If you're having trouble getting the bead on the tire to seat, you can use a strap (or even a belt) to assist. Take the wheel/tire off the machine (if it isn't already) and wrap the strap around the diameter of the tire. When you pull the strap tight it should cause the side walls to push out and get them to pop onto the rim as you apply air. Once both sides of the tire pop up onto the rim, stop applying air and take the strap off, then finish pressuring the tire.
Some thing to do that will ease this process along:
Wash the rim and wheel in soapy water.
You can use soapy water to act as a lubricant to help get the bead to pop onto the rim.
You can use grease to help get a good seal on the bead (I do this all the time on all tires).
You will almost certainly need pressurized air to get the bead to pop onto the rim. A bike pump usually will not work for this.
If all else fails you can likely get a local independent tire shop to mount the tire for you for less than $10.
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