To try to get Office 2016 and 2019 users to move to a more recent version of Office – like Office LTSC or Office 2021 – from versions of Office that have exited mainstream support, Microsoft basically is playing a game of chicken with customers. Continuing to use Office 2016 and 2019 might be risky because some features may encounter “unexpected issues.” (Or, you know, they may not….) Because of this possibility, Microsoft’s official statement is these non-subscription Office clients won’t be “supported” by Microsoft after that date, even though users won’t be stopped from connecting to those services. (Generating uncertainty around “support” isn’t a Microsoft tactic that’s unique to Office. Other examples: Users can run Windows on Apple silicon but they won’t be “supported” if they do this. Another: Users can run Windows 11 on PCs that don’t meet the TPM and CPU requirements, but they won’t be “supported” by Microsoft if anything goes awry.) Back to Office. I asked for clarification of this July 25 Microsoft TechCommunity article, which says “Office 2016 & 2019 won’t be supported for connecting to Microsoft 365 services, including Exchange Online, starting Oct 2023 …. Don’t wait until the last minute - now is a great time to upgrade.”  A Microsoft spokesperson sent the following statement: “Microsoft will NOT be blocking supported and up-to-date Office clients from connecting to M365 cloud services. However, as announced in April 2017 and clarified in February 2018, Microsoft plans to stop supporting Office clients out of mainstream support when connecting to Microsoft 365 cloud services. “Practically, this means that as we make updates to Exchange Online, SharePoint Online, and other Microsoft 365 services, we will not be building around the constraints inherent in the older perpetual Office clients that are already out of mainstream support. Customers will not be blocked in connecting, but they may not get the full value out of new investments in our cloud services. Over time, they may run into unexpected issues.” In short: Office 2016 and 2019 will continue to work with Microsoft 365/Office 365 back-end services at least until those Office editions are out of support, which means October 2025. They just might (or might not) work well, especially starting next year, so it’s a “use at your own risk” situation.