The Moabites were generally enemies of Israel, and thus God excluded all Moabites, and their descendents for 10 generations, from entering "the assembly of the Lord". This is Deuteronomy 23:3:
The woman Ruth, however, was a Moabite who became the wife of the Israelite named Boaz. This is itself doesn't present a problem, since Ruth apparently never entered the assembly. The problem, though, is that Ruth and her husband Boaz were (via their son Obed) ancestors of King David, one chosen of God and a great king of Israel. This is Ruth 4:18-22:
This would make David a descendant of a Moabite, and thus he should have been excluded from the great role that he took on. He certainly entered "the assembly". One could say that God made an exception, though this is rather unsatisfying.
Another solution is to claim that the genealogy is not complete, but rather skips some generations, so that 10 generations actually passed between Ruth and David. However, it's clear that Boaz was Obed's actual father, and it's clear that Jesse was David's actual father, so this gap must occur entirely between Obed and Jesse. I'm not aware of any reason to believe that Obed isn't Jesse's actual father, and so I don't see this solution as very plausible either.
Finally, a reader suggests to me that the rule only applied to the male lineage - i.e. someone would count as a Moabite if their father was a Moabite, but not if their mother was. Apparently, this is clearer in the original Hebrew.
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