You don't say what you want to do,
this will work
SELECT
'button_flag' = SUM(CASE
WHEN (can_assign_supervisor = 1 AND
(SUM(ISNULL(auto_assign_cap, 0) - ISNULL(assigned_today_cap, 0)) > 0)
)
THEN 1
ELSE 0
END)
FROM processor
GROUP BY prsn_pk, can_assign_superviosor
WHERE prsn_pk = 36381
as will this:
SELECT
'button_flag' = SUM(CASE
WHEN (can_assign_supervisor = 1 AND
(ISNULL(auto_assign_cap, 0) - ISNULL(assigned_today_cap, 0)) > 0)
)
THEN 1
ELSE 0
END)
FROM processor
WHERE prsn_pk = 36381