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I am trying to determine the best method for code-signing an executable using Bouncy Castle, managed code, or un-managed code from C#. Since CAPICOM is now deprecated, I imagine one of the SignerSign methods from mssign32.dll is the best way to go if it needs to be done unmanaged.
This answer (https://stackoverflow.com/a/3952235/722078) seems close, but it produces a .p7m file, which, while appearing to be the right size, will not run correctly (obviously renamed to .exe before running).
The solution given by the question-asker here (API/Library to replace signtool.exe) seemed promising and managed, but like Tom Canham mentions in the comments below, "it appears that this is for signing enveloped messages. Authenticode -- the code-signing that signtool does -- is different, which is why the EXE doesn't run after the signing." I receive the same error that Tom does when I sign using either the question-asker's solution or the previously referenced Bouncy Castle solution.
The only option that I have not attempted yet is given here (https://stackoverflow.com/a/6429860/722078), and while it looks promising, I am not positive that it uses "authenticode" code-signing as opposed "enveloped message" code-signing. This answer also has the benefit of not using the CAPICOM interop methods which are now deprecated, so I imagine I will report back on my results using this method today. If this is the best option, could anybody out there speak to the differences between SignerSign, SignerSignEx, and SignerSignEx2 functions that are exported from mssign32.dll? I have read that SignerSignEx2 should be used with Windows 8 and higher...
Long story short, I would like to replicate the ability of signtool.exe to sign an executable given a .exe file, .pfx file, and password like so:
signtool sign /f cert.pfx /p password application.exe
I am looking for the best option to programmatically code-sign an executable (PE if it matters) using authenticode signing, and I would prefer to use bouncy castle or managed code if possible, although I will use something unmanaged if it works and is not currently deprecated.
Thanks!
574
As far as I can tell, SignSigner and SignSignerEx are available as of Windows XP, which is the oldest operating system I care to support. Because I do not need to worry about Windows App Store publication, this answer is limited to SignSigner and SignSignerEx, although the import for SignSignerEx2 is very similar to SignSignerEx, and I wouldn't expect it to cause any problems.
The following class allows you to sign an executable with a .pfx by calling:
SignWithCert(string appPath, string certPath, string certPassword, string timestampUrl);
It also allows you to sign an executable with a certificate from a key store by calling:
SignWithThumbPrint(string appPath, string thumbprint, string timestampUrl);
If you want to sign using a cert installed into a key store, you may need to update FindCertByThumbPrint(string thumbPrint) to check more key stores than I care to check. 99.5% of the time, our customers sign with a .pfx and not with a thumbprint.
For the sake of illustration, SignWithCert() utilizes SignerSignEx and SignerTimeStampEx, while SignWithThumbPrint() utilizes SignerSign and SignerTimeStamp.
They're easily interchanged. SignerSignEx and SignerTimeStampEx give you back a SIGNER_CONTEXT pointer and allow you to modify the behavior of the functions with the dwFlags argument (if you're signing a portable executable). Valid flag options are listed at here. Basically, if you pass 0x0 as the dwFlags to SignerSignEx, the output will be identical to just using SignerSign. In my case, I imagine I'll be using SignerSign because I don't believe I need a pointer to the signer context for any conceivable reason.
Anyway, here is the class. This is my first time posting code here, so I hope I haven't broken it in formatting.
The code works as expected, and the executable runs fine and signed, BUT the binary output of the signature block differs slightly from the binary output of signtool.exe (in that test, a timestamp was used by neither tool). I attribute this to the fact that signtool.exe appears to use CAPICOM for signing and this uses Mssign32.dll, but all in all, I am pretty pleased with it in the initial set of tests.
The error handling obviously needs improvement.
Thanks to GregS and everybody out there who's posted code samples previously.
Here's the relevant stuff. I will update this block with comments and improvements when I get the chance to do so.
