Under FAA regulations, the answer depends strictly on the class of airspace you are occupying. In controlled airspace (Classes A, B, C, D, and E), it is strictly illegal to fly in Instrument Meteorological Conditions (IMC) without a filed IFR flight plan and a specific ATC clearance. However, in uncontrolled airspace (Class G), the regulations are technically different. While 14 CFR 61.3(e) requires a pilot to hold an instrument rating to act as Pilot in Command in conditions less than VFR minimums, there is no specific federal regulation that mandates an IFR flight plan or ATC clearance for flight in Class G airspace. This means that a qualified pilot in a properly equipped aircraft could technically fly through a cloud in Class G without talking to anyone. However, doing so is considered extremely dangerous and highly discouraged by the aviation community, as there is no separation service provided by ATC in Class G. If an accident were to occur, the FAA would likely cite the pilot for "Careless or Reckless Operation" under 14 CFR 91.13. Therefore, while a "legal loophole" may exist in remote uncontrolled areas, professional pilots always file a plan.