Gilde kicks in when you get low enough while maintaining a pitch between -10 to -60 degree and a velocity that's not more than 4km/s? I've had glides still work even though I went almost 4km/s.
Anyways, the speed will most likely be the issue as the whole artifical horizon turns red for pitch below -60, if you don't get that warning then be glad you get emergency dropped instead because otherwise you might smack into the planet : /
But it's way too easy to go too fast, normal SC works by having 75% throttle as sweetspot to keep the ETA at 6sec all the way which is maximum deceleration, the issue comes from someone having had the bright idea of making horizontal orbital flight go WAY past the SC speed near the planet.
Example being that you can go 200km/s near the planet, then a bit closer to it in high altitude 0 pitch orbital SC you can suddenly go 300km/s... My guess is that this leads to the breakage of the 75% sweetspot, I've had -45 degree approaches where 100% throttle was fine, and 50% led to overspeeding at glide and drop instead.
Doubt this will be fixed as I'd bet my 32mil Asp that this is working as intended
So to make approaches easier, try to guess your dive angle between -30 and -45 degree, target your landing place and keep the ETA at or above 7sec, unless you just wanna go for the surface, then you're on your own with guessing whenever you're too fast.
Or if your target is on the other side: flip upside down and go 0 pitch orbital SC while looking up until it comes in view, then as above.