Try the following strategies to troubleshoot problems with starting Classic and running Classic applications:
Ensure that a valid Mac OS 9 System Folder is listed and selected in Classic preferences.
If you encounter problems starting Classic, use standard Mac OS 9 troubleshooting techniques to diagnose and resolve the problem. For example, look in /System Folder/Preferences for damaged or corrupted system preferences, try discarding the MacTCP DNR file, or consider fonts or system extensions.
If Classic begins to start up but does not finish, it could be caused by a bad alias in the Servers folder in the Mac OS 9 System Folder. Try dragging the /System Folder/Servers folder to the Trash and restarting Classic.
Choose Turn Off Extensions in the Advanced pane of Classic preferences and click Restart Classic. If Classic is able to fully start up, troubleshoot for an extension conflict just as you would with a regular Mac OS 9 system.
If applications are crashing, check and increase their memory allocations, as needed.
Evaluate any third-party extensions or system enhancers for possible conflicts.
MORE INFO
Refer to Knowledge Base document 106677, "Troubleshooting the Classic environment in Mac OS X."