SQL Server Database Not Shrinking I have an SQL Database with a lot of unused space.
However when I run 
Tasks | Shrink | Database 
And
Tasks | Shrink | Files
from Management studio it isn't freeing up any space.
Unfortunately the machine that it is running on is running out of hard disk space. Any ideas on why this space isn't freeing up.

Also recovery mode on DB is set to simple.


Here is the unused dialog that comes up when I go to shrink files:


I've also tried doing this via T-SQL


  DBCC SHRINKDATABASE (myDatabase, 5);


I get following response:

DBCC SHRINKDATABASE: File ID 1 of database ID 6 was skipped because the file does not have enough free space to reclaim.
DBCC SHRINKDATABASE: File ID 2 of database ID 6 was skipped because the file does not have enough free space to reclaim.
DBCC execution completed. If DBCC printed error messages, contact your system administrator.
I'm going to make a wild guess and say that your database is set up to use FULL recovery.  You have never taken a log back up (let alone a full one) based on the image above.  If this is the case then you log file is growing and growing and can't clear out because you haven't taken a backup.  

If you have the room take a full backup, then a log backup and try your shrink again.  Should work fine. 

Worst case (and I do mean worst, particularly if this is a production database) is to set the database to SIMPLE recovery, shrink and then take a backup.  This should work even though you don't have enough space for a shrink normally.

At this point make sure you set up regular backups for your database.

You can go here for more detail.



EDIT: 

Can you tell us what % free the log is vs the data file?
Also you might look at the log_reuse_wait_desc in sys.databases.

SELECT name, log_reuse_wait_desc FROM sys.databases 


And last but certainly not least have you tried the TRUNCATEONLY option of shrink?

DBCC SHRINKFILE (Adventureworks2008R2_Log, TRUNCATEONLY)