Find the Lawman does not progress Merged

I received the quest Find the Lawman. Went to the biome and proceeded to talk to him. As soon as I did The same quest popped up again saying to talk to him. After I progressed through the dialogue the original quest I got changed to reflect what he wanted me to do but the second never did and remained at "talk to the lawman".

After completing the shooting quest completely and finishing the original quest the second quest never progressed. Now when I go talk to the lawman he simply says that he has no more to teach me and I cannot continue the quest to report it back to the reporter lady.