So, so green LOL!

[VeloVT]

Not sure about "you only drop the chain if you try to shift down when you are already halfway up"--I've managed to drop mine twice in the past two weeks when shifting down at the beginning of the hill. Or does that just mean I need to adjust the front derailleur a bit?

I have a triple on my bike and it took me a long time to feel comfortable with it. A couple tricks to avoid dropping the chain (which I haven't done in a long, long time and I do use all three rings):

1. Adjustment is really important. If you're dropping a lot, go to the shop and tell them what's happening, and have them fiddle with the front derailleur.

2. It's not about where you are on the hill, per se, but how hard you're pedaling. It's very difficult to shift between front chainrings if you're really hammering -- this often will result in either your bike not shifting at all, or dropping a chain. You need to let up for a few revolutions while you shift. This is much more important in the front than in the back, where you can shift pretty well even when powering up a hill. I read an explanation of this somewhere, and I don't remember the fine points, but basically it has to do with chain tension, which is greater in the front.

3. It takes a little while to get a feel for exactly how far you need to push the lever and for how long to get a clean shift in the front. Upshifting will have a different rhythm than downshifting too. For me, to shift into my 52 requires a very aggressive push -- to shift back down into 42 cleanly, I need to do a very quick little click that's half as long (in seconds) -- or less -- as the upshift. If I hold it longer the chain ends up overshifting a bit and doesn't sit cleanly on the chainring, and has to be "trimmed." (Little mini up/down shifts until it's quiet). Similarly, to shift into my granny gear (30) cleanly I can't linger on the shifter -- it needs to be one very quick click.

Good luck!!!

Oh -- and if you DO drop a chain -- you can often sweep it back up while riding with well-timed upshift.