Can't Delete Some Files From Trash?

You can't empty the Trash or move a file to the Trash and Solving Trash Problems

 

Before, I thought you had to logout, but before doing that, you can try emptying trash while pressing option or shift-option. That's from support.apple.com/kb/HT1526 and it worked for me.

 

On another Thread about deleting garbage somebody talked about a FreeWare App called Trash It! I downloaded it and it is working far better than I had hoped it would.

On Friday night I started deleting Archive files on an external drive. These files date back to the start of the year and are obsolete. For the most part they were deleted on the scale of 4K, 8K and occasionally on 12K scale. There were, maybe, 6GB total deleted. In about the time it took to eat Sunday Dinner OVER 30GB have been deleted. I'm finally seeing files deleted in Wholesale rather than Retail size.

Trash It!

 

In most cases, app removal software such as TrashIt! doesn't do a thorough job of finding and removing files/folders related to deleted apps. For more information, read this and this. If you just want to delete the app, drag the .app file to the trash. No other software needed. If you want to completely remove all associated files/folders, no removal apps will do the job.

The most effective method for complete app removal is manual deletion:

Best way to FULLY DELETE a program​