You'll never get all of the sensitive data off of it by deleting it piecemeal. There's just too much private data generated from normal usage. You can get an i

You'll never get all of the sensitive data off of it by deleting it piecemeal. There's just too much private data generated from normal usage. You can get an impression of how much by searching for "forensic artifacts." Here's a taste: https://docs.google.com/spreadsheets/d/1X2Hu0NE2ptdRj023OVWIGp5dqZOw-CfxHLOW_GNGpX8/edit#gid=1317205466 https://docs.google.com/spreadsheets/d/1X2Hu0NE2ptdRj023OVWI... That's not even a complete list. For example, I think it's missing the QuickLook cache that contains thumbnails of all the things you've previewed recently. So the checklist is simple: 1. Backup your drive. 2. If FileVault wasn't turned on, turn it on and wait for it to finish encrypting the disk. 3. Erase the disk and reinstall the operating system. EDIT: Forgot that not everyone has FileVault turned on. Turn on FileVault, everyone!