Two days of file edits inexplicably disappeared

Question

I have a 2021 MacBook Pro and I use the Dropbox app to automatically upload every document I work on to Dropbox. Two days ago, I updated my OS to Tahoe 26.4.1. The update seemed to work fine, and I continued working on a Word document I had been editing for the next two days. I always save after every line I write, and while I didn't check the Dropbox app to confirm that my edits were being uploaded, I had no reason to suspect it wasn't (when I look at my "Recent" files on the Dropbox website, I see that a number of files were uploaded between now and then). But then, just now, I opened up the Word document to discover that all my edits (as well as the "last saved" time) had reset to what they were two days ago, before the OS update. This is the case both in Finder and when I go to the Dropbox website. The "Rewind" feature does not show any activity in the folder in which the document was stored over the last two days, despite the fact that I probably saved the file dozens of times. This is very alarming. Why has this happened, and is there a way to recover the lost edits?

Hannah · Answer

In that case, I don't think there's a way to recover those edits, @mdb282.

If they were never saved to Word or got lost in Word, then they never made it to your Dropbox account.

That means they cannot be recovered through Dropbox, but I would still suggest reaching out to Microsoft as well, in case they have an idea of what might have happened or how to fix it.

mdb282 · Answer

I did not confirm that the app was syncing after the update, but it appears that other files I had edited over the same two-day period I was editing the Word file in question did sync, so the app must have been running and syncing in general.

When I look at the file's version history it shows the last change as being right around the time of the OS update on April 13.

mdb282 · Answer

Yes. In every app, the file says the last edit was April 13, around the time I updated MacOS.