Update 1: Added somewhat better error handling and comments, along with some reformatting of the thumbprint in FindCertByThumbprint(string thumbprint) to allow the cert to be found on Windows 8 and Windows 10 (public preview). Those OSes wouldn't return a match when spaces were left in the thumbprint, so I am now fixing them before searching.
using System;
using System.Runtime.InteropServices;
using System.Security.Cryptography;
using System.Security.Cryptography.X509Certificates;
namespace Utilities
{
internal static class SignTool
{
#region Structures
[StructLayoutAttribute(LayoutKind.Sequential)]
struct SIGNER_SUBJECT_INFO
{
public uint cbSize;
public IntPtr pdwIndex;
public uint dwSubjectChoice;
public SubjectChoiceUnion Union1;
[StructLayoutAttribute(LayoutKind.Explicit)]
internal struct SubjectChoiceUnion
{
[FieldOffsetAttribute(0)]
public System.IntPtr pSignerFileInfo;
[FieldOffsetAttribute(0)]
public System.IntPtr pSignerBlobInfo;
};
}
[StructLayoutAttribute(LayoutKind.Sequential)]
struct SIGNER_CERT
{
public uint cbSize;
public uint dwCertChoice;
public SignerCertUnion Union1;
[StructLayoutAttribute(LayoutKind.Explicit)]
internal struct SignerCertUnion
{
[FieldOffsetAttribute(0)]
public IntPtr pwszSpcFile;
[FieldOffsetAttribute(0)]
public IntPtr pCertStoreInfo;
[FieldOffsetAttribute(0)]
public IntPtr pSpcChainInfo;
};
public IntPtr hwnd;
}
[StructLayoutAttribute(LayoutKind.Sequential)]
struct SIGNER_SIGNATURE_INFO
{
public uint cbSize;
public uint algidHash; // ALG_ID
public uint dwAttrChoice;
public IntPtr pAttrAuthCode;
public IntPtr psAuthenticated; // PCRYPT_ATTRIBUTES
public IntPtr psUnauthenticated; // PCRYPT_ATTRIBUTES
}
[StructLayoutAttribute(LayoutKind.Sequential)]
struct SIGNER_FILE_INFO
{
public uint cbSize;
public IntPtr pwszFileName;
public IntPtr hFile;
}
[StructLayoutAttribute(LayoutKind.Sequential)]
struct SIGNER_CERT_STORE_INFO
{
public uint cbSize;
public IntPtr pSigningCert; // CERT_CONTEXT
public uint dwCertPolicy;
public IntPtr hCertStore;
}
[StructLayoutAttribute(LayoutKind.Sequential)]
struct SIGNER_CONTEXT
{
public uint cbSize;
public uint cbBlob;
public IntPtr pbBlob;
}
[StructLayoutAttribute(LayoutKind.Sequential)]
struct SIGNER_PROVIDER_INFO
{
public uint cbSize;
public IntPtr pwszProviderName;
public uint dwProviderType;
public uint dwKeySpec;
public uint dwPvkChoice;
public SignerProviderUnion Union1;
[StructLayoutAttribute(LayoutKind.Explicit)]
internal struct SignerProviderUnion
{
[FieldOffsetAttribute(0)]
public IntPtr pwszPvkFileName;
[FieldOffsetAttribute(0)]
public IntPtr pwszKeyContainer;
};
}
#endregion
#region Imports
[DllImport("Mssign32.dll", CharSet = CharSet.Unicode, SetLastError = true)]
private static extern int SignerSign(
IntPtr pSubjectInfo, // SIGNER_SUBJECT_INFO
IntPtr pSignerCert, // SIGNER_CERT
IntPtr pSignatureInfo, // SIGNER_SIGNATURE_INFO
IntPtr pProviderInfo, // SIGNER_PROVIDER_INFO
string pwszHttpTimeStamp, // LPCWSTR
IntPtr psRequest, // PCRYPT_ATTRIBUTES
IntPtr pSipData // LPVOID
);
