At first in your example, you are on the 090 radial FROM the VOR and at that instant happen to be travelling towards it. You could be tracking in any direction and would still be on the 090 radial from the aid.
After crossing the aid you will be on the 270 radial from the aid.
The radial you're on is by definition described from the station ie they radiate FROM the aid.
Since the CDI will be centred if the OBS is selected to the radial you're on OR the one opposite the next problem is to determine which side of the VOR you're on.
If you're on the same side of the VOR as the radial then the FROM flag will show. If the other side of the beacon then the TO flag is shown.
Bear in mind a TO or FROM flag will show whether or not you're located on the OBS selected radial. Which one is displayed depends on whether you're in the same hemisphere as the OBS selected radial.
The TO or FROM flag & its display relative to the hemisphere stems from what would happen if you held the same heading as the radial. If you were on the 270 radial & also set 270 as a heading then you would track FROM the aid.
Ergo, if you were on the opposite side of the VOR - still with the 270 HDG then you must track TO the aid.
Don't forget that if you were on the opposite side of aid compared to the 270 radial then you would be on the 090 radial.
Hence '...track TO the VOR on the 090 radial...' or in a more abbreviated form '090 radial TO the VOR' then after passing overhead you would be '...tracking on the 270 radial FROM the aid.'