server when all mailboxes are in Exchange Online.

A couple of remarks:

  • Be aware that Microsoft only supports the two latest CUs, i.e. Exchange 2019 CU11/CU12 and Exchange 2016 CU22/CU23.
  • There are no schema changes in these Cumulative Updates, but there are changes in the configuration, so you need to run setup with the /PrepareAD switch.
  • When running a Database Availability Group, do not forget to put the Exchange servers in maintenance mode.
  • As always, test the new CUs in your test environment before installing in your production environment.

More information and downloads:

Exchange versionKB ArticleDownload
Exchange 2019 CU12KB5011156https://www.microsoft.com/en-us/download/details.aspx?id=104131
Exchange 2016 CU23KB5011155https://www.microsoft.com/en-us/download/details.aspx?id=104132
Exchange 2016 CU23 language packshttps://www.microsoft.com/en-us/download/details.aspx?id=104130