Tag Archives: Exchange Online

Send from Alias in Exchange Online

A bit later than planned, but I was attending a training last week, but a long-awaited feature in Exchange is sending mail from another email address that is stamped on a user, a so called alias. In a typical environment, a mailbox has a primary SMTP address and this address is used to send an receive email. This can be something like j.wesselius@exchangelabs.nl. Besides this primary SMTP address there can be more SMTP addresses that can be used to receive mail, for example Mr.Exchange@exchangelabs.nl or MasterOfDisaster@exchangelabs.nl. In Exchange on-premises and Exchange Online, these Aliasses are only used to receive email, not to send email. Up until now that is (for Exchange Online, no idea if they want to enable this for Exchange on-premises).

Microsoft has started to roll out the Send From Alias in Exchange Online starting in January 2022 (it was already announced back in April 2021) and it is available in Outlook on the Web and Outlook for iOS and Outlook for Android. Outlook for the PC will follow, according to Microsoft in Q2, 2022.

To enable the Send from Alias in Exchange Online, execute the following command in Exchange Online PowerShell:

[PS] C:\> Set-OrganizationConfig -SendFromAliasEnabled $True

It takes some time before effective, in my case it worked the next day.

All SMTP proxy addresses on a mailbox are available for this. When you logon as a user and go to settings | Mail | Compose and Reply you can check which aliases you want to use. + Addresses are also shown and so are the mail.onmicrosoft.com addresses. Don’t know who thought this was useful, in my opinion you don’t want to use these (internal) addresses at all:

Now when you write a new email in Outlook on the Web and select the From option, you can select the email address that you checked in the previous step.

The proxy addresses that are selected in the first step (the OWA settings) will automatically available in Outlook for Android and Outlook for iOS.

When you send an email using one of these aliases as a from address, it will automatically be visible in the recipient mailbox, in this example in Gmail:

I don’t expect much use of this feature until Outlook for the desktop will offer it, but it’s a nice add-on (finally).

Older Outlook versions will not connect to Office 365

it was already announced on the Microsoft blogpost New minimum Outlook for Windows version requirements for Microsoft 365, Microsoft will stop support for older Outlook clients on November 1, 2021 (which is 24 days from the time of writing!).

In short, all clients older than Outlook 2013 SP1 with the latest fixes are no longer able to connect to Exchange Online. And yes, this includes Outlook 2010 (I know there are still clients out there running Office 2010!).

More detailed version numbers of Outlook that will not connect anymore:

Office versionOutlook version
Office 2010All versions
Office 201315.0.4970.9999 and older
Office 201616.0.4599.9999 and older
Office 365 ProPlus1705 and older

To check the version of Outlook you are using, select File –> Office Account –> About Outlook. It will show something like Microsoft® Outlook® for Microsoft 365 MSO (16.0.14326.20384) 64-bit.

Please be aware that this is completely independent from the Basic Authentication strategy that Microsoft is following. Older versions will just stop connecting to Exchange Online.

For more information, check MC288472 in the Microsoft 365 Message Center.

Remove Exchange Hybrid Configuration

After decommissioning the Resource Forest I still have an Exchange 2016 environment on-premises, but all my mailboxes are in Office 365. Users are provisioned in Active Directory, Remote Mailboxes are provisioned in Exchange 2016 and everything is synchronized to Office 365 using Azure AD Connect.

Do I still need an Exchange Hybrid Configuration? Unless there are plans to move resources back to Exchange on-premises there’s no need for a Hybrid Configuration. To stay in a supported configuration, an Exchange server on-premises is still needed for management purposes, but only Azure AD Connect is needed and not a full hybrid configuration.

Note. If you want to use the on-premises Exchange server for SMTP relay purposes you don’t need the Hybrid configuration either. Just make sure you have a SMTP Send Connector that points to Exchange Online Protection and you’re good.

