Thanks for the advice so far.
I asked my father to help me measure/judge the distance between my eye and the scope when I had it shouldered. He noticed that I was shouldering the rifle very low (only the bottom of my jaw was on the cheek piece), causing me to have to "look down" into the scope. According to him, this position resulted in my eye being about 3 inches behind the scope, but my forehead being only 1 inch behind.
After practicing shouldering the rifle correctly* (my cheek is actually on the cheek piece), my father help me reposition the scope. Hopefully I've corrected the problem. But if/when I upgrade scopes, I think I'll still opt for something with a little more eye relief.
* or what I'm assuming is closer to correct
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