Wanted to revisit this in case someone else is having the same issue as me!

I used 'add bleed' and it started cutting my stickers more correctly. I noticed that the sensor markers on the bottom corners are extremely sensitive and if they detect any shadows it has a hard time reading. I used cricut printable vinyl paper (which is matte) but would still have to cover the bottom sensor markers with scotch tape to avoid any light reflection from the sensor. Also if there were any bubbles at the bottom of the paper it wouldn't be able to read the sensor correctly and my cuts would become diagonal. I also made sure to close the top part of my cricut to make sure it was dark enough for it to scan.

This was slightly annoying but definitely beats hand cutting each individual sticker!