I can update via roster's update page without issue. However, when we try to update via UU we get:

[2008/05/05 17:16:44] Uploading to Primary URL...: http://roster.astralorder.com/index.php?p=update
[2008/05/05 17:16:44] PvPLog.lua - 90% Compressed. Upload Size: 6.50 KB
[2008/05/05 17:16:44] CharacterProfiler.lua - 87% Compressed. Upload Size: 61.19 KB
[2008/05/05 17:16:56] Upload Error: The underlying connection was closed: An unexpected error occurred on a receive.

This is using the password field to process all available levels of update:
Admin
Officer
Guild
Public

I have the Character uploads allowing public, the guild updates at officer+. All addons are public updates (just to see if this is the issue, it's not), and "Enforce Upload Rules" is set to never to rule that one out as well.

Thoughts?

Upload Error: The underlying connection was closed: An unexpected error occurred on a receive.

This is a connection error, probably nothing to do with Roster itself

I wonder if Matt has any insight on this

I'm not getting anything on my server's error log, is there anyway to see what this "error" is that UU is blabbing about?

Look at the debug tab

Hehe, that's where I got the info I supplied in the OP

zanix wrote:

Upload Error: The underlying connection was closed: An unexpected error occurred on a receive.

This is a connection error, probably nothing to do with Roster itself

I wonder if Matt has any insight on this

I actually had the same problem and fixed it by clicking on clear SV's.
Don't know why but it worked, thinking it got corrupted somehow..