[DllImport("Mssign32.dll", CharSet = CharSet.Unicode, SetLastError = true)]
private static extern int SignerSignEx(
uint dwFlags, // DWORD
IntPtr pSubjectInfo, // SIGNER_SUBJECT_INFO
IntPtr pSignerCert, // SIGNER_CERT
IntPtr pSignatureInfo, // SIGNER_SIGNATURE_INFO
IntPtr pProviderInfo, // SIGNER_PROVIDER_INFO
string pwszHttpTimeStamp, // LPCWSTR
IntPtr psRequest, // PCRYPT_ATTRIBUTES
IntPtr pSipData, // LPVOID
out SIGNER_CONTEXT ppSignerContext // SIGNER_CONTEXT
);
[DllImport("Mssign32.dll", CharSet = CharSet.Unicode, SetLastError = true)]
private static extern int SignerTimeStamp(
IntPtr pSubjectInfo, // SIGNER_SUBJECT_INFO
string pwszHttpTimeStamp, // LPCWSTR
IntPtr psRequest, // PCRYPT_ATTRIBUTES
IntPtr pSipData // LPVOID
);
[DllImport("Mssign32.dll", CharSet = CharSet.Unicode, SetLastError = true)]
private static extern int SignerTimeStampEx(
uint dwFlags, // DWORD
IntPtr pSubjectInfo, // SIGNER_SUBJECT_INFO
string pwszHttpTimeStamp, // LPCWSTR
IntPtr psRequest, // PCRYPT_ATTRIBUTES
IntPtr pSipData, // LPVOID
out SIGNER_CONTEXT ppSignerContext // SIGNER_CONTEXT
);
[DllImport("Crypt32.dll", EntryPoint = "CertCreateCertificateContext", SetLastError = true, CharSet = CharSet.Unicode, ExactSpelling = false, CallingConvention = CallingConvention.StdCall)]
private static extern IntPtr CertCreateCertificateContext(
int dwCertEncodingType,
byte[] pbCertEncoded,
int cbCertEncoded);
#endregion
#region public methods
// Call SignerSignEx and SignerTimeStampEx for a given .pfx
public static void SignWithCert(string appPath, string certPath, string certPassword, string timestampUrl)
{
IntPtr pSignerCert = IntPtr.Zero;
IntPtr pSubjectInfo = IntPtr.Zero;
IntPtr pSignatureInfo = IntPtr.Zero;
IntPtr pProviderInfo = IntPtr.Zero;
try
{
// Grab the X509Certificate from the .pfx file.
X509Certificate2 cert = new X509Certificate2(certPath, certPassword);
pSignerCert = CreateSignerCert(cert);
pSubjectInfo = CreateSignerSubjectInfo(appPath);
pSignatureInfo = CreateSignerSignatureInfo();
pProviderInfo = GetProviderInfo(cert);
SIGNER_CONTEXT signerContext;
SignCode(0x0, pSubjectInfo, pSignerCert, pSignatureInfo, pProviderInfo, out signerContext);
// Only attempt to timestamp if we've got a timestampUrl.
if (!string.IsNullOrEmpty(timestampUrl))
{
TimeStampSignedCode(0x0, pSubjectInfo, timestampUrl, out signerContext);
}
}
catch (CryptographicException ce)
{
string exception;
// do anything with this useful information?
switch (Marshal.GetHRForException(ce))
{
case -2146885623:
exception = string.Format(@"An error occurred while attempting to load the signing certificate. ""{0}"" does not appear to contain a valid certificate.", certPath);
break;
case -2147024810:
exception = string.Format(@"An error occurred while attempting to load the signing certificate. The specified password was incorrect.");
break;
default:
exception = string.Format(@"An error occurred while attempting to load the signing certificate. {0}", ce.Message);
break;
}
}
catch (Exception e)
{
// do anything with this useful information?
