Duplicate openssl dgst -md5 -sign myKey.pem something.txt | openssl enc -base64 -A

Demonstrates how to duplicate the creation of an RSA signature produced by this OpenSSL command:

openssl dgst -md5 -sign myKey.pem something.txt | openssl enc -base64 -A

Download 32-bit Chilkat RSA ActiveX (.msi)

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Dim pkey As New PrivateKey

'  Load the private key from an RSA PEM file:
pkey.LoadPemFile "myKey.pem"

Dim success As Long

Dim pkeyXml As String

'  Get the private key in XML format:
pkeyXml = pkey.GetXml()

Dim rsa As New ChilkatRsa

'  Any string argument automatically begins the 30-day trial.

success = rsa.UnlockComponent("30-day trial")
If (success <> 1) Then
    Text1.Text = Text1.Text & rsa.LastErrorText & vbCrLf
    Exit Sub
End If

'  Import the private key into the RSA component:
success = rsa.ImportPrivateKey(pkeyXml)
If (success <> 1) Then
    Text1.Text = Text1.Text & rsa.LastErrorText & vbCrLf
    Exit Sub
End If

'  OpenSSL uses BigEndian byte ordering:
rsa.LittleEndian = 0

'  The resulting signature will be a Base64 string:
rsa.EncodingMode = "base64"

'  For simplicity, we're not loading
'  the data to be signed from a file.  We are instead simply
'  using a literal string value.
Dim strData As String
strData = "This is the text to be signed."

'  Hash the input using MD5, and then sign the hash:
'  Other valid hash algorithm choices are "md2" and "sha-1".
Dim base64Sig As String
base64Sig = rsa.SignStringENC(strData,"md5")

Text1.Text = Text1.Text & base64Sig & vbCrLf

MsgBox "Success!"