I'm new to TMG, and have just setup a new TMG server. I can't get the updates to work. I thought it was the firewall blocking the requests, but I tried making a very open firewall rule and also shut off the Microsoft Forefront TMG Firewall service. Shutting off the firewall seemed to disable the checks. I've also set the proxy using, "netsh winhttp set proxy", using the netbios and FQDN of the proxy. Any help would be appreciated.
Here's one of the events that may have something to do with it:
Failed Connection Attempt
Log type: Web Proxy (Forward)
Status: 10060 A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond.
Rule: [System] Allow HTTP/HTTPS requests from Forefront TMG to specified sites
Source: Local Host (127.0.0.1:25309)
Destination: External (22.214.171.124:443)
Filter information: Req ID: 100caf94; Compression: client=No, server=No, compress rate=0% decompress rate=0%
Object source: Internet (Source is the Internet. Object was added to the cache.)
Cache info: 0x0
Processing time: 0 MIME type: