Hey @GhostInTheCommu, I can help you with that!
There are many ways you can do that (both manually and automatically), but I’ll show one of the ways I find easier to handle.
First of all, create a Control Rig for your character and add two controllers, one for the head and one as a target. I’m not sure if you’re familiar with Control Rig, but you need to set the offset transform to be the same as the head bone. To do that, right-click the controller and select that option. Do the same for the target, then move it forward a bit so you can see it and reset from current (or you can simply add an offset to the shape, that way the transform stays the same as the head bone).
Then, add a Aim Node and a Two Bone IK and set the correct values for the Axis (both primary and secondary, this example is using the UE5 Manny) and connect the controllers you created to their respective nodes (target for the aim node and head for the IK). Now, if you move the target control, the head should follow it, and you can use that to test if the axis are correct if you’re unsure.
Now, all you have to do is add the Control Rig to sequencer. You can actually control it manually by moving the Target controller, but you can also Constraint it to Kakuna so it follows it automatically. To do that, go to the Animation tab on the left and find Constraints (the last option). With the Target control selected, set the option to Level Sequence and click on the + icon. Select Parent Constraint and it’ll ask you to select an Actor, so you can select the one you want.
To remove the offset, you can right-click the constraint and deselect “Maintain Offset”. The controller should snap to the same position as the actor you selected.
Now the Bug Catcher head should follow the position of the Kakuna 
You can also add variables/controllers to control the Weight of the IK so you can turn it on and off when needed.
I hope that helps, let me know if it works for you!
