Are you just wanting to overwrite one with the other, or do you want to synchronize two databases, each of which have received separate additions/deletions/modifications? If the former, I've always been able to just drag the ~/documents/Microsoft User Data/Office X Identities/Main Identity folder from one machine to another. The latter's a lot more tricky, and I'm not sure it's even possible. One possibility would be to sync the calendar with iCal (see this page for more info on that).

True synchronization of a calendar requires a server, which is why we're still stuck using Now Up-To-Date.

Another workaround is to upgrade to Office 2004, which would let you set up a shared project, which could then update both machines with common data. The shared project file would have to reside on a server somewhere (such as an iDisk). More info on how to do that can be found in Tom's eBook, Take Control of What's New In Entourage 2004.

Dori (not an Entourage deity, but I do live with one)

Why did I know Dori or Tom would be first to my aid?

What I really want is to be able to click a button and have Entourage automagically sync up with my laptop, like it (presumably) would with a PDA.

But I don't use a PDA right now, and I'd settle for something that automated overwriting the file on my laptop, as I grab it on my way out the door to a meeting or to go home from the office at night.

I assume I can Applescript that, although that would require me learning more than my meager Applescript foo currently permits.

Unfortunately, upgrading to Entourage 2004 is not an option right now, but I'll check out Tom's book for future reference.

I can't be the only person in the world who relies on a desktop/laptop setup like this; I'm surprised (well, not too surprised) that this sort of thing isn't a standard, built-in feature.

(I also can't believe that after over a decade of using Eudora and Now Up-to-Date I'm even contemplating using a—gasp!—Microsoft product, but...well, these are interesting times, n'est pas?)

It should be fairly straightforward to create an overwriting script, but I'm not going to try to do it myself because I haven't done much scripting in ages and I don't want to wave my hands, say "do this," and destroy all your data.

But... if the situation is that you'll always have your laptop at work, and you'll always want the two machines in sync, here's an idea: when you're at work, hook the laptop up to the desktop as a firewire target drive. Then, set the "Main Identity" folder on the desktop to point to the laptop. With this setup (and no, neither of us have tried it, and we're not 100% positive it'll work, but it should), you only have a single database, and it's always on the laptop. Of course, if you ever don't have the laptop at work you're SOL, but the upside is that you don't have to do anything at all regarding syncing--you'll always have the latest/greatest on the laptop.

As always, YMMV, take a backup (or two) before trying anything that could hurt your data, etc.

since i have not been able to figure out how to do this either, i just purchased one of those 256MB USB jumpdrives/thumbdrives/whatever-the-hell-they-call-them and transfer the OfficeX Identities folder nightly from desktop to laptop, then back again the next morning provided i actually did any work at home which, with the discovery of several new luxury potato vodkas, is happening less and less.