Sync Skype Chat History on Multiple Machines With Dropbox

Skype is awesome. We use it a ton here at Automattic, and it’s my main communication service for staying in touch with friends and family who are spread out all over the world. It’s also still the best text IM client out there. And now with the iPhone app, I can make int’l calls on mobile without thinking about it.

The one issue though I’ve had lately, is that I rely on Skype so much, that when I use a second machine I find myself looking through Skype chat history for a link or reference, only to realize that it’s stored locally on another machine.

In my quest to find an ideal backup solution, I’ve been testing Dropbox which allows you to sync files between multiple machines. So I took a crack at trying to get my Skype chat history to sync. A quick google search brought up this post which I followed:

Step 1) Quit the Skype application on all machines
Step 2) Move the "main" Skype chat history files to the Dropbox directory:
"mv ~/Library/Application\ Support/Skype ~/Dropbox/"
Step 3) Create a symlink from the original folder to the Dropbox folder:
"ln -s ~/Dropbox/Skype/ ~/Library/Application\ Support/Skype"
Step 4) On your secondary machines, remove the /Library/Application\ Support/Skype folder, and just insert the symlink:
"ln -s ~/Dropbox/Skype/ ~/Library/Application\ Support/Skype"

And it works ! One issue to be aware of: If you are logged-in and running Skype on multiple machines at once, you can get file conflicts and Dropbox will create secondary files – which kills the whole sync idea. So for this to work, you need to quit Skype before you plan on using it on another machine — which isn’t a bad idea anyway since leaving it open just means missed messages.

And lastly, I posted some of this to the Dropbox forum and one member there recommended a slightly different method where: “The original stays where it is. Without moving it, one creates a symlink. Its symlink goes into the Drobox folder.” I tried that method early on, and at least with Skype, the chat history kept getting written locally and never updating the Dropbox folder.

So for now this is working nicely for me. I do wonder if in the future Skype would ever offer up a secure way to store chat history with them. I also did see mention of a new service that tackles this issue for IM history in general called — looks interesting but haven’t tested so far as it’s Windows and Linux only.

For anyone thinking of trying the symlink method, as with anything like this, please backup your files before attempting this, as YMMV.