If it has sufficient power to lift the pin off the hitch, it should be able to lift to full extent of the legs. Sounds to me more like it has reached its maximum height and that isn't high enough to level the trailer on the site.
If you haven't done so already, drop the pin back on the hitch, take the weight off the landing gear, adjust them for a lot less drop and make up the difference between the feet and ground with some cribbing. You should be able to gain at least a foot of lift provided you have the right blocks to do it safely.
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'11 Cougar 326MKS loaded with mods
'12 Ford F250 SuperCab 6.7 PowerStroke Diesel
Amateur Radio: KD2IAT (146.520) GMRS: WQPG808 (462.675 TPL 141.3)
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