Remember Chechnyan war 1994-95 and the storming of Grozny. Several convoys against Grozny ended in a slaughter (bloodbath) of Russian conscripts in the storming of Grozny. It looks as the same could happen know in Kiev.
https://en.wikipedia.org/wiki/First_Chechen_War
One problem was the communications and the call in of the air support. Russian army have a lot of communications vehicles there special radios are for air force communications and the call in of combat aircraft and helicopters (serial 600?). A Russian brigade have around 50 communications vehicles. They are distributed to the Battalion battle group (BLT). Many of them had no educated personnel to communicate (in Chechnya). They had also to communicate without crypto. Poor education of signalists. Vehicles were also transported without signalists because they lacked it. It also ment that radio traffic with the higher command in Rostov were done without crypto. The best signalist was the Russian enemy in this case, the Chechen army (educated signalists). They red the radio traffic very well, with big Russian losses.
In the Syrian war the last years they had the same problem. Russia had also to tow the newbuilt communications vehicles from landing ships in Tartus there the most important vehicles had broken chilling systems, together with the other problems.
In the past was much of the communications equipment produced in Ukraine. Ukraine know a lot of this.
I am shore that the US intelligence knew much about what happening. During the Hungarian war 1956 could intelligence listen to tank and combat vehicles radio traffic 1000 km away.
One other thing is the bad precision of the combat aircraft and the helicopter weapons.
Remember the 2018:s other 100 cruise missiles against Syria. They hit direct.
