Users can Edit over Web but not iCal

My iCal server was running fine for months. My Groups had calendars enabled and the members of that group saw those calendars in iCal under Accounts->Delegation. I don't know when this happened but now when I add new members to the group, they can't see the group name in their iCal Delegation. They can edit the calendar via the web, but iCal can't see it at all. The users who had delegation set up properly for their group calendars have not been affected for those old calendars, but when I that user to another calendar-enabled group, that calendar does not show up in the delegation list.
I can see this work by viewing the settings in Safari.
I have a user named 'stupid' and a group named 'test'.
'Stupid' has calendaring enabled. 'Test' has wiki, blog, and calendaring enabled. Group members only are able to read and write to these services. 'Stupid' is the only member of the group 'test', and that is 'stupid's only group.
When I go to look at the principles in Safari (http://server:8008/principals/_uids_/35E60BF4-2915-482A-805F-CC72AF5058FF/)
I get this:
Directory Information
Directory GUID: 058167af-ace8-519a-ac3d-e166498db024
Realm: /Search
Principal Information
GUID: 35E60BF4-2915-482A-805F-CC72AF5058FF
Record type: groups
Short name: test
Full name: test
Principal UID: 35E60BF4-2915-482A-805F-CC72AF5058FF
Principal URL: /principals/_uids_/35E60BF4-2915-482A-805F-CC72AF5058FF/
Alternate URIs:
-> /principals/groups/test/
Group members:
-> (users) stupid
Group memberships:
Calendar homes:
-> /calendars/_uids_/35E60BF4-2915-482A-805F-CC72AF5058FF
Calendar user addresses:
-> https://classics.uc.edu:8443/principals/groups/test/
-> https://classics.uc.edu:8443/principals/_uids_/35E60BF4-2915-482A-805F-CC72AF5058FF/
-> /principals/_uids_/35E60BF4-2915-482A-805F-CC72AF5058FF/
-> http://classics.uc.edu:8008/principals/_uids_/35E60BF4-2915-482A-805F-CC72AF5058FF/
-> http://classics.uc.edu:8008/principals/groups/test/
-> urn:uuid:35E60BF4-2915-482A-805F-CC72AF5058FF
-> /principals/groups/test/
So the iCal server sees 'stupid' as a member. But when I look at the proxy-write (http://server:8008/principals/_uids_/35E60BF4-2915-482A-805F-CC72AF5058FF/calendar-proxy-write/) I get:
Directory Information
Directory GUID: 058167af-ace8-519a-ac3d-e166498db024
Realm: /Search
Parent Principal Information
GUID: 35E60BF4-2915-482A-805F-CC72AF5058FF
Record type: groups
Short name: test
Full name: test
Principal UID: 35E60BF4-2915-482A-805F-CC72AF5058FF
Principal URL: /principals/_uids_/35E60BF4-2915-482A-805F-CC72AF5058FF/
Proxy Principal Information
Principal UID: 35E60BF4-2915-482A-805F-CC72AF5058FF#calendar-proxy-write
Principal URL: /principals/_uids_/35E60BF4-2915-482A-805F-CC72AF5058FF/calendar-proxy-write/
Alternate URIs:
-> /principals/groups/test/calendar-proxy-write/
Group members (Editable):
Group memberships:
Same thing in proxy-read. So while the iCal server does see 'stupid' as a member of 'test', it isn't really.
Something similar shows up for older groups. When I click on proxy-write for an older group I can see all of the members that were there months ago, but newly added members (that is users that have been on the server for at least a year but are new to the group) don't show up in the list.
When I go to iCal and add 'stupid' as an account I can see and edit 'stupid's calendar, but nothing shows up under delegation.
Service Access allows all users and groups to the iCal service.
I have stopped and restarted the iCal service and the server itself several times. I have also checked for users in both OD and Local. All users are OD only.
The only thing I can get from my iCal error log is:
2008-08-26 22:21:32-0400 [-] [caldav-8009] [AMP,client] Unauthenticated users not enabled with the 'calendar' SACL
2008-08-26 22:21:32-0400 [-] [caldav-8009] [AMP,client] Allow proxy: user 'wikiserver' as 'test'
2008-08-26 22:21:32-0400 [-] [caldav-8009] [AMP,client] REPORT /calendars/groups/test/calendar/ HTTP/1.1
2008-08-26 22:22:02-0400 [-] [caldav-8009] [AMP,client] Unauthenticated users not enabled with the 'calendar' SACL
2008-08-26 22:22:02-0400 [-] [caldav-8009] [AMP,client] Allow proxy: user 'wikiserver' as 'test'
2008-08-26 22:22:02-0400 [-] [caldav-8009] [AMP,client] REPORT /calendars/groups/test/calendar/ HTTP/1.1
2008-08-26 22:22:15-0400 [-] [caldav-8009] [AMP,client] PROPFIND /calendars/_uids_/7FD3BB44-70E4-4AE1-9AA0-A83D278F8544/ HTTP/1.1
2008-08-26 22:22:15-0400 [-] [caldav-8009] [AMP,client] PROPFIND /calendars/_uids_/7FD3BB44-70E4-4AE1-9AA0-A83D278F8544/inbox/ HTTP/1.1
2008-08-26 22:22:33-0400 [-] [caldav-8009] [AMP,client] Unauthenticated users not enabled with the 'calendar' SACL
2008-08-26 22:22:33-0400 [-] [caldav-8009] [AMP,client] Allow proxy: user 'wikiserver' as 'test'
2008-08-26 22:22:33-0400 [-] [caldav-8009] [AMP,client] REPORT /calendars/groups/test/calendar/ HTTP/1.1
and this is the last bit of my access log:
10.138.1.222 - stupid [26/Aug/2008:22:23:40 -0400] "PROPFIND /principals/_uids_/C6CF9F8A-3532-4D81-A4B7-823FC0262AA8/ HTTP/1.1" 207 1188 "-" "DAVKit/2.0 (10.5.4; wrbt) iCal 3.0.4" [16.9 ms]
10.138.1.222 - stupid [26/Aug/2008:22:23:40 -0400] "PROPFIND /principals/_uids_/C6CF9F8A-3532-4D81-A4B7-823FC0262AA8/ HTTP/1.1" 207 432 "-" "DAVKit/2.0 (10.5.4; wrbt) iCal 3.0.4" [11.5 ms]
10.138.1.222 - stupid [26/Aug/2008:22:23:40 -0400] "PROPFIND /principals/_uids_/35E60BF4-2915-482A-805F-CC72AF5058FF/ HTTP/1.1" 207 321 "-" "DAVKit/2.0 (10.5.4; wrbt) iCal 3.0.4" [8.8 ms]
10.138.1.222 - stupid [26/Aug/2008:22:23:40 -0400] "PROPFIND /principals/_uids_/C6CF9F8A-3532-4D81-A4B7-823FC0262AA8/ HTTP/1.1" 207 1188 "-" "DAVKit/2.0 (10.5.4; wrbt) iCal 3.0.4" [10.6 ms]
10.138.1.222 - stupid [26/Aug/2008:22:23:40 -0400] "PROPFIND /principals/_uids_/C6CF9F8A-3532-4D81-A4B7-823FC0262AA8/ HTTP/1.1" 207 432 "-" "DAVKit/2.0 (10.5.4; wrbt) iCal 3.0.4" [8.9 ms]
10.138.1.222 - stupid [26/Aug/2008:22:23:40 -0400] "PROPFIND /principals/_uids_/35E60BF4-2915-482A-805F-CC72AF5058FF/ HTTP/1.1" 207 321 "-" "DAVKit/2.0 (10.5.4; wrbt) iCal 3.0.4" [8.6 ms]
10.138.1.254 - - [26/Aug/2008:22:24:03 -0400] "REPORT /calendars/groups/test/calendar/ HTTP/1.1" 401 141 "-" "-" [3.7 ms]
10.138.1.254 - "(sudoers)wikiserver as (groups)test" [26/Aug/2008:22:24:03 -0400] "REPORT /calendars/groups/test/calendar/ HTTP/1.1" 207 4361 "-" "-" [107.0 ms]
10.138.1.254 - - [26/Aug/2008:22:24:34 -0400] "REPORT /calendars/groups/test/calendar/ HTTP/1.1" 401 141 "-" "-" [4.1 ms]
10.138.1.254 - "(sudoers)wikiserver as (groups)test" [26/Aug/2008:22:24:34 -0400] "REPORT /calendars/groups/test/calendar/ HTTP/1.1" 207 4361 "-" "-" [118.1 ms]
10.138.1.254 - - [26/Aug/2008:22:25:04 -0400] "REPORT /calendars/groups/test/calendar/ HTTP/1.1" 401 141 "-" "-" [4.5 ms]
10.138.1.254 - "(sudoers)wikiserver as (groups)test" [26/Aug/2008:22:25:04 -0400] "REPORT /calendars/groups/test/calendar/ HTTP/1.1" 207 4361 "-" "-" [123.6 ms]
10.138.1.254 - - [26/Aug/2008:22:25:34 -0400] "REPORT /calendars/groups/test/calendar/ HTTP/1.1" 401 141 "-" "-" [4.0 ms]
10.138.1.254 - "(sudoers)wikiserver as (groups)test" [26/Aug/2008:22:25:34 -0400] "REPORT /calendars/groups/test/calendar/ HTTP/1.1" 207 4361 "-" "-" [115.2 ms]
So if Workgroup Manager doesn't edit the iCal sql tables properly, what else can I use?

Making a user a member of a group does not automatically make them a delegate of that group. They are members in the sense that they have full read-write access to the group data, but they won't have that group show up as a delegate.
To make a user a delegate of a group, someone who is a member of that group needs to create a new account in iCal and set the server account URL to point to the groups principal path (/principals/groups/testgroup/ as the path in the URL) then they should add the user as a delegate via the iCal preferences panel for that account.

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