God's Activities Through the Other Tribes and Their Disobedience (Judges 1:21-36).
‘ And the children of Benjamin did not drive out the Jebusites who inhabited Jerusalem. But the Jebusites dwelt with the children of Benjamin in Jerusalem to this day.'
This seems to mean that they could have driven them out of the part of Jerusalem and its surrounds that they occupied, but that they did not. They were disobedient.
In Joshua 15:63 we read that Judah could not drive the Jebusites out of their part, which probably included the fortress. Thus the successful attack in Judges 1:8 may simply be referring to the capture of the lower city, or it may be that, due to the absence of the Jebusites on a military expedition, they were then able to take the upper city and sack it, but not to retain it because at the time they had to move on. After which the Jebusite soldiers returned. It is noticeable that there is no mention of driving anyone out there. The purpose was not possession. Then when the fighting men of the Jebusites returned they retook the city and from then on were invulnerable in the upper citadel.
But the main purpose of this verse is to point out the disobedience of Benjamin in contrast with the obedience of Judah and Simeon. This is then to be followed by the disobedience of Manasseh, Ephraim, Zebulun, Asher and Naphtali, and the failure of Dan. Reuben and Gad were of course across the river beyond the Jordan.
Issachar is not mentioned and may possibly be seen as united with Zebulun, like Simeon with Judah. Note that they were also praised in the song of Deborah (Judges 5:15), yet omitted in Judges 5:18 where those who were faithful to the call are mentioned, (even though they were one of them), and are not mentioned in the prose account in Judges 4. Again presumably they were seen as one with Zebulun (see also Deuteronomy 33:18 where they are included in the blessing of Zebulun).