I feel like I have to bend forward to feel like he is sitting upright...it feels like he could flip out backwards, what am I doing wrong?

The shoulder straps may be too loose. If you are in an upright ‘normal’ stance, i.e., not leaning forward or backward to balance the added weight of your child on your body, then you have the carrier correctly positioned. If not, tighten the shoulder straps so that your baby is being held closer to your body. With their legs down around your waist and their body strapped close to yours, your child is secure in the carrier.