Big time.

I had the same thing happen to me on a very hilly ride a couple of years ago (I also tend to ride toes-down sometimes.)

My advice, for what it is worth, is take all the time you need now to let it heal. This can be a very nagging, hard to heal injury. That area doesn't get a lot of blood flow, so it can it be very slow to heal - and painful as all hell.

I would also ice it regularly, and have a fit-pro examine your bike fit (my seat was too high).

Mine is starting to flare up again now, and I am watching it closely. I am icing it pre-emptively.

Another focus point when riding hills is RELAX, LIGHT FEET. We all tend to exert a whole bunch of pressure on the pedals, but this doesn't make you go up the hill faster. Turning the cranks does. So whenever I'm climbing, I tell myself to relax and to lighten up my feet. In fact, whenever you climb, you should never put too much more pressure on your feel than was there at the bottom of the climb.

I gotta add my 2 cents into this cause I have beat my prob. I know it may sound corny but it worked for me and I am writing this so that others may have the same result.

In my blog for those that have been following I have been battling an achilles prob for over 3 weeks and after going to 2 sessions with an acupuncturist I have it beat. Two things I Rx for the prob. one is rest (duh!) and for me that IS hard but also after going to the doc for it it's cured, here is what she did:

Using a little vacuum cup she went around and found the blood constriction areas around the foot and ankle by sucking the skin and pulling the blood to the surface; like we did as kids sucking the skin to make a kind of hikkie. It was cool to see where the blood was pooling around the leg and where the injury really was. After that she placed the needles to strategic points of the muscles and connected electrodes to the pins. Then she gave me the control box to the electrodes (3 dials, one for each pair), and said I should control the muscle reflexes/controlled spasams as the current went through. 20min. of this and the muscles felt SO good after that it was like I had a brand new leg! I felt like a run that night finally, but I didn’t of course Despite the no pain or anythig, she told me to sit and do nothing for as long as I can and to elevete the ankle inflammation despite no probs. with it, and use heat for treatment NOT ICE. She said the ice constricts the blood from cleaning the inflamed area out, just use IB.

Additionally I have also found from some research on Gordos site that the prob is common in the achilles with triathletes for two reasons. One, cause we run and the shoes can get bad. Duh! Like we know that one. But the other just skipped me in the analysis. That being, the cleats on the toe clips of the bike. Gordo says the following as a coach:

“With your Achilles Tendon (AT)– check for lateral rock in your bike shoes. Nearly all my athletes’ AT issues can be traced back to the bike — specifically old shoes or speedplay pedals (Gale’s warning from long ago). You need lateral stability or pronation in the foot results in strain on the AT.

Question: What is it about old shoes that makes them a problem? I currently use old Carnacs and Speedplay pedals. Plaatjes had suggested that I get a different pair of pedals.

Answer: That was the exact set-up that I had when I experienced a recurring AT irritation. Here’s what happens…

The shoe is able to rock
The foot pronates through the bottom of the shoe stroke
Torque is pasted up the lower leg
Your calves take it until they are fatigued then the AT is overloaded
This problem cleared in 72 hours when I bought new shoes and went to look pedals. When your irritated leg is clipped into the shoe have someone hold your heel/toe and see if they can rock the shoe. If you have a lot of rock then I would bet that this is the source of your AT pain.”

Good luck and I hope this may help someone. It did me and I am SO thankful!!