The Homophonic Substitution cipher is a classical substitution cipher designed to replace each plaintext character with one of several possible ciphertext symbols, reducing the effectiveness of frequency analysis. While its exact origins are unclear, it became widely studied in the 16th and 17th centuries and was employed in diplomatic and military communications to obscure letter frequencies. In this cipher, high-frequency letters like E or T are assigned multiple ciphertext equivalents, while less frequent letters may have only one. For example, using a simple homophonic mapping for the plaintext “HELLO,” the letter H could be encoded as 14, E as 3 or 7, L as 19 or 21, and O as 26. Encrypting “HELLO” might then yield 14 7 19 21 26, with each occurrence of L potentially choosing a different code. Decryption involves mapping each ciphertext symbol back to its original letter according to the agreed-upon key table. The Homophonic Substitution cipher strengthens classical substitution methods by distributing plaintext frequency across multiple ciphertext symbols, making statistical attacks more difficult, especially on short texts. While it is not secure against modern cryptanalysis, it historically demonstrates the principle of flattening letter frequency distributions and highlights early attempts to increase cipher robustness. Practicing with inputs like “HELLO” illustrates how a single plaintext word can produce varied ciphertext sequences depending on the homophonic assignments, emphasizing the cipher’s strategy of frequency masking and symmetric reversibility when the key table is known.