Problem
In some versions of Windows, servers fail to navigate to the Microsoft site for either browsing or updates.
tl;dr
Start - Control Panel - Administrative Tools - Services
Disable the DNS Client service.
Solution
It turns out this is usually due to the DNS Client failing to properly cache the Microsoft site's DNS information.
DNS Client is a service that caches Domain Name System (DNS) names for the computer it's enabled on. If disabled, it simply means the system will go upstream to resolve DNS names rather than use the cache. Disabling this service usually results in the server being able to properly access the Microsoft site.
You can enable or disable this service by going to: Start - Control Panel - Administrative Tools - Services
- Updated