StringEncryptor beans: [lazyJasyptStringEncryptor] encrypt("jasypt-secret") twice with the starter's default encryptor: L3j9uk0JtxuSgfME2mgcEdp4DqxtdXsrHnLaQ2dXyIEOEwzHncjtN3MJm0praytC QcEwZQiMm5z1a1VIf17Gkbr9e0eunC0Riuy7tbvYMZ4zVMylXVoBek699CM2LRog same ciphertext both times: false (random salt and IV per call) db.password=ENC(...) + jasypt.encryptor.password=master-key: environment: db.password = jasypt-secret bound: DbProperties[url=null, username=null, password=] same ENC(...) value, wrong master key: started: no; EncryptionOperationNotPossibleException: null same ENC(...) value, no master key configured: started: no; IllegalStateException: either 'jasypt.encryptor.password', one of ['jasypt.encryptor.private-key-string', 'jasypt.encryptor.private-key-location'] for asymmetric encryption, or one of ['jasypt.encryptor.gcm-secret-key-string', 'jasypt.encryptor.gcm-secret-key-location', 'jasypt.encryptor.gcm-secret-key-password'] for AES/GCM encryption must be provided for Password-based or Asymmetric encryption outside Spring, org.jasypt only, algorithm PBEWITHHMACSHA512ANDAES_256, 1000 iterations, random salt+IV: decrypt(ciphertext) = jasypt-secret