Find the jakarta iis module logs to diagnose the problem. If the logs are not created, the problem is getting the module to load/run or its a misconfiguration.
If the logs are created, enable debugging level output in the jakarta module setting to help you diagnose the problem.
Check that the Jakarta filter module has a green upwards pointing arrow, not a red one. If it is red, check the application event log. If nothing is in the log, send a request to the web service that should be forwarded to tomcat (i.e. the (sub)domain of the website running in tomcat)
The application Event log in windows can give you useful hints. A good collection of possible causes are here: http://blogs.msdn.com/david.wang/archive/2005/06/21/HOWTO_Diagnose_and_Fix_Common_ISAPI_Filter_Installation_Failures.aspx
The 'data' part of the message (for example 02 00 00 00) is an error code, which can come from windows OR the dll. In case it comes from windows you can use: "NET HELPMSG 2" to get the message in clear text.
If you get the 02 (file not found) or 05 (Access denied) you can try to use Sysinternal's FileMon utility to figure out exactly which file it is failing to load. It could be the dll, or one of its config files (or possible something completely different :-).
In some setup instructions it says that you can put the jakarta settings in the registry. This did not work for me!
I had to put them in a file instead!
If registry settings are not working and you are sure you spelled the keys correctly and put them int the correct place - and they are readable by the IIS users - try using a config file instead.
Of course - make sure your config files are correct. The Jakarta logs will help you with this.