Roofing in Milwaukee spends the heating season making ice. Months of attic heat melt the pack, the eave refreezes it, and water backs into a top-floor ceiling. Look from the alley. North slopes and lake-facing edges hold the dam longest. Cream City chimneys and old step flashing open in the same thaw. A low-slope porch roof ponds while the main gable is dealing with ice. Name which surface you actually have.
Thick icicles over the walk and a stain that grows on bitter days, not during rain, are the dam talking. Say if both a dam and lifted metal are present. Grit in the gutter is not a plains hail story. Pipe boots go brittle and leak when the thaw finally runs. A chimney crown that has crumbled dumps grit and lets water down the chase. Lifted edge metal from a lake blow is a different repair from the ice line.
Ventilation is the repeat offender. A bath fan in the attic and buried baffles will rebuild the dam after new shingles. Say what you know about the attic, including if you have never opened it. Deck that is soft under the eave is structure, not a surface swap. Snow sliding off a steeper addition onto a flat porch can puncture that porch. Describe the shape, not just the stain.
Scope includes ice protection at the eaves, chimney flashing, underlayment, and a path for meltwater. Debris has to leave a tight lot. Temporary cover matters when a thaw arrives before the work can finish. Keep people off an icy slope. Do not chip the dam into the shingles and call that a repair. If two units share the roof, say so before anyone tears off only one side.
Say ice dam, leak, or a blown edge, and say bungalow or duplex. Name the floor with the stain and whether the attic is warm. Milwaukee will keep feeding that eave as long as the heat is on. Call the number on this page.