After more than a decade practicing immigration law in Illinois, I’ve worked closely with many citizenship attorneys in Chicago on naturalization cases that people often assume are automatic. From the outside, citizenship can look like the final, easiest step. In reality, it’s one of the stages where past mistakes surface most clearly—and where careful legal judgment matters more than most applicants realize.
One of the first naturalization cases that reshaped my approach involved a permanent resident who had lived in the U.S. for years without incident. The application itself seemed routine, but during our review, a brief overseas trip from years earlier raised questions about continuous residence. The applicant hadn’t thought twice about it and almost omitted it entirely. That detail alone could have delayed the case or triggered additional scrutiny if it had come up unprepared during the interview. Experiences like that are why I no longer treat citizenship filings as simple paperwork exercises.
I’ve also seen how criminal history—sometimes decades old—can complicate things unexpectedly. In one case, a client assumed a minor arrest from early adulthood was irrelevant because it never led to jail time. During the naturalization interview, it became the focal point of the conversation. We were able to address it because we had already gathered court records and discussed how to explain it clearly and honestly. I’ve watched similar cases fall apart when applicants were told to “just file” without fully understanding how closely these histories are examined at the citizenship stage.
Chicago presents its own set of realities. Local USCIS interviews tend to be thorough, especially around travel history, tax compliance, and moral character. I’ve prepared clients who were surprised by how detailed the questioning became, particularly when their green card had been based on marriage or employment. Attorneys who regularly handle citizenship cases here tend to prepare people for that level of scrutiny, rather than assuming the interview will be brief or procedural.
A common mistake I encounter is timing. Some people rush to apply as soon as they believe they’re eligible, without considering whether unresolved issues—like inconsistent tax filings or extended trips abroad—should be addressed first. In my experience, waiting and filing cleanly is often far better than filing quickly and inviting complications. Citizenship is permanent; a denial can have consequences that reach well beyond the application itself.
After years of handling these cases, I’ve come to see naturalization as less about forms and more about narrative. Every applicant has a story, and the government will examine how consistent that story has been over time. The attorneys who do this work well are the ones who know how to identify weak points early, prepare clients honestly, and slow the process down when caution is warranted. In a city as busy and exacting as Chicago, that measured approach is often what makes the difference between a smooth oath ceremony and an avoidable setback.