As I still use Mac OS 8.6, I can't say whether your problem relates to using PlusOptimizer with OS X. However, I got exactly the same error message when trying to optimize my hard drive with PlusOptimizer (which had always worked without problems before) AFTER I had first tried to optimize with TechTool Pro 3.4. Techtool stopped the optimization process because a file (System File) was too large for the largest available bit of contiiguous free space. TechTool requires that file defragmentation is completed before free space is defragmented. But it cannot defragment a file unless there is a sufficiently large amount of contiguous free space in which to transfer the file. When I tried to run PlusOptimizer after getting this message from TechTool, Plusoptimizer stopped, before starting to do anything, with the same message you received.