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Exchange Hybrid – The Unspoken Limitations That You Should Know

During the inaugural Microsoft Ignite conference, I was selected to present a “community theater” session; my session was titled “Exchange Hybrid – The Unspoken Limitations That You Should Know”.
The idea around this session was the we should always know the capability of a technology before deploying it into production. The earlier we can identify any limitations, the earlier we can communicate them to our project sponsors and end users. In some cases, communication is the only workaround necessary for the limitation, in other cases there are existing workarounds that can be helpful; I have identified some of these workarounds in the presentation slide deck below.

Session Description

Below was the published session description:

Session Summary

After a quick review of what Exchange Hybrid is and isn’t, the session focused on these 10 limitations:

  1. Cross-Premises Delegations
  2. Dynamic Distribution Groups
  3. Self-Managed Distribution Groups
  4. Address Lists
  5. Organizational Relationships with Other Orgs
  6. When “Single Sign-On” is not Single Sign-On
  7. ActiveSync Profile Conversion
  8. The Good and Bad of Directory Sync
  9. Third-Party SMTP Gateways
  10. Adding “Up-Level” Versions of Exchange


If you would like the slides from the presentation which includes some of the links to workarounds, I have made them available for download: JoePalarchio_Ignite_Presentation.pdf
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I am also speaking during an upcoming webinar with Centrify, “Proven Practices for Office 365 Deployment, Security and Management” on June 3 at 1 pm CT.  Hope you can join!

Thoughts on “Exchange Hybrid – The Unspoken Limitations That You Should Know”

  1. How do you deal with users that share their calendars only with other users? There is no way to determine before a user is moved if that user has a calendar shared with another user (who wont be getting moved). Using PS scripts we can see all shared mailboxes and delegate relationships and group those users together to mititgate those issues, but if a user simply grants another user rights to their calendar, and that calendar is then opened by that other user, there is no way we know of to see that. Either of those mailboxes get moved without the other one getting moved, then the cred pop ups begin.

  2. Joe Palarchio

    You can pull that delegate information via PowerShell (Get-MailboxFolderPermission) but it’s very time consuming and probably not realistic in an organization of any size.
    The reality is that you’re not going to be able to account for every user’s delegations that they may have. You do the best that you can by possibly looking at full access, send-as and send-on-behalf, you make sure the important people are taken care of as well as any shared mailboxes that may impact business processes. After that, just make sure you communicate well that users may experience temporary interruptions during the migration and batch users into their working groups and move users as fast as feasible.
    Thanks for the question.

  3. I really appreciate your response. Yes aware of the mailbox folder permissions commands, but agree just not feasible. We are in pilot phase of 20,000 mailbox Office 365 deployment and are concerned about calendar sharing. I figured you would respond how you did but just wanted to be sure there werent any other tools or options to help with this. Bottom line is this is just something we will have to deal with as an organization with good communication and make sure expectations are set beforehand.

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Joe Palarchio

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