Used he to work into the night?

他以前总是工作到深夜吗？

youdao

She used to work into the night.

过去她常工作到深夜。

youdao

Did he use to work into the night?

他以前总是工作到深夜吗？

youdao

These were the operations that were most often crammed in at the end of the day, forcing a surgeon and nurses to work late into the night.

FORBES: Magazine Article

To compensate I would work late into the night and every weekend.

FORBES: Does Working From Home Work For You?

Mr Bell said nothing would happen in the immediate future because there was a lot of work to do and night flights would come into operation over the next three to five years.

BBC: Dunsfold-based air ambulance to fly at night