Dip stick tube insertion depth

[Big Red 2006]

While trying to find a oil leak i came across this. Does the tube need to be inserted to the ridge or just till the o ring is covered?

 

[Bob4x4]

Should go in till it bottoms,unbolt it before trying to seat it.Be careful when you try to line up the bracket again,the tube can break

 

[Big Red 2006]

I took both bolts off and tried to push it in. It only made it half way to the ridge. Not sure if it needs to go all the way. Was only able to get 1 bolt back which makes me think the line is bent from who ever previously installed it.