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What should I do when something goes wrong with my hybrid mailbox?

TomCruise-7376 0 Reputation points
2024-07-16T17:11:02.7266667+00:00

Our setup is as follows: Site0: Exch00 - Original On-Prem Exchange server. CAS, MBX, and all transport roles. Was not configured to perform any hybrid/management work with 365. DC0 - Site local DC to site where Exch00 is

Site1: Exch01 - Hybrid server, all 365 management etc. MBX, CAS, contains resource mailboxes and mailboxes to be exported to PST or migrated to 365. DC1 - Site local DC for Exch01 Client computers

Sites2-5: client computers, local DCs.

External sites: lots of offices that are not AD integrated and are using Outlook Anywhere.

365 - Setup with dirsync, not ADFS

Site 0 has failed, and does not need to be recovered. All user and resource mailboxes and other user data that was needed has already been migrated from those servers, and the site was set to be decommissioned properly at the end of the month. However, a hardware failure has taken care of that for us. We can restore from backup if needed, but since we're just going to be restoring to decommission I'd rather avoid that if possible.

We are currently having issues with Equipment calendars (but not Rooms) not being available. They are all stored in the same database, on the same server. All other calendars are functioning properly, it's just Equipment mailboxes which aren't working.

In Site1 Outlook is prompting for a password constantly but is functioning regardless of if the password is entered or not. Users in the external sites are not experiencing this issue.

Prior to the hardware failure last night, everything was working properly even though all Exchange services were disabled on Exch00. The DC has already been removed from AD Topology via ADSIedit, and there are no traces of it in our KCC. The site still exists in ADS&S I have the following questions:

Can I remove all traces of Exch00 via ADSIedit, as I would any other failed Exchange server, or are there additional concerns because of the 365 tie in?

Is there a separate arbitration mailbox that's used for Equipment mailboxes than there is for Rooms? If so, is there a proper process for recreating this arbitration mailbox? If not, is it likely that the problems with the Equipment mailboxes will be resolved once Exchange has updated topology information?

What could be causing the Outlook password prompting? The DC in Site1 is fully functional as is Exch01. Sites2-5 are also having the same password prompting issue.

Microsoft Exchange Online
Microsoft Exchange Hybrid Management
Microsoft Exchange Hybrid Management
Microsoft Exchange: Microsoft messaging and collaboration software.Hybrid Management: Organizing, handling, directing or controlling hybrid deployments.
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  1. Xintao Qiao-MSFT 1,560 Reputation points Microsoft Vendor
    2024-07-17T09:25:20.75+00:00

    Hi, @Tom Cruise

    It sounds like you are dealing with a complex Exchange and Office 365 hybrid environment. As a result, troubleshooting can be painful and time-consuming.

    Here are some suggestions for you:

    1.You can remove traces for Exch00 through ADSI edit, similar to how you would remove other failed Exchange servers. However, you need to be very cautious because of the Office 365 hybrid setup. Specifically:

    -Ensure that all necessary data and configurations have been moved or copied to Exch01.

    -Verify that any connector, mail flow, and AD attributes related to the hybrid setup do not depend on Exch00.

    2.In Exchange, arbitration mailboxes are used to manage approval workflows and are typically not set up separately for equipment mailboxes and room mailboxes. It is recommended that you prioritize updating the Exchange topology information to detect whether the problem is resolved. If the issue is not resolved, it may be that the arbitration mailbox is causing the problem with the equipment mailbox, at which point you can recreate it.

    3.The problem of Outlook constantly prompting for password can be caused by several factors:

    -Clear the cache. Old cached credentials can cause conflicts.

    -Outlook profile is corrupted. Sometimes creating a new profile may work.

    -DNS and network connectivity. Confirm that the DNS records are updated and there are no delays.

    -Autodiscover issues. Ensure that the Autodiscover service is configured correctly and points to the correct server.

    -Considering that it works regardless of whether you enter the password or not, it is also possible that there is a problem with the software itself, and you can monitor whether the software will fix itself later.

    If the answer is helpful, please click "Accept Answer" and kindly upvote it. If you have extra questions about this answer, please click "Comment".