Mac OSX Arduino with FTDI: upload only works once per USB plug/unplug

I have this arduino Duemillanove with FTDI chip. It works fine on my PC. I uploaded code several times in a row. No problem. I updated the bootloader to UNO/optiboot a long time ago. But when I am using in on my Mac OSX, it only works once per USB plug/unplug. After first upload, the code works and I can open serial port on my Mac and see data printed to the monitor. But, I just can't upload a second time without disconnecting it and connecting it again. There is nothing connected to it.

Any idea what I may have not done to make it work?

What's the error?

You might drop to a terminal and do "lsof | grep usbserial" and see if avrdude (or another process) is grabbing the serial port.

If it's the same problem I'm having, AVRDUDE lowers RTS to reset the Arduino, but never raises it again, so next time it doesn't work.

I also have an older computer that had Arduino 1.6.1 that works normally, and updating to 1.6.5 also works. Newer computer that only had 1.6.5 doesn't.

Thanks guys. I've not touched the computer since then. I am using Arduino 1.6.5-r5 and the error was not in sync. I'll take another look. Last time I tried to log on it is frozen (updated to el capitan).