Q: problem with deleting files OSX Mavericks 10.9.5

Did you try restarting, or shut down and restart anew?

You may have to start in safe mode, and repair disk permissions

with disk utility, to see if that helps any system files that may be

damaged. Or consider using OS X Utilities in Recovery to check

and maybe repair the hard drive.

There are several things that may need to be done. If it were

mine, I'd probably be super careful in deleting files if any chance

of removing system-owned files were to occur, as trouble results

if or when that happens. The restart may put the trash items fully

in the trash. You could also look into the health of the hard drive

to see if that may be too full or otherwise failing. In an older Mac

or any computer, a hard disk drive may wear out unexpectedly.

And an SSD may have irregularity and need some meds.

• Try safe mode if your Mac doesn't finish starting up - Apple Support

Also there likely is some method of starting up in single-user mode

or terminal and using a unix command to empty trash(es) as there

are more than one in the OS X. An admin sees one, generally.

• Mac OS X: How to start up in single-user or verbose mode - Apple Support

• About the screens you see when your Mac starts up - Apple Support

Some users have acquired OnyX utility for their version of OS X, and

carefully use some of its tools, to empty trash and perform other duties

as this can go into the lower level behind the graphic user interface. It

also can cause problems. You may be able to use OS X Utilities as part

of OS X Recovery, and straighten out some issues that way, with disk

utility. Usually an occasional simple restart can help with trash issues.

And once in awhile you may have to unlock ownership or change

permissions and the like, to get a file so it will go away. Be aware

that some files belong to the system, and should not be trashed.

In any event...

Good luck & happy computing!

Yes, the 'Secure Empty Trash' feature will take more time because it likely will

secure over-write the content instead of just tagging it for eventual overwrite...

Since I don't create or handle documents considered secure, or files that may

need encryption, seldom has this feature been exercised by me. However on

another hand, I've securely erased hard drives between full re-installations;

especially if the machine is going to a new home, donated, traded, or sold.

Good to hear you resolved the issue and your Mac is fine!