It doesn't get cloudy. It can start to rain and I put the weather settings on overcast, but the sky does not change, the only sky I ever had was some light clouds. The rain works though, just not the clouds. Also the weather forecast you see when you're in a session remains the same, it always says 'sunny'. Also the temperature doesn't change.
I see these sometimes, but not always. The forecast consistently does not seem to be updated when you change the weather settings. Once I ran a test session with the sky starting out "clear" but there were clouds. The next time I did it again to see if it would repeat, but it worked properly, starting out clear and then progressing to clouds and rain. In both cases, however, the sky maintained a "partly cloudy" rather than overcast appearance throughout the subsequent heavy storm and after it ended. It was a bit weird seeing just a scattering of clouds while rain poured down and heavy mist appeared on the track.