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It's not likely the o-rings will seal if it isn't pushed in flush. This would be bad.
Suggest putting a little soapy water on the o-rings to let them slide better into their grooves.
Of course, this all assumes that you have looked into the head opening to make certain there aren't any bits of rubber from the plug boots or plastic from the old cracked tube causing clearance issues.
The plug boots don't really look too bad from the pics, but you don't want them arcing to ground and denying the spark energy to the plug.
From the pics, I'd say you could roll the dice and re-use them, but that could lead to an issue of rough running, cels, etc. If you get any of this, then replace them.
Cheers!
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