So I’m a little unsure of what drop box will do in this scenario. My ancient macbook fell over yesterday and the only way to get it to work again was restore from a time machine back up. That worked fine but probably missing a day or two. I also have a drop box folder for photos and stuff. So what will happen when I connect to dropbox.

1) Laptop folder will update with missing stuff from after the restore point – hurrah.
2) Laptop will stay the same but drop box folder in cloud will delete the stuff not on my laptop – boo.

1

To be sure I’d restore the machine with the internet disconnected, move all the file out of you old dropbox folder (update dropbox if required also). Then re-connect to the net and let drop box re-download everything

It should sync the two together and keep newest versions of files (your option 1), but I’ve used the above method to make sure nothing is overwritten by accident.

It hasn’t been connected to the net yet. I might try copying what I have to another non linked folder and then see if it will get it all again.

It should see what is newest and maintain that so will be option 1.

Dropbox has version control though so you could restore the latest versions of files anyway, no matter what happens on initial connection.

As above there’s a few fail-safes. If it finds two versions it’ll copy both. You can also go back through version histories via the website. I’d still copy the folder as it saves some hassle.