Pandas Grouped Cumulative Count with Condition

I have a pandas df with Year, UserID, and Points. I'm trying to derive the fourth column below - a running count of the number of consecutive years a user has 0 points or less per year.

Ex Df

You can create a group column for consecutive positive or negative points first and then do a cumcount by the group:

neg_group = df.Points.le(0).diff().ne(0).groupby(df.UserID).cumsum()

neg_group
0    1
1    2
2    2
3    2
4    3
5    1
6    1
7    2
8    3
9    3
Name: Points, dtype: int64

df.groupby([df.UserID, neg_group]).cumcount()
0    0
1    0
2    1
3    2
4    0
5    0
6    1
7    0
8    0
9    1
dtype: int64