We recently found a pipe that had been insulated below and above the roofline. The portion of the pipe between the upper and lower roof surface was not insulated at all:
Here’s what the pipe section looked like when it was removed:
This pipe lasted over 30 years before it started to weep. That gouge you see is where the water that leaked through the top of the roof penetration pooled. It’s a Good Engineering Practice to run the insulation COMPLETELY through the interstitial space.
Make sure you check the work of your installers – thankfully the diligence of the maintenance team at this facility caught this before it let loose!