If you are having trouble with the pouch covering too much of your shoulder you can fold it. Start with the fabric closest to your shoulder and fold it in half, under towards your neck. I hope I explained it good enough for you to understand. My son is also 4 months old and I put him in the cradle position. You need to put him in a more upright position so he is able to look out. Then you can tuck the outer pouch rail under his arm. That will help him to be able to see out. Also I have to cross my sons legs for him to fit in the pouch. Let me know if you need more help.