As you can see, the first time an animation is loaded it does not have a transition, but it rather jolts down. This only happens the first time, after that its fine.
Am just using humanoid.Animator:LoadAnimation():Play() for this
I was able to achieve what I wanted by playing the animation as soon as the player joins and then instantly stopping it. Will mark this as the solution for anybody who stumbles upon this in the future
EDIT: Play the animations from a LocalScript and not a Server Script. I forgot that animations replicate. Playing from the localscript doesnt have this stutter.