Trying to do this as painless as possible. Screwed it up once and lost my whole library. I was able to recover it from time machine from earlier in the day. Let me give you my scenario and tell me what the best way of doing this is. 2015 iMac with internal 480 GB SSD External 1 TB spinner in a 2 port bay All physical mp3 files are stored on my SSD on the desktop in a folder called "Music Files". These are all organized how I want, single mp3's in one folder, all albums in their own folders. Total files = 13,952 songs as per iTunes, 99.77 GB) All physical video/movie files are stored on the external drive in a folder called "Movies". Total files = 144 movies, 157.74 GB I now want to possibly move the physical location of the MP3 files over to the external in order to save space on the SSD. I tried copying my iTunes Library folder and pasting it on the external and copy/pasting the whole MP3 folder to the external as well. I changed the media location in iTunes to the new folder and reopened iTunes while holding the shift key and tried pointing it to the new library location. I know this may be obvious that it won't work that easy. How can i achieve this without screwing up my physical library and its organization but get iTunes to read the physical file in its new location but use the same library/setup/playlists? Can i just copy the folder over, delete the music folder on the SSD and when iTunes tries to "locate" the file, just point it to the new folder on the external (using the same folder structure the old folder did). I want to keep the iTunes library exactly as it is, playlists and all, just need the physical location of the mp3 files to be on the external and not the SSD. is that easier than transferring a whole library or is that not how it works.