> I was signing a message with the smime tool and following command line
> ...
> and I was unable to verify the signature using the commercial toolkit
>
> OpenSSL:
>
> 30 21 30 09 06 05 2B 0E 03 02 1A 05 00 04
> 14 14 44 0A B6 53 49 25 48 25 A8 02 A3 5C
> 7C 1A 8C D1 14 F9

This looks correct to me:

  SEQUENCE ($21) {
    SEQUENCE ($09) {
      OID ($05)
      NULL ($00)
    }
    OCTETSTRING ($14)
  }

>
> PKCS #1:
>
> 30 21 30 1F 06 05 2B 0E 03 02 1A 05 00 04 
> 14 14 44 0A B6 53 49 25 48 25 A8 02 A3 5C
> 7C 1A 8C D1 14 F9

This doesn't:

  SEQUENCE ($21) {
    SEQUENCE ($21) {
      OID ($05)
      NULL ($00)
      OCTETSTRING ($14)
    }
  }

since AlgorithmIdentifier is defined as

AlgorithmIdentifier ::= SEQUENCE {
    algorithm     OBJECT IDENTIFIER,
    parameters    ANY DEFINED BY algorithm OPTIONAL 
}

The OCTETSTRING which probably holds the signature
is not a parameter of the algorithm.

Just my two pence

Robert

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