Signtool.exe succeeds but zero signatures are added to the file

Question

I'm writing a custom CNG provider (Key Storage Provider) to allow signing using our private HSM API in Signtool.exe I implemented the APIs in my CNG provider and successfully installed in my Windows 10 system.

Command:

signtool.exe sign /v /debug /f cert.cer /csp "Sample Key Storage Provider" /k "keyid" /t http://timestamp.digicert.com /fd sha256 helloworld.exe

Signtool.exe succeeds with return code 0 but ends up adding no signatures to the file.

Verify Output:

signtool.exe verify /v /pa helloworld.exe

Verifying: helloworld.exe
Signature Index: 0 (Primary Signature)
Hash of file (sha256): 3338A11DDAB9CBB7B39E65C30F235C2DF8EDE17BB5BE759A3213D25EC286F390

Signing Certificate Chain:
    Issued to: Sample Certificate Authority
    Issued by: Sample Certificate Authority
    Expires:   Fri Feb 07 21:37:36 2070
    SHA1 hash: 2B5B37DADFCBD018BDB2789176A69708FFCA25E0

        Issued to: Sample test certificate
        Issued by: Sample Certificate Authority
        Expires:   Thu May 28 13:40:10 2020
        SHA1 hash: A679DF5E89B9C23E57E89AEB434CA98230F52DC3

The signature is timestamped: Sun Mar 29 16:44:01 2020
Timestamp Verified by:
    Issued to: DigiCert Assured ID Root CA
    Issued by: DigiCert Assured ID Root CA
    Expires:   Sun Nov 09 17:00:00 2031
    SHA1 hash: 0563B8630D62D75ABBC8AB1E4BDFB5A899B24D43

        Issued to: DigiCert SHA2 Assured ID Timestamping CA
        Issued by: DigiCert Assured ID Root CA
        Expires:   Tue Jan 07 05:00:00 2031
        SHA1 hash: 3BA63A6E4841355772DEBEF9CDCF4D5AF353A297

            Issued to: TIMESTAMP-SHA256-2019-10-15
            Issued by: DigiCert SHA2 Assured ID Timestamping CA
            Expires:   Wed Oct 16 17:00:00 2030
            SHA1 hash: 0325BD505EDA96302DC22F4FA01E4C28BE2834C5

SignTool Error: No signature found.

Number of files successfully Verified: 0
Number of warnings: 0
Number of errors: 1

However, when i look at the Digital Signatures tab in the file properties, it does show an entry. When i select the entry it say "no signature was present in the subject".

What am i missing here?

Answer 1

signtool.exe sign 
   /v 
   /debug 
   /f cert.cer 
   /csp "Sample Key Storage Provider" 
   /k "keyid" 
   /t http://timestamp.digicert.com 
   /fd sha256 
   helloworld.exe

The documentation says when using /f SignCertFile :

• if the file is a .pfx , you must use /p to specify the password
• if the file does not contain private keys, you must specify
  • /csp CSPName
  • /kc PrivKeyContainerName

I see you do specify /csp :

/csp "Sample Key Storage Provider"

But you don't specify /kc .

I do see you specify /k - which is nothing.