Routing (chaining) failure

Question

Hi Folks!
I'm seeing a Routing (chaining) failure
every time the localhost tries to download CRL updates from the Internet.
I checked the System Policy and it has an enabled rule from localhost to All Networks for CRL updates.
This is the first entry in the connection;
Failed Connection Attempt
EDGE 3/7/2014 6:04:12 PM
Log type:
Web Proxy (Forward)
Status: 12206 Forefront TMG detected a proxy chain loop. There is a problem with the configuration of the Forefront TMG routing policy. Please contact your server administrator.
Source:
Local Host (WAN IP:10475)
Destination:
External (a23-59-190-136.deploy.static.akamaitechnologies.com 23.59.190.136:80)
Request:
HEAD http://23.59.190.136/v10/1/microsoftupdate/redir/muredir.cab?1403080204
Filter information:
Req ID: 0b21a351; Compression: client=No, server=No, compress rate=0% decompress rate=0%
Protocol:
http
User:
anonymous
Additional
information
Client agent: Windows-Update-Agent
Object source: (No source information is available.)
Cache info: 0x10 (Request includes the VIA header.)
Processing time: 1 MIME type: -
This is the second error and it shows a 500 Internal Server Error (which may be significant);
Allowed Connection
EDGE 3/7/2014 6:04:12 PM
Log type:
Web Proxy (Forward)
Status:
500 Internal Server Error
Rule:
[System] Allow all HTTP traffic from Forefront TMG to all networks (for CRL downloads)
Source:
Local Host (WAN IP:10432)
Destination:
External (a23-59-190-136.deploy.static.akamaitechnologies.com 23.59.190.136:80)
Request:
HEAD http://23.59.190.136/v10/1/microsoftupdate/redir/muredir.cab?1403080204
Filter information: Req ID: 0b21a34b; Compression: client=No, server=No, compress rate=0% decompress rate=0%
Protocol:
http
User:
anonymous
Additional
information
Client agent: Windows-Update-Agent
Object source: Internet (Source is the Internet. Object was added to the cache.)
Cache info: 0x48040010 (Request includes the VIA header. Response includes the CACHE-CONTROL: NO-CACHE or PRAGMA: NO-CACHE header. Response includes the VIA header. Response should not be cached.)
Processing time: 1 MIME type:
text/html
These errors only occur when the Localhost tries to download CRL Updates from the Internet. The system policy rule that allows this behavior is enabled.
Can anyone help with addressing this issue other then posting up a link to some article that has nothing to do with this issue? :)
Q: Marking a question as answered when it's not - is this something new? A: Not at all, it's standard Nick Gu!

Answer 1

DNS is fine. As you can see from the logs name resolution (reverse lookups) is fine;
External (a23-59-190-136.deploy.static.akamaitechnologies.com 23.59.190.136:80)
So the localhost has been able to resolve the IP address with no problems.
I'm starting to think this is a bug/flaw with TMG 2010. This happens with every install I've ever done.
Q: Marking a question as answered when it's not - is this something new? A: Not at all, it's standard Nick Gu!