Issues uploading to Arduino using FTDI cable

Having trouble uploading to Arduino multiple times using an Adafruit FTDI cable. Clearly this is an issue with the Reset line, and I have used the famous 0.1uF cap between the RTS line on the FTDI cable and the reset pin on the Arduino. This however, does not solve the problem.

I am using a 16 MHz crystal with both pins connected to GND via 22 pF caps.

Once again, I can upload the sketch the first time correctly, and it works perfectly. If I try to upload another sketch, I have to unplug the USB and replug or pulse the Reset pin to GND.

I really have no idea what the problem is. I am using Mac OS X 10.9, and the Arduino IDE with all defaults set. The chip is an Arduino UNO with a pre-bootloaded image from Sparkfun.

Is there some software changes or drivers I need for mac?

Thanks!