Ok I may be a little hyper sensitive as I had the start run capacitor go out back in the summer. My question is with the system running in heat mode should the condenser fan be running. Thermostat inside is set to 66 degrees and outside temp is in the low 30s with a wind chill making it feel like the mid 20's. Just not sure if this is normal or if there is some other issue.

Its a heat pump. It runs when it is below freezing. It is able to pull some heat out of the air all the way down to absolute zero, theoretically. Once the outside temperature gets ridiculously cold, the auxiliary electric heat will also come on to add additional heat to keep the house warm.

Thanks for replying. Pretty sure I am just overthinking it since I had issues earlier this year.

Majority of the time, on your normal plane Jane unit, the fan is on in heating mode unless you are in defrost mode.

Yep, that is correct.

Thats what I was wandering. Didnt want to damage the compressor by running it if the condenser fan was supposed to be running.

A heat pump will reverse itself when it senses back pressure from the fan. It thinks it is iced up. It will blow off heat to melt the ice, but the air handler side will not blow cold air into the house.

you could try to verify if there is a fan cycling control or pressure switch wired in to keep the fan on or off. A quick look at the units wiring schematic would give you an idea.