I have to replace top shock mounts in my '04 Bonneville. Started today because of the good weather. Have to work outside!

First one of the lower shock mount bolts broke, no one open today that has one, maybe tomorrow probably Monday. Then I couldn't get the air line out of the left shock, came out with great difficulty, never had one come out so hard. Had to actually use pliers on the line. Never had to use pliers before. Changed the top mount and can't get the air line back in! The fitting just won't go over the nipple far enough to catch the clip.
This is the dilemma - the air line installation.
I cannot get the air line back in the shock. The line does not appear damaged, none of the parts appear damaged.
I notice that the air line has two small 'o' rings on it, is this normal?
Even with one of the 'o' rings off it won't go back in.
I'm getting older, could this be my problem?

Should I change the shocks?

Any ideas, other than get a younger person to work on it?

thanks,

when i replaced my struts i broke the line on both sides those things are a pain. after calling everyone i could think of to get the right stock stuff, i found this air line to tire valve type kit. basically replaces everything and i just put air in it every six months or so.

Monroe Shock Absorber Air Hose Kit-AK29 - Advance Auto Parts

if yours look like mine they need replaced

i did the same kit. routed it inside my trunk for easy access. i put in about 70lbs in summer to raise the rear end up just a hair, and about 60 in winter for better weight distribution.

didnt look at the pressure, i just set it so it has a little front to back rake when nothing is in the trunk

No desire to change the air line system to a manual type.
Finally found an old pair of machinists wide mouth clamping pliers that pushed it back in!
Still wonder why it went in so hard but it is back in place.

i would check the connections and strut bellow for leaks by spraying some soapy water around and looking for bubbles, thats how i lost my compressor, little leak made it run quite a bit and they are like 300 bucks