Is It a Best/Recommended Practice to Update a Server Application when Clients/Apps May Not Be Compatible with the Version?

Problem scenario
Some updates are essential for security. In some situations a patch to an OS or an application may cause some clients to have problems connecting to the server. The ramifications could apply to middleware or other applications. Is it a best/recommended practice to push an update to a server's OS or application when other clients or smart phone apps will not be able to be compatible?

It is not clear. Here is one example where "best practices" are not compatible:

TechRepublic says it is a best practice to tolerate system incompatibilities (#8 here). On the other hand, a well-respected website, that gives advice to programmers, recommends eliminating incompatible versions by forcing updates.

From a pragmatic perspective in an enterprise environment, managers wrestle with problems like this. There may not be two options that are clear cut. Forbes uses phrases like "the right security controls" as a best practice. It is a safe bet to use the Goldilicks approach as a "best practice." With qualifiers and specific context, "best practices" can have applicability.

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