Removing the Hybrid configuration consists of the following steps:

  • Disable Autodiscover SCP in Exchange
  • Remove the Hybrid Configuration from Active Directory
  • Remove Connectors in Exchange Online
  • Remove the Organization Sharing from Exchange Online
  • Disable OAuth

Disable Autodiscover SCP in Exchange

When all Exchange resources are in Exchange Online you no longer need the on-premises Service Connection Points (SCP) for Autodiscover. But make sure you have the correct CNAME records for Autodiscover that point to Autodiscover.outlook.com.

To disable the SCP records in Active Directory, execute the following command in Exchange Management Shell:

Get-ClientAccessServer | Set-ClientAccessServer -AutoDiscoverServiceInternalUri $Null

Remove the Hybrid Configuration from Active Directory

Removing the Hybrid Configuration from Active Directory is just one PowerShell command in Exchange Management Shell:

Remove-HybridConfiguration -Confirm:$false

There’s one pitfall here, this will also remove the outbound to Office 365 Send Connector from Exchange. If you want to keep SMTP relay from on-premises to your mailboxes in Exchange Online you have to manually recreate this connector (use yourdomain-com.mail.protection.outlook.com as a smarthost for this)

Remove Connectors in Exchange Online

In the Exchange Online Admin Center, remove the outbound SMTP connectors that point from Exchange Online to your on-premises Exchange organization. If you want to keep SMTP routing, keep the inbound SMTP connector, otherwise you can remove this as well.

Remove the Organization Sharing from Exchange Online
To remove the Hybrid Organization Sharing from Exchange Online navigate to Organization | Sharing in the Exchange Admin Center and remove the organization sharing.

Disable OAuth on-premises

When used before you can disable the OAuth configuration as well from Exchange on-premises and Exchange Online.

In Exchange on-premises Management Shell, execute the following command:

Get-intraOrganizationConnector | Set-IntraOrganizationConnector -Enabled $False

And to do this in Exchange Online Management Shell, execute the following (same) command:

Get-IntraorganizationConnector | Set-IntraOrganizationConnector -Enabled $False

These are the steps needed to remove the Hybrid Configuration from your Exchange environment.

Note. Microsoft recommends to leave the Exchange Hybrid option in Azure AD Connect.

Summary

In this blogpost I explained how to remove the Hybrid Configuration from your Exchange environment after you have moved all resources to Exchange Online.

The on-premises Exchange server is still needed for management purposes. After removing the Hybrid Configuration you can still manage your recipient Exchange Online using the on-premises Exchange server, all changes are replicated through Azure Active Directory.

Is that last Exchange server on-premises still needed? Yes, you need it for managing your recipients in Exchange Online. When you have Azure AD Connect running in your environment, the objects are managed in on-premises Active Directory. The source of authority is Active Directory. As long as Microsoft hasn’t fixed the source of authority problem, an Exchange server on-premises is still needed.

Exchange 2016 End of (mainstream) support

As you should (must) know, Exchange 2010 support will end this October. At that point, Microsoft will stop all support for Exchange 2010, including all security fixes. If you are still running Exchange 2010, you must act now and start moving to Exchange 2016 or to Office 365. For an Exchange 2010 to Office 365 migration I have written a couple of blogs before:

Moving from Exchange 2010 to Office 365.

Moving from Exchange 2010 to Office 365 Part II.

But what most people don’t realize is that Exchange 2016 mainstream support will also end this October. From that point forward, Exchange 2016 will be in extended support. This means no more Cumulative Updates and only Security Updates will be released when there updates are marked as ‘critical’.

Note. There’s no direct upgrade path from Exchange 2010 to Exchange 2019, so if you want to follow this route, you must move to Exchange 2016 first, followed by a migration to Exchange 2019.

