Sometimes you luck out your first year - I first got a permit in January, and it was good through March of the following year. I think it depends on the timing.

And OP, I parked with an expired permit on the first of the month last year, on a street that's regularly patrolled for parking, and wasn't ticketed - just one anecdote and not an official policy (and the city might want the income more this year), but there's occasionally leniency.