This sentence is from an excellent book I'm reading. The "he" in the sentence is a man who has assaulted a woman and is worried she might tell someone about the assault:
"He could not help but be concerned that she might have discussed what had happened with some outsider."
This sentence suggests that something happened with "some outsider" instead of with the "he" of this sentence. The phrase we're concerned about is "with some outsider." It goes with "discussed," not "happened."
So, this sentence should read like this:
"He could not help but be concerned that she might have discussed with some outsider what had happened."
I wrote about the same error in this post.
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