string exception = e.Message;
}
finally
{
if (pSignerCert != IntPtr.Zero)
{
Marshal.DestroyStructure(pSignerCert, typeof(SIGNER_CERT));
}
if (pSubjectInfo != IntPtr.Zero)
{
Marshal.DestroyStructure(pSubjectInfo, typeof(SIGNER_SUBJECT_INFO));
}
if (pSignatureInfo != IntPtr.Zero)
{
Marshal.DestroyStructure(pSignatureInfo, typeof(SIGNER_SIGNATURE_INFO));
}
if (pProviderInfo != IntPtr.Zero)
{
Marshal.DestroyStructure(pSignatureInfo, typeof(SIGNER_PROVIDER_INFO));
}
}
}
// Call SignerSign and SignerTimeStamp for a given thumbprint.
public static void SignWithThumbprint(string appPath, string thumbprint, string timestampUrl)
{
IntPtr pSignerCert = IntPtr.Zero;
IntPtr pSubjectInfo = IntPtr.Zero;
IntPtr pSignatureInfo = IntPtr.Zero;
IntPtr pProviderInfo = IntPtr.Zero;
try
{
pSignerCert = CreateSignerCert(thumbprint);
pSubjectInfo = CreateSignerSubjectInfo(appPath);
pSignatureInfo = CreateSignerSignatureInfo();
SignCode(pSubjectInfo, pSignerCert, pSignatureInfo, pProviderInfo);
// Only attempt to timestamp if we've got a timestampUrl.
if (!string.IsNullOrEmpty(timestampUrl))
{
TimeStampSignedCode(pSubjectInfo, timestampUrl);
}
}
catch (CryptographicException ce)
{
// do anything with this useful information?
string exception = string.Format(@"An error occurred while attempting to load the signing certificate. {0}", ce.Message);
}
catch (Exception e)
{
// do anything with this useful information?
string exception = e.Message;
}
finally
{
if (pSignerCert != IntPtr.Zero)
{
Marshal.DestroyStructure(pSignerCert, typeof(SIGNER_CERT));
}
if (pSubjectInfo != IntPtr.Zero)
{
Marshal.DestroyStructure(pSubjectInfo, typeof(SIGNER_SUBJECT_INFO));
}
if (pSignatureInfo != IntPtr.Zero)
{
Marshal.DestroyStructure(pSignatureInfo, typeof(SIGNER_SIGNATURE_INFO));
}
}
}
#endregion
#region private methods
private static IntPtr CreateSignerSubjectInfo(string pathToAssembly)
{
SIGNER_SUBJECT_INFO info = new SIGNER_SUBJECT_INFO
{
cbSize = (uint)Marshal.SizeOf(typeof(SIGNER_SUBJECT_INFO)),
pdwIndex = Marshal.AllocHGlobal(Marshal.SizeOf(typeof(uint)))
};
var index = 0;
Marshal.StructureToPtr(index, info.pdwIndex, false);
info.dwSubjectChoice = 0x1; //SIGNER_SUBJECT_FILE
IntPtr assemblyFilePtr = Marshal.StringToHGlobalUni(pathToAssembly);
SIGNER_FILE_INFO fileInfo = new SIGNER_FILE_INFO
{
cbSize = (uint)Marshal.SizeOf(typeof(SIGNER_FILE_INFO)),
pwszFileName = assemblyFilePtr,
hFile = IntPtr.Zero
};
info.Union1 = new SIGNER_SUBJECT_INFO.SubjectChoiceUnion
{
pSignerFileInfo = Marshal.AllocHGlobal(Marshal.SizeOf(typeof(SIGNER_FILE_INFO)))
};
Marshal.StructureToPtr(fileInfo, info.Union1.pSignerFileInfo, false);
IntPtr pSubjectInfo = Marshal.AllocHGlobal(Marshal.SizeOf(info));
Marshal.StructureToPtr(info, pSubjectInfo, false);
return pSubjectInfo;
}
private static X509Certificate2 FindCertByThumbprint(string thumbprint)
{
try
{
// Remove spaces convert to upper. Windows 10 (preview) and Windows 8 will not return a cert
// unless it is a perfect match with no spaces and all uppercase characters.
string thumbprintFixed = thumbprint.Replace(" ", string.Empty).ToUpperInvariant();
// Check common store locations for the corresponding code-signing cert.
