I file in 2 states that have direct pay online for extension payment (they accept the Fed extension), so I checked and you can do the payment directly with Massachusetts here. Guess you'd have to manually tell the TT program what you paid if it's done outside the program; I don't use the online version so not sure about that. https://www.mass.gov/service-details/learn-about-extensions-for-filing-and-paying-massachusetts-inco...
