Should I pump at night if baby wont drain breast?

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Should I pump at night and if my baby sleeps through feedings? My breasts became so painfully engorged last night and when he ate he didn’t drain my breast like he usually does.

He slept for longer stretches last night, going up to 4 hours which he’s never done before.

He’s 10 days old. I try to wake him up to finish them but he seems uninterested and satisfied on what he ate and just wants to sleep.

He usually drains my breast with each feeding.