X509Store[] stores = new X509Store[4] { new X509Store(StoreName.My, StoreLocation.CurrentUser),
new X509Store(StoreName.My, StoreLocation.LocalMachine),
new X509Store(StoreName.TrustedPublisher, StoreLocation.CurrentUser),
new X509Store(StoreName.TrustedPublisher, StoreLocation.LocalMachine) };
foreach (X509Store store in stores)
{
store.Open(OpenFlags.ReadOnly);
// Find the cert!
X509Certificate2Collection certs = store.Certificates.Find(X509FindType.FindByThumbprint, thumbprintFixed, false);
store.Close();
// If we didn't find the cert, try the next store.
if (certs.Count < 1)
{
continue;
}
// Return the cert (first one if there is more than one identical cert in the collection).
return certs[0];
}
// No cert was found. Return null.
throw new Exception(string.Format(@"A certificate matching the thumbprint: ""{0}"" could not be found. Make sure that a valid certificate matching the provided thumbprint is installed.", thumbprint));
}
catch (Exception e)
{
throw new Exception(string.Format("{0}", e.Message));
}
}
private static IntPtr CreateSignerCert(X509Certificate2 cert)
{
SIGNER_CERT signerCert = new SIGNER_CERT
{
cbSize = (uint)Marshal.SizeOf(typeof(SIGNER_CERT)),
dwCertChoice = 0x2,
Union1 = new SIGNER_CERT.SignerCertUnion
{
pCertStoreInfo = Marshal.AllocHGlobal(Marshal.SizeOf(typeof(SIGNER_CERT_STORE_INFO)))
},
hwnd = IntPtr.Zero
};
const int X509_ASN_ENCODING = 0x00000001;
const int PKCS_7_ASN_ENCODING = 0x00010000;
IntPtr pCertContext = CertCreateCertificateContext(
X509_ASN_ENCODING | PKCS_7_ASN_ENCODING,
cert.GetRawCertData(),
cert.GetRawCertData().Length);
SIGNER_CERT_STORE_INFO certStoreInfo = new SIGNER_CERT_STORE_INFO
{
cbSize = (uint)Marshal.SizeOf(typeof(SIGNER_CERT_STORE_INFO)),
pSigningCert = pCertContext,
dwCertPolicy = 0x2, // SIGNER_CERT_POLICY_CHAIN
hCertStore = IntPtr.Zero
};
Marshal.StructureToPtr(certStoreInfo, signerCert.Union1.pCertStoreInfo, false);
IntPtr pSignerCert = Marshal.AllocHGlobal(Marshal.SizeOf(signerCert));
Marshal.StructureToPtr(signerCert, pSignerCert, false);
return pSignerCert;
}
private static IntPtr CreateSignerCert(string thumbprint)
{
SIGNER_CERT signerCert = new SIGNER_CERT
{
cbSize = (uint)Marshal.SizeOf(typeof(SIGNER_CERT)),
dwCertChoice = 0x2,
Union1 = new SIGNER_CERT.SignerCertUnion
{
pCertStoreInfo = Marshal.AllocHGlobal(Marshal.SizeOf(typeof(SIGNER_CERT_STORE_INFO)))
},
hwnd = IntPtr.Zero
};
const int X509_ASN_ENCODING = 0x00000001;
const int PKCS_7_ASN_ENCODING = 0x00010000;
X509Certificate2 cert = FindCertByThumbprint(thumbprint);
IntPtr pCertContext = CertCreateCertificateContext(
X509_ASN_ENCODING | PKCS_7_ASN_ENCODING,
cert.GetRawCertData(),
cert.GetRawCertData().Length);
SIGNER_CERT_STORE_INFO certStoreInfo = new SIGNER_CERT_STORE_INFO
{
cbSize = (uint)Marshal.SizeOf(typeof(SIGNER_CERT_STORE_INFO)),
