Sealing the shingle to the object can be accomlished with a roofing sealant available at menards lowes etc.
Repair leaky roof in winter.
Roof leaks must be repaired from the outside to ensure the problem is corrected.
The shingles can be warmed up with a propane torch.
Electric tape works well but it must be applied before the winter season begins a pickaxe works well with risk to further damage to your roof.
Perhaps placing tube on furnace duct so air heats pre cut tube inside of home then climb up ladder and seal area keeping the sealant warm and easily caulk able.
If a leak is difficult to find enlist a helper and go up on the roof with a garden hose.
Look for cracks in the base of flexible rubber flashing or broken seams in metal varieties of vent pipe flashing.
For loose or damaged shingles remove them by pulling the nail out and scraping glue from underneath the shingles before replacing with new ones.
For flat roofing look for cracks.
To repair a leaking roof with curled shingles straighten the shingles with a heat source like a hair dryer and reattach them with asphalt roof cement or compound.
If there is ice on the roof and it can be cleared do so.
However when it is not practical to climb up on the roof to fix a leak such as during the winter months you can repair a leaky roof temporarily from the inside if you can determine where the leak is occuring from the underside of your roof.
2plumbing vent boots and roof vents.
For example soak the downhill side of a chimney first then each side then the top on both sides.
This can be done by several methods.
Check plumbing vent boots and roof vents if water is entering from that area to cause the leaking roof.
Locate the leaking source and search for the damaged or missing shingles and make a list of the areas to be repaired.
The secret to caulking in winter time is to heat the sealant in the tube.
Roof leaks are confusing to diagnose.
Isolate areas when you run the hose.
The rubber gasket that surrounds the vent pipe could be rotted.
Make use of the flame carefully on the curled shingle edges.
Using salt on the roof edge may be the safest and easiest way.