Detailed answer
Factors That Change The Recommendation
Overlaying shingles saves money short-term - that's the appeal. But it also hides the roof deck, which matters a lot if there are already leaks, soft spots, or aging flashing underneath. You're basically betting that nothing's wrong under there. That's a bet some homeowners regret.
A second layer adds weight, can shorten the new material's life, and makes future leak tracing way harder (now you've got two layers of shingles to detective through). Most reputable contractors recommend tear-off because it lets them install fresh underlayment, ice-and-water protection, new flashing, and actually inspect the decking. Overlay is rarely a good fit if the current roof is wavy, brittle, leaking repeatedly, or already at the code-allowed layer limit. Be skeptical of any contractor who suggests overlay when those things are true.
If You're In California Or New Jersey
New Jersey homes usually benefit from tear-off when ice barriers, decking checks, and ventilation upgrades are needed. California homes need careful review of heat-aged shingles and low-slope transitions before any overlay conversation - lots of CA roofs that look fine on top have aged out underneath.