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The reply was more aligned to any new viewers to the thread. Although it was originally listed back in 2016, as you've so graciously pointed out, the problem is clearly still ongoing.
This happened to us recently. The dipstick breaks around 2" from the lower end at the plastic gauge section. If you don't fish out the broken end it will cause a blockage, which would explain why your dipstick won't insert those last 2 inches.