If you move to Office 365 and have moved all your Mailboxes to Exchange Online, things are getting interesting. In this situation, you still need at least one Exchange server on-premises for management purposes. Microsoft supplies a free Exchange 2016 hybrid license for this situation (there is no free Exchange 2019 hybrid license!), and Microsoft is committed to support this configuration. At least until the moment a final solution is delivered by Microsoft to remove that last Exchange server from your on-premises organization. According to Microsoft, “this does not increase your risk profile in any way” as stated in their article “Exchange Server 2016 and End of Mainstream Support”.
If you still have mailboxes on-premises, the Microsoft recommendation is to move to Exchange 2019. Mainstream support for Exchange 2019 will end on January 1st, 2024, and extended support for Exchange 2019 will end on October 14, 2025 (this is the same date as end of extended support for Exchange 2016).

What to do

  1. If you are still on Exchange 2010, I would urge you to move to Exchange 2016 as soon as possible. Mainstream support for Exchange 2016 will stop this October, but according to Microsoft you are still safe since Security Updates will be released when needed. There’s no direct need to upgrade to Exchange 2019 at this moment, but this is something you must consider the upcoming time. I do know customers however that only want products that are in mainstream support, so if you are in this boat you must move to Exchange 2019 of course.
  2. If you are running Exchange 2013, you must start moving to Exchange 2019 anytime soon for optimal support and skip Exchange 2016.
  3. If you are in an Exchange 2016 hybrid scenario and all your mailboxes are in Exchange Online, you are safe to stay in this situation until Microsoft releases a final solution for that dreaded last Exchange server on-premises for management purposes.

New Exchange Online PowerShell v2

When using PowerShell with Exchange Online you can use the ‘good old traditional’ way to connect to Exchange Online:

$ExCred = Get-Credential 
$Session = New-PSSession -ConfigurationName Microsoft.Exchange -ConnectionUri https://ps.outlook.com/powershell/ -Credential $ExCred -Authentication Basic -AllowRedirection
Import-PSSession $Session

This is not a recommended way to connect to Exchange Online using your tenant admin account, it uses basic authentication (will be decommissioned in 2021) and MFA (number one prerequisite for tenant admin security!) is not possible.

The second option is the Exchange Online Remote PowerShell Module which you can download from the Exchange Online Admin Center (use Internet Explorer for this download!) as shown in the following screenshot:

Exchange Online PowerShell Module

This is a separate PowerShell module you can start and use the Connect-EXOPSSession command to connect to Exchange Online. This PowerShell module users Modern Authentication and supports Multi-Factor Authentication.

The latest (and newest) option is the Exchange Online PowerShell V2 module. This module works far more efficient with large datasets than the previous PowerShell modules for Exchange Online. It also supports Modern Authentication and Multi-Factor Authentication.

To install the Exchange Online PowerShell V2 module you first have to install the PowerShellGet module using the Install-Module PowershellGet command:

Install-Module PowershellGet

Followed by the Install-Module -Name ExchangeOnlineManagement command:

Install-Module ExchangeOnlineManagement

When installed you can use the Connect-ExchangeOnline command to connect to Exchange Online. When MFA for your admin account is configured it will automatically use it:

Connect-ExchangeOnline

The differences between V1 and V2 are clearly visible in the commands. All V2 commands contain EXO, like:

  • Get-Mailbox vs Get-EXOMailbox
  • Get-Recipient vs Get-EXORecipient
  • Get-MailboxStatistics vs Get-EXOMailboxStatistics
  • Get-CASMailbox vs Get-EXOCASMailbox

This means that all scripts you have written for use with Exchange Online need to be changed to reflect the V2 commands.

For a complete overview you can use the Get-Command *EXO* to retrieve all PowerShell commands that contain EXO (still very limited 🙂 ):

Get-Command EXO

The Exchange Online PowerShell V2 module is still in preview, the current version is 0.3582.0 which you can check using the Get-Module ExchangeOnlineManagement command:

Get-Module ExchangeOnlineManagement

The Exchange Online PowerShell v2 module is a work in progress, but it the future of PowerShell in Exchange Online, so you should keep an eye on this development.

More Information

Use the Exchange Online PowerShell V2 module – https://docs.microsoft.com/en-us/powershell/exchange/exchange-online/exchange-online-powershell-v2/exchange-online-powershell-v2?view=exchange-ps