Entry 1 sense Webster, 1913 Congratulatory /kən-grăch'-əl-ət-ôrˌ-ē/ · Con·grat·u·la·to·ry · IPA /kənˈɡɹæt͡ʃələˌtɔɹi/ 01 a. Expressive of sympathetic joy; as, a congratulatory letter. 1. Expressive of sympathetic joy; as, a congratulatory letter.