I've recently updated our client machines from 10.3 to 10.7 in hopes that it would solve the "Could not contact server" error that many of our users are now seeing when trying to update; however, some of the clients (all on a SBS 2008 domain) update just fine, some intermittently, and some not at all. This just started happening 2 weeks ago on July 10. Here's an example of one that intermittently works:
And one that doesn't:
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