In the Second Circuit, whether one trademark is likely to be confused with another is measured by the eight-factor test that Judge Henry Friendly set out in Polaroid Corp. v. Polarad Electronics Corp. Because likelihood of confusion is a fact-laden inquiry, summary judgment is treated as the exception rather than the rule, yet the Circuit affirms it for defendants case after case. The reason is a structural one that this guide unpacks in detail: some Polaroid factors turn on objective, fixed inputs a court can weigh on a paper record, while others depend on contested evidence of intent or real-world confusion that usually belongs to a jury. We walk each factor as it actually behaves under Rule 56, explain the mixed-question doctrine that lets a court decide the ultimate confusion question as a matter of law, and identify the recurring fact pattern that produces a no-confusion ruling. The article adds a fully worked hypothetical, a movant-and-non-movant drafting playbook, a section on how the type of confusion alleged reshapes the analysis, a frequently asked questions section, and extensive cross-references to related UpLaw resources.