My Favorite Tools to Use with Office 365

The Office 365 Tools and Diagnostics site provides a comprehensive list of tools to diagnose and troubleshoot O365 services across all plans/subscriptions.

Prior to migrating mailboxes to O365, I use MessageOps Office 365 Client Updater to ensure machines with Windows 7 and older, and Office 2010 and older have the prerequisite software and updates installed for compatibility with O365 resources. I deploy the updates via group policy (GPO).

For older Office 365 implementations using older versions of DirSync (that do not include password sync), I have used MessageOps Office 365 Password Synchronization Tool to sync passwords to O365. It works the same way that the newer versions of DirSync with Password Sync do.

If you need to import PST files into Office 365, don’t bother with the Microsoft’s PST Capture tool. Instead, use MessageOps Office 365 Exchange Migration Tool. Though the tool requires licensing, it is far superior in reliability and migration speed than PST Capture.

The IdFix DirSync Error Remediation Tool helps with identifying on premise user accounts that likely will not sync to Office 365 for easy and quick remediation.

Microsoft’s Remote Connectivity Analyzer (aka ExRCA) is the Swiss Army knife (if you will) to test and troubleshoot connectivity issues with Exchange, Office 365, and Lync as well as analyzing message headers.

To test free/busy in an Exchange Hybrid environment, I will use the Hybrid Environment Free/Busy Troubleshooter.

In planning for an Exchange hybrid configuration, we can request a free product key at the Exchange Hybrid Product Key Distribution site. The hybrid key can be used to incorporate an Exchange 2010, 2013, or 2016 server into our environment. However, the license agreement states mailbox cannot be hosted on a server with a hybrid product key–hence the reason for the key being free. In my experience with Exchange 2013, I have seen in some cases where the mailbox cmdlets are not available. The hybrid configuration acts as the bridge for migrating mailboxes from legacy versions of Exchange (2003, 2007 or 2010) to Office 365 to provide a seamless experience for the end user. NOTE: Access to the hybrid key distribution site requires IE9 or newer, Windows 7 or newer, and .NET Framework 3.5.

These 3 sites are a veritable “one stop shop” of useful links to O365 resources…

7 thoughts on “My Favorite Tools to Use with Office 365

      • I’m not using Dirsync i’m using “MessageOps Office 365 Password Synchronization Tool” version is the version listed when I right click the executable. Planning on upgrading to AAD Sync tool. I appreciate the reply Thank You.

      • Just so I am clear, you are not using DirSync currently to synchronize users to O365? If not, what are you synchronizing passwords to? Were your accounts in O365 created manually in the portal?

      • Yes accounts are created manually… I’m trying to deliver these guys from the stone ages lol. No, they are not using DirSync.

      • NOTE: This is not a trivial task. I provide no guarantees in the tasks outlined and strongly recommend you contact O365 support for assistance before performing any work regarding your specific requirements.

        Because the users were created manually and now AADSync is to be implemented, care must be taken as to not break the existing users in O365 when syncing from on premise. Doing so could cause loss of data.

        Because users exist (un-synched) in O365, one must prepare the on premise objects for “soft matching” to the users in O365. Review TechNet and other articles for “soft matching” or SMTP matching to O365 (i.e.

        Before you start, however, does the O365 subscription you have allow for directory synchronization? If so, review the following and test in a lab environment before implementing in production. If not, AADSync will not work.

        1) Add UPN suffixes in AD for the domain(s) that is hosted in O365
        2) Update user logon names with the UPN suffix in AD to match the primary email address set for the associated users in O365
        3) Run IDFix (MS tool) to ensure the on premise accounts are configured and set properly
        4) Enable AD Synchronization in O365
        5) Download the latest version of AADSync (
        6) Prepare a Windows 2012 R2 (recommended) domain-joined server for AADSync (
        7) Install AADSync ( but do not sync yet
        8) Remove all traces of MessageOps O365 Password Sync
        9) Configure AADSync for filtering
        10) Run sync for AADSync

        Again, I offer no guarantees and cannot be held liable. Performing these tasks are at your own risk.

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