In a recent little project I made a little java app which did this:
1. Check if a URL was present on the windows clipboard.
2. If so, connect to and request it be made smaller.
3. Once the smaller URL was returned it would auto put it on windows clipboard again ready for pasting.

This turned out to be quite simple (I liked using a bit of regex to extract the made tiny url) until I wanted to add 2 more features:
1. Have it work in the system tray.
2. Have it catch the key-combo when minimised.

This wasn't quite as simple as you would think. The java prog is of course isolated from the native system by the JVM. For a novice working with native code and java turned out to be quite a challenge. I first tried to figure out JNI. Don't get me started on that. The tutorial on isn't that clear (for me) and JNI caused me a lot of headaches.

Anyway, I finally solved the problem by letting java start up a native app as a process and using streams from that app to deal with with the native events. I unfortunately didn't have time to implement this solution.

Well, this story is not really why I am posting. I just wanted to post the alternatives to I came across while developing the above app:

I still prefer TinyURL although I also have found some good use for URLCutter which lets you make custom urls.

jpwain says:

Along those lines, I've also found the TinyURL bookmarklet to be tremendously handy (as opposed to, as you suggest, running an app in the system tray).

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