This study seeks to establish the feasibility of assai as a moderating term in more cases than is typically assumed. Since evidence of concurrent competing definitions for the term assai exists from the mid- to late-18^th century, understanding and putting into practice a composer’s indications according to his own understanding of the term becomes murky where the word assai is concerned during and beyond the time when the two definitions exist concurrently. Through investigation of musical scores, examining such features as ornamentation, the relative brilliance of the work, tonality, meter, and structure, the characteristics of a piece of music that are crucial to navigating the multivalent qualities of the word assai are identified and tested against the actual musical content of examples from works of J. S. Bach, Domenico Scarlatti, W. F. Bach, J. C. F. Bach, Johann Friedrich Agricola, C. P. E. Bach, W. A. Mozart, F. J. Haydn, Ludwig van Beethoven, Frédéric Chopin, and Franz Liszt.