I'm unable to empty my trash folder

Question

The HD on my macBook pro ( 10.7.5, 8Gb RAM) has 254 files in the trash ( the 500gb HD is full) When I try to empty the trash I'm asked if I want to "secure empty trash" which I confirm, then I select : remove all items" but after pausing for a few seconds, the dialogue box goes and nothing has happened- I still have 254 files ( NOT locked) in mt trash taking up I guess some 50-100gb of space) that i can't empty.
I have run disk utility and repaired my disk - and restarted, and I still can't empty the trash.. and ideas?

Answer 1

You could try starting up in SafeBoot, note the items in trash then,
while in SafeBoot, run Disk Utility's 'repair disk permissions' and
then restart the computer. This may help some underlying issues
that could contribute to your user account and it's trash situation.
There may be some sticky permissions issue(s) behind hard to
remove trash items... so that is why it sometimes is necessary
to try a different method to make it happen.
•You can't empty the Trash or move a file to the Trash - Apple Support
This covers most aspects of trash problems, so it's worth reading.
There are other ways, for each user account to accumulate trash
and methods to remove them include command-line as well as
third party tools (such as OnyX) which allows an admin user to
deploy a trash empty device from within the tool set.
Good luck & happy computing!