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Exchange Hybrid Report: Common Pitfalls in Recipient Management

Recipient Management can be challenging, especially in Hybrid Environments. The classic's are starting with not using Exchange Management Tools and instead solely relying on Active Directory management tools, which is not supported by Microsoft. Further into mutations there are other cases, like switching Mailbox types to or from Shared Mailboxes. There is surely not always a direct impact, over time however we can mostly see many of them.

  • Have you ever run IdFix in your environment, and which findings are you aware of?

Common Pitfalls

Shared Mailbox:

In hybrid environments, changing the mailbox type of a migrated mailbox needs to be done on both sides: Set-Mailbox in Exchange Online and Set-RemoteMailbox in on-premises Exchange.

  • Misalignment may result in unexpected licensing behavior or confusion during mailbox modifications.
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# Fix
Set-RemoteMailbox -Identity <mailbox ID> -Type Shared # On-Prem
Set-Mailbox -Identity <mailbox ID> -Type Shared # Cloud

RemoteMailbox:

User doesn't have the mail, mailNickName, or proxyAddresses attribute set. With an Exchange Online license, it sets the primary SMTP address by using the UPN.
User doesn't have the mailNickName or proxyAddresses attribute set. With an Exchange Online license, it sets the primary SMTP using the same value of the mail attribute.

  • E-Mails sent via the Exchange SMTP relay may not reach their destination.
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# Fix
Enable-RemoteMailbox -Identity <mailbox ID> -RemoteRoutingAddress "<mailbox ID>@contoso.mail.onmicrosoft.com" # On-Prem

Hybrid Report

Invoke-ModernMailHybridReport provides insights into common recipient misconfigurations and overlooked issues in hybrid Exchange environments. It gives you a structured overview and helps identify inconsistencies in mailbox settings, licensing, and user attributes.

Overview (How does it look)

The report is generated as a HTML file with grouped sections for Exchange Online and Exchange Server objects. It highlights important settings, unusual configurations or potential risks and making it easier for admins to spot and address common pitfalls.

Exchange Hybrid Report

Features

Attached a list of situations which i have seen in the past and may require attention, depended on your environment:

Description Exchange Online Exchange Server Recommendation
Regular Mailboxes which are Unlicensed Supported N/A Should be fixed
Shared Mailboxes which are Enabled Supported N/A May disable
Shared Mailboxes which are Licensed Supported N/A May required
Mailboxes with LitigationHold Supported N/A May verify
Mailboxes with Disabled AuditLog Supported N/A May enable
Distribution List with External Sender Allowed Supported N/A May disable
Mailboxes with unfavourable UPN (Idfix) Dependency Supported Should be checked
Mailboxes with unfavourable RecipientType (RemoteRoutingAddress) Dependency Supported Should be checked
Mailboxes with Retention Policy Gap's Supported N/A Should be fixed

Usage (Get Started)

You can install the PowerShell module and generate the report, with just a few commands. You'll receive a HTML overview of your hybrid recipients.

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# Install
# > Install the module from the PowerShell Gallery
Install-Module -Name ModernMailTools

# Run Report
Invoke-ModernMailHybridReport -OutPath "C:\Reports\ExchangeHybridReport.html"

Documentation

Explore the full documentation for usage scenarios and parameter references:

Summary

Managing recipients across Exchange Online and Exchange on-premises environments can be complex.
The Invoke-ModernMailHybridReport helps you uncover misconfigurations or potential design issues. I will surely add more features in the future and fix existing bugs.

Wishing you a great week!

References:

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