Answer first, context after
Why is upstairs freezing in winter when it was boiling all summer?
Same house, same physics, opposite result. Warm air rises, but in winter your ducts, insulation, and air leaks conspire differently: heated air escapes through the attic above the second floor, leaky ducts lose their warmth before reaching the far rooms, and the stack effect pulls cold outside air in low while pushing your paid-for heat out high. The fixes overlap heavily with the summer ones.
If your second floor roasts in July and shivers in January, congratulations, you own a completely normal two-story house. It feels contradictory, warm air rises, so upstairs should be the warm floor, and sometimes it is. But several forces work against the second floor in winter, and in many homes they win.
The attic sits directly on top of it. The second floor’s ceiling is the house’s boundary with a cold attic, and every gap in that insulation bleeds heat from upstairs first. Downstairs enjoys a heated buffer above it, which is the whole second floor. Upstairs gets the sky.
The stack effect runs the wrong direction for you. Warm air rising does not stay put; it leaks out through the attic’s penetrations, can lights, duct chases, the attic hatch, and every cubic foot that escapes up high pulls a cubic foot of cold outside air in through gaps down low. The house becomes a slow chimney, exhausting your heat through the top floor’s ceiling all night.
The ducts lose their cargo en route. Supply runs to upstairs rooms are the longest in the house, and in winter a leaky or poorly insulated duct crossing a cold attic delivers air that left the furnace warm and arrives merely mild. The rooms at the end of those runs, the same ones that suffer in summer, get shortchanged in both seasons, which is the tell that ducts, not equipment, are the story.
The fix list, in payback order: seal the duct leaks, $189 to $980, which pays on both the gas bill and the summer electric bill. Seal and insulate the attic-floor penetrations, unglamorous work any insulation contractor handles, and we will say so when it is the better first dollar than anything on our menu. Check register balancing, because dampers set for summer often need a winter position. And for a second floor that no amount of balancing rescues, the zoned answer is the same one summer suggests: its own system for the floor, controlled by the people who actually sleep up there.
Still stuck? That's what the truck is for.
The diagnostic is $89, waived when you book the repair, with a written flat price before any work starts.