Notes from the field: some common dependencies for Microsoft 365 deployments

My blog posts take a while to get published these days. I struggle to find the time to write them and often a few notes can remain in draft form for a long time. Some of those notes never make it. Others possibly shouldn’t.

This is one of those posts where I’m not sure whether to publish or not. It’s based on an email I sent to a client, in 2018, as we were starting to work together. That client was about to embark on a migration to Windows 10 and Office 365, and these notes were intended to set them in the right path.

We all know that Office 365 is under constant development, and some of the advice below might not be current. I don’t think it’s too far off the mark but your mileage may vary. I’ve also added a few comments where I know we’d look to do things differently today. Those comments are marked with square parentheses.

All of these dependencies were things I identified before we got into design… but many more came out as we got into the detail.

Preparing the identity platform

[Identity is key to any successful Microsoft cloud implementation. And Azure AD is Microsoft’s cloud identity platform.]

Recommendation:

  • IdFix tool used to ensure that there are no directory issues that will cause synchronisation issues.
  • Azure AD Connect synchronising without error between on-premises Active Directory and Azure Active Directory. Even with on-premises authentication via ADFS or similar, user objects will be required in Azure AD in order to populate the Exchange GAL.

[in this case, I could be reasonably sure that both of these are already in place for the existing Skype for Business Online deployment.]

Useful links:

Preparing for Exchange hybrid

[It’s common to run Microsoft Exchange in a hybrid configuration when migrating mailboxes to Office 365. Generally, the hybrid will remain in place even after user mailboxes have been migrated to the cloud, for management purposes. There are constraints around the versions of Exchange Server that can be used though.]

  • The hybrid server must be running the latest or immediately previous (i.e. n or n-1) cumulative update or update rollup available for the version of Exchange installed on-premises
  • Domain names that will be used for email should have the appropriate records created and verified in DNS.
  • Ports should be enabled to allow traffic to flow as outlined in the above article. It may be useful to run the Remote Connectivity Analyzer (RCA) tools to verify this.
  • In addition, I recommend that the other Exchange servers in the organisation are upgraded to run with the latest available updates.

Useful links:

Preparation for deployment of Windows 10 images using SCCM

[System Center Config Manager (SCCM) is now part of Microsoft EndPoint Manager (MEM) and I’m not sure I’d recommend an SCCM-based deployment these days. My first preference would be to use Microsoft’s own Windows images, in Azure AD-joined configuration managed with Intune (also part of MEM). This topic would make a blog post on its own…]

Config Manager needs to be updated to align with the version of Windows 10 being deployed: Support for Windows 10 in Configuration Manager.

[Even when I wrote the notes 3 years ago, it seems I was guiding the client towards a Modern Device Management approach with Intune…]

Preparation for the use of Office applications (desktop and web)

[Office 365 ProPlus is now Microsoft 365 Apps for Enterprise but the advice below is unchanged apart from the product name.]

Office 365 ProPlus (i.e. subscription-based Office application) requirements are the same as for Office Professional Plus 2016 (i.e. perpetually-licensed applications) and are detailed at Microsoft 365 and Office Resources.

With regards to documents (including spreadsheets, presentations, etc.) containing macros, etc. It would be advisable to perform some basic compatibility testing: Check file compatibility with previous versions.

Office 2016 and 2019 are supported under the Fixed Lifecycle Policy.

Use of a supported browser is critical to the use of Office 365 web-based components although many organisations are held back by legacy software releases.

General Microsoft 365 system requirements may be found at the Microsoft 365 and Office Resources link above. Most notably:

“Microsoft 365 is designed to work with the latest browsers and versions of Office. If you use older browsers and versions of Office that are not in mainstream support:

  • Microsoft won’t deliberately prevent you from connecting to the service, but the quality of your Microsoft 365 experience will diminish over time.
  • Office 2019 connections to Microsoft 365 services will be supported until October 2023.
  • Microsoft won’t provide code fixes to resolve non-security related problems.

[Microsoft’s guidance previously stated that “Office 365 doesn’t support interoperability with any software that isn’t supported by its manufacturer.”]