I tried to save a webpage in Safari as a PDF by hitting Command-P, then “Save as PDF”. I attempted to save this to an external hard drive. Upon closing Safari and clearing my search history in Safari, I realized the document that I thought I saved as a PDF was not on the external hard drive.

Any chance of retrieving this document which I thought I saved? Was it ever even saved at all?

Upon trying to replicate my actions to see where I may have gone wrong, I noticed an error message flash across the screen after I hit save reading “error while printing”.

I’m running Safari 10.1 (12603.1.30.0.34) on a MacBook Pro with macOS Sierra version 10.12.4. I did have Time Machine running. Document lost was the private key to a Bitcoin paper wallet.