In an interesting twist of additional information, I just tried running wyUpdate with the exact same app (same version of wyUpdate and server service) on a different server, all within the same local domain and it updates fine. I then returned to the first server and am getting the same error. I copied the working wyUpdate from the second server to the first server and it failed, despite working fine on the second server.
The first (failing) server does have internet access, I confirmed by loading the url in the error message in a browser.