Kalin, I would recommend having the tiller turning prior to lowering it into the ground. Also if you are being pushed by the tiller it would be good to have rear wheel weights. You didn't mention if you had any on. Also the type of tires you have also makes a big difference. In the past we ran a 110 with a 33 tiller with both extensions and never had issues with front weight however if we ran without rear weights you had better hang on.