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Generally if an applicant fails the civics/history examination or the reading/writing test, the USCIS will schedule one additional appointment to re-take the tests. If the applicant fails a second time, the naturalization case will be denied. The applicant may file a new case, but will have to start from the beginning in that process, including paying the application filing fees. The USCIS generally administers the tests in a non-aggressive way. For example, if someone misspells a word on the writing test, an examining officer may point to the word and ask "is there anything you would like to change about that?" The USCIS examining officer also may ask the applicant to write a different sentence. With the civics/history examination, an applicant needs only to correctly answer six out of ten questions, and so if a question is answered incorrectly, the examining officer simply will move on to the next question. (Note: no one gets extra credit for answering the first six questions correctly, and missing the correct answer to a couple of questions will not stand in the way of passing the test).

Something is wrong with this picture: ICE has neither the power nor a reason to detain a U.S. citizen. If you or your boyfriend's family have documents proving that he is a U.S. citizen, any competent immigration attorney should be able to get him released from the ICE custody rather fast.