> echo 'text_to_cypher' | openssl enc -e -des-ede3-cbc -k 'b2aec78eb50e04f2a60b9efa20b82c903e3cad4f3bd2027g' -iv 00000000 -nosalt | openssl enc -base64 That echo command will append a LF (x'0a') byte (if this is a conventional UNIX or Linux system, or Cygwin, etc, and you're running under one of the standard shells). Do you have that byte in the value of your "cleartext" variable in the Java code? You failed to supply that. (Also, the single-quote characters are unnecessary, unless you're running a very odd shell.) The value of the -k argument you're passing to "openssl enc" ends with "g", which is not a hexadecimal digit; the rest of the value appears to be hexadecimal. But it's not clear why you're using -k anyway. Perhaps you mean to use -K (uppercase K, with an actual hexadecimal argument)? -- Michael Wojcik Technology Specialist, Micro Focus