i agree that if you aren't really measuring what you eat, the tracker telling you that you are under is kind of useless info.
if you really don't want to weigh and measure at all, do the bikini diet plate [1/2 plate is veg, 1/4 protein and 1/4 starch]. and if you aren't using a plate it basically means half of what you eat a vegetable, 1/4 of what you eat a protein and starchy things can make up the final 1/4. try it out. if this works for you, great, keep it up.
but if that breakdown doesn't get you the results you need, you may need to make time to measure and track. think of it like if you broke your arm - you'd make extra time to get dressed in the morning and wrap up your cast so you could shower. in other words, you aren't where you need to be so you need to spend some time learning the how and where and why. and haul out the cups and spoons and scale and measure. pay extra attention to the portion sizes and how they look for foods that you eat frequently. note the serving sizes of general kinds of food [breads and bagels should be an ounce, cheese should be an ounce, meat should be 3-4 oz, fruits and veggies should be about 3-5 oz].
-google first. ask questions later.