pSigningCert = pCertContext,
dwCertPolicy = 0x2, // SIGNER_CERT_POLICY_CHAIN
hCertStore = IntPtr.Zero
};
Marshal.StructureToPtr(certStoreInfo, signerCert.Union1.pCertStoreInfo, false);
IntPtr pSignerCert = Marshal.AllocHGlobal(Marshal.SizeOf(signerCert));
Marshal.StructureToPtr(signerCert, pSignerCert, false);
return pSignerCert;
}
private static IntPtr CreateSignerSignatureInfo()
{
SIGNER_SIGNATURE_INFO signatureInfo = new SIGNER_SIGNATURE_INFO
{
cbSize = (uint)Marshal.SizeOf(typeof(SIGNER_SIGNATURE_INFO)),
algidHash = 0x00008004, // CALG_SHA1
dwAttrChoice = 0x0, // SIGNER_NO_ATTR
pAttrAuthCode = IntPtr.Zero,
psAuthenticated = IntPtr.Zero,
psUnauthenticated = IntPtr.Zero
};
IntPtr pSignatureInfo = Marshal.AllocHGlobal(Marshal.SizeOf(signatureInfo));
Marshal.StructureToPtr(signatureInfo, pSignatureInfo, false);
return pSignatureInfo;
}
private static IntPtr GetProviderInfo(X509Certificate2 cert)
{
if (cert == null || !cert.HasPrivateKey)
{
return IntPtr.Zero;
}
ICspAsymmetricAlgorithm key = (ICspAsymmetricAlgorithm)cert.PrivateKey;
const int PVK_TYPE_KEYCONTAINER = 2;
if (key == null)
{
return IntPtr.Zero;
}
SIGNER_PROVIDER_INFO providerInfo = new SIGNER_PROVIDER_INFO
{
cbSize = (uint)Marshal.SizeOf(typeof(SIGNER_PROVIDER_INFO)),
pwszProviderName = Marshal.StringToHGlobalUni(key.CspKeyContainerInfo.ProviderName),
dwProviderType = (uint)key.CspKeyContainerInfo.ProviderType,
dwPvkChoice = PVK_TYPE_KEYCONTAINER,
Union1 = new SIGNER_PROVIDER_INFO.SignerProviderUnion
{
pwszKeyContainer = Marshal.StringToHGlobalUni(key.CspKeyContainerInfo.KeyContainerName)
},
};
IntPtr pProviderInfo = Marshal.AllocHGlobal(Marshal.SizeOf(providerInfo));
Marshal.StructureToPtr(providerInfo, pProviderInfo, false);
return pProviderInfo;
}
// Use SignerSign
private static void SignCode(IntPtr pSubjectInfo, IntPtr pSignerCert, IntPtr pSignatureInfo, IntPtr pProviderInfo)
{
int hResult = SignerSign(
pSubjectInfo,
pSignerCert,
pSignatureInfo,
pProviderInfo,
null,
IntPtr.Zero,
IntPtr.Zero
);
if (hResult != 0)
{
// See if we can get anything useful. Jury's still out on this one.
Marshal.ThrowExceptionForHR(Marshal.GetHRForLastWin32Error());
}
}
// Use SignerSignEx
private static void SignCode(uint dwFlags, IntPtr pSubjectInfo, IntPtr pSignerCert, IntPtr pSignatureInfo, IntPtr pProviderInfo, out SIGNER_CONTEXT signerContext)
{
int hResult = SignerSignEx(
dwFlags,
pSubjectInfo,
pSignerCert,
pSignatureInfo,
pProviderInfo,
null,
IntPtr.Zero,
IntPtr.Zero,
out signerContext
);
if (hResult != 0)
{
// See if we can get anything useful. Jury's still out on this one.
Marshal.ThrowExceptionForHR(Marshal.GetHRForLastWin32Error());
}
}
// Use SignerTimeStamp
private static void TimeStampSignedCode(IntPtr pSubjectInfo, string timestampUrl)
{
int hResult = SignerTimeStamp(
pSubjectInfo,
timestampUrl,
IntPtr.Zero,
IntPtr.Zero
);