mjhjmtu

It seems that on macOS since Mojave (OSX 10.14.3), the -ssl option had been deprecated from RSA Utils (rsautl command) on it's default OpenSSL.

$ sw_vers
ProductName: Mac OS X
ProductVersion: 10.14.3
BuildVersion: 18D42
$ 
$ openssl version
LibreSSL 2.6.5

Where can I get these update releases info? I googled the net but couldn't find them...

If I try to use -ssl option then it returns the help as an error. But the -ssl option is still there.

$ openssl rsautl -encrypt -pubin -inkey id_rsa.pub.pkcs8 -ssl -in test.txt -out test.txt.enc
Usage: rsautl [options]
-in file input file
-out file output file
-inkey file input key
-keyform arg private key format - default PEM
-pubin input is an RSA public
-certin input is a certificate carrying an RSA public key
-ssl use SSL v2 padding
-raw use no padding
-pkcs use PKCS#1 v1.5 padding (default)
-oaep use PKCS#1 OAEP
-sign sign with private key
-verify verify with public key
-encrypt encrypt with public key
-decrypt decrypt with private key
-hexdump hex dump output

But in the manual, the -ssl option doesn't appear.

$ man openssl 
...
RSAUTL
 openssl rsautl [-asn1parse] [-certin] [-decrypt] [-encrypt] [-hexdump] [-in
 file] [-inkey file] [-keyform der | pem] [-oaep | -pkcs | -raw] [-out file]
 [-pubin] [-sign] [-verify]
...

I understand that since SSL v2 is no longer good to use, they deprecated the -ssl option.

But I need some kind of confirmation about this so to let my client know and change their protocol to send encrypted files.

I noticed that the man was updated today (my time, Jan 29, 2019, Tokyo).

$ man openssl | tail -1
BSD January 29, 2019 BSD

So I thought that Apple just forgot to update the -help, but even in the Mojave release notes there was no info about it.

Where can I get info of these changes and/or report to update the --help?

I think I found where. And seems that it wasn't the Apple's issue but LibreSSL's OpenBSD issue. I'm sorry Apple.

• 
  OpenBSD for LibreSSL @ GitHub

In the latest commit's source code below, there still was the -ssl option.

• "rsautl.c" (Line 321 / Commit 19a8bdc)

I think this is the place to see the changes and report an issue.