In Judges 1-2, we see many things that are encouraging from the children of Israel as they are driving out of the Promised Land the Canaanites and those who possess what God intends for them to possess. Then at the end of Judges 6 we see the great victories of God's people turn into the compromises of God's people.
But Manasseh did not take possession of Beth-shean and its villages, or Taanach and its villages, or the inhabitants of Dor and its villages, or the inhabitants of Ibleam and its villages, or the inhabitants of Megiddo and its villages; so the Canaanites persisted in living in that land.
It came about when Israel became strong, that they put the Canaanites to forced labor, but they did not drive them out completely.
Ephraim did not drive out the Canaanites who were living in Gezer; so the Canaanites lived in Gezer among them.
Zebulun did not drive out the inhabitants of Kitron, or the inhabitants of Nahalol; so the Canaanites lived among them and became subject to forced labor.
Asher did not drive out the inhabitants of Acco, or the inhabitants of Sidon, or of Ahlab, or of Achzib, or of Helbah, or of Aphik, or of Rehob.
So the Asherites lived among the Canaanites, the inhabitants of the land; for they did not drive them out.
Naphtali did not drive out the inhabitants of Beth-shemesh, or the inhabitants of Beth-anath, but lived among the Canaanites, the inhabitants of the land; and the inhabitants of Beth-shemesh and Beth-anath became forced labor for them.
Then the Amorites forced the sons of Dan into the hill country, for they did not allow them to come down to the valley;
yet the Amorites persisted in living in Mount Heres, in Aijalon and in Shaalbim; but when the power of the house of Joseph grew strong, they became forced labor.
The border of the Amorites ran from the ascent of Akrabbim, from Sela and upward.
What we see is the seed of incomplete obedience that will be the fruit of pain for generations to come. If we would keep short accounts with the Lord and recognize that He loves us but does not tolerate our sin because He knows that our sin creates great pain in the long run we would be so much better off. The Lord comes in Judges 2 and makes the pronouncement that the Canaanites and those whom they have tolerates will be like a thorn in their side. The Canaanites will plunder them rather than vice versa.
At the end of Judges 2, we see God's mercy AGAIN.
Then the LORD raised up judges who delivered them from the hands of those who plundered them. 2:16
When the LORD raised up judges for them, the LORD was with the judge and delivered them from the hand of their enemies all the days of the judge; for the LORD was moved to pity by their groaning because of those who oppressed and afflicted them. 2:18
As God gave hope through the Judges we also see that every time a Judge died the people went right back to the sin rather than running to the LORD - Jehovah.