I suspect the problem will be if they have independent security tools near their network edge that MITM their own traffic, as discussed elsewhere on HN recently. If Microsoft are hard-coding addresses and certificate details for its online services within Windows itself, the security tools won&#x27;t be able to inspect that traffic, and will probably be set to block it by default.<p>I suspect the kinds of organisations operating these tools would consider that &quot;working as intended&quot; in most cases, but if it interferes with the enterprise-grade configuration and update management tools then that could be an issue for them.