how to delete files from iTunes without Time Machine deleting from external hard drive If I delete files from iTunes, does Time Machine automatically delete them when I plug in my external hard drive? And if so, how do I change this?
No - when you delete a file on your mac Time Machine explicitly keeps all copies of that file that have been backed up previously.



The only caution is now you have all those copies on one drive (presumably) and it is one mistake / error away from being lost. 

Also, if when your backup drive fills, Time Machine will start deleting from the oldest backup to make room for the estimated space needed for the current backup. Normally you won't lose all backups and all copies, but it is possible even if you have the "warn me after deleting backups" selected. In cases where new drives are added or there is an error / corruption to a file system causing a lot of data to get newly backed up, I have seen all but the most recent backup get deleted before you, the user is notified of the deletion.



You can prevent this one copy deletion by periodically cloning your backup volume or otherwise archiving a copy of your machine separately than the normal Time Machine process to ensure you always have more than one backup copy of a file that you have now deleted on your main iTunes library.