It really needs to be sorted. This becomes apparent if you give it an offset as the window size (for datetimes) instead of an integer.
Sample Data
import pandas as pd
n = 6
df = pd.DataFrame({'date': pd.date_range('2018-01-01', '2018-01-03', periods=n),
'val': range(n)})
df = df.set_index('date')
When in order:
df.rolling(2, on='date').sum()
date val
0 2018-01-01 00:00:00 NaN
1 2018-01-01 09:36:00 1.0
2 2018-01-01 19:12:00 3.0
3 2018-01-02 04:48:00 5.0
4 2018-01-02 14:24:00 7.0
5 2018-01-03 00:00:00 9.0
When unordered it doesn't sort and respect the date ordering.
df.sample(frac=1, random_state=123).rolling(2, on='date').sum()
date val
1 2018-01-01 09:36:00 NaN
3 2018-01-02 04:48:00 4.0
4 2018-01-02 14:24:00 7.0
0 2018-01-01 00:00:00 4.0
2 2018-01-01 19:12:00 2.0
5 2018-01-03 00:00:00 7.0
Now if you want a 2 Day rolling sum, you'd do something like:
df.rolling(window='2D', on='date').sum()
date val
0 2018-01-01 00:00:00 0.0
1 2018-01-01 09:36:00 1.0
2 2018-01-01 19:12:00 3.0
3 2018-01-02 04:48:00 6.0
4 2018-01-02 14:24:00 10.0
5 2018-01-03 00:00:00 15.0
But when not sorted, you get an error indicating that you should have sorted first:
df.sample(frac=1, random_state=123).rolling(window='2D', on='date').sum()
ValueError: date must be monotonic