Year round, it is almost always sunny in the mornings. But, in summer (May - Aug) the thunderstorms build up in the West and spill over the mountains around 3:00 p.m. where they cool the air by about 20º and then clear out around 5:00 - 6:00 p.m. If you live in Teller County, the rains are almost daily from 11:00 a.m. - 5:00 p.m. oftentimes with heavy hail and temperature drops of over 30º. Summers in the mountains are usually cold and wet.

Unfortunately, this past summer and so far this fall, have been unusually wet and snowy. Dreary and tiresome. It's unusual, but depressing, nonetheless.
Colorado Springs is usually sunny in the winter, so if there is snow, it melts pretty quickly, especially on roads and sidewalks. It can also get up around 70º in February, but it's followed by our snowiest month, March. November and April are also snowy. I do recall many Christmas days where the kids would play outside with their new toys in tee shirts and jeans.

And there have been more dry, brown Christmasses than white ones. White meaning actually snowing on the day. There may be snow on the ground, but sunny. There is also virtually no humidity and the air is thin, so snow melts quickly.
Sunny days are the speakers interpretation. Usually it means, some sun at some point during any given day. Which in this case would mean 300 days with at least some sun--maybe only ten minutes, but that counts--and 65 days of no sun. But there are not 300 days of crystal clear blue skies with not a single cloud. That just doesn't happen. Ten minutes of sun counts as a whole, sunny day.
