I messed this up once on my Mac, emptied Trash, felt sick for about ten seconds, then found out it was not always the end. The part that hurts people most is using the Mac like nothing happened. On an SSD, new writes chew through old space fast. When macOS reuses those blocks, recovery gets ugly.
I’d go through it like this.
1. Check Time Machine and iCloud first
This is the fast path. If your backups exist, you might be done in a few minutes.
- Open the folder where the file used to live, then enter Time Machine.
- Jump to a backup from before you emptied Trash.
- Restore the file.
- Then check iCloud.com and look at Recently Deleted for files, photos, or other synced stuff.
I’d start here before installing anything. Less risk, less mess.
2. Check for APFS snapshots
A lot of Mac users miss this one. macOS often keeps local APFS snapshots around, even when Time Machine was never fully set up. Open Disk Utility, pick your APFS Data volume, and see if snapshots exist from before the deletion. If one is there, your missing files might still be sitting inside it.
3. If backups fail, run recovery software
At this point I’d stop poking around and do a scan. Disk Drill is the one most people get running without much friction on newer Macs, including Apple Silicon models. The usual flow looks like this:
- Install the app.
- Select the drive where the deleted files were stored.
- Run the scan.
- Preview what it finds.
- Recover files to a different drive if you have one.
If you want a free route, PhotoRec exists. I used it once. It works, sort of, but the output was messy. Filenames were gone, folders were gone, and sorting through the results took forever.
One more thing, SSDs on Macs use TRIM. This matters. TRIM clears deleted data much faster than old spinning drives did, so time matters more than people think. If you keep installing apps, downloading stuff, or moving files around, your odds drop.
So my order would be simple. Check Time Machine. Check iCloud. Look for APFS snapshots. If none of those save you, run a recovery scan right away. I’ve seen files come back after Trash was emptied, mostly when the person stopped using the Mac immediatly and started recovery early.


Since these are work files, contact your IT team before installing recovery software. Many companies keep hidden endpoint backups, Microsoft 365 retention copies, SharePoint recycle bins, or server archives.
Give IT the exact filename, original folder, aprox deletion date, and your Mac serial number. Ask them to restore a copy into a new folder, without overwriting anything.
This route is simpler and safer. It avoids extra SSD writes and messy scans. Act fast. Company retention periods often expire after 30 to 90 days, and IT might recieve your request faster with precise file details.
The download itself is the trap nobody flags. If you install a recovery tool onto the same drive that holds your deleted files, you’re writing new data right where the old data sits. On an internal Apple Silicon disk that can quietly overwrite the exact blocks you’re chasing. Grab the installer on a different machine or drop it on a USB stick and run it from there if you can. Sounds picky, but it’s the kind of mistake that turns a recoverable file into a dead one.
On Disk Drill, I’d frame it a bit differently than the earlier posts. The preview and the clean interface are nice and all, but the thing worth knowing on Mac is the paywall sits after the scan. The free version happily scans and shows you what it thinks it found, then asks for money before it actually restores anything. That’s not a scam, it just means you can confirm your files are recoverable for zero dollars before deciding to pay, which is honestly a decent way to test your odds before spending. Just don’t assume the free scan equals free recovery.
For work docs specifically, I’m with the crowd that says software should be your last stop, not your first. @darkhacker41 is right that IT often has retention copies you don’t even know exist, and that route creates zero writes on your Mac. If your job uses Microsoft 365 or Google Workspace, the deleted-items and version history there will out-recover any disk scan nine times out of ten. Exhaust the boring copies first, then reach for the scanner.