Hi Jack this is the relevant FAQ page for index in error state: 
http://code.google.com/appengine/kb/general.html#error_indexes

Please follow this steps to vacumm and rebuild your indexes: 

   1. Create a backup of your index.yaml specification
   2. Determine the indexes in state ERROR from the admin console
   3. Remove the definitions of the indexes in ERROR from your index.yaml 
   file.
   4. Run appcfg.py vacumm_indexes app_dir/
   5. Wait until the ERROR indexes no longer appear in the admin console.
   6. Replace the modified version of your index.yaml file with the 
   original.
   7. Run appcfg.py update_indexes app_dir/

Documentation:

   - vacuum_indexes
   - Python Docs: 
      
http://code.google.com/appengine/docs/python/tools/uploadinganapp.html#Deleting_Unused_Indexes
      - Java Docs: 
      
http://code.google.com/appengine/docs/java/tools/uploadinganapp.html#Deleting_Unused_Indexes
   - update_indexes
      - Python Docs: 
      
http://code.google.com/appengine/docs/python/tools/uploadinganapp.html#Updating_Indexes
      - Java Docs: 
      
http://code.google.com/appengine/docs/java/tools/uploadinganapp.html#Updating_Indexes
   
If the problem persists, check if you are not creating a case of exploding 
indexes:
http://code.google.com/appengine/docs/python/datastore/queries.html#Big_Entities_and_Exploding_Indexes

Hope This Helps!
Jose

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