Cliffhanger is tube less compatible so the tolerance is probably a bit tighter. 
However, just to make sure we got the baseline covered:

What tire lever were you using? I’ve broken some cheapo levers. I always use 
Pedros or Park. 

When you took the tire off, you did move the bead to the center channel of the 
rim bed? Meaning, you broke the bead ALL the way around the rim first, then 
made sure the bead was in the center groove before sticking the tire lever in 
there. Then started at the valve stem and worked your way around (for mounting 
the tire, you of course start at the opposite the stem). 

Pushing the valve stem up may give you a tiny bit more wiggle room. 

You may also want to just set it up tubeless. Can’t remember the last time I 
got a flat on my tubeless bikes. But just the other day, front tire on my tubed 
Hunq was flat. The may be getting some tubeless rims for that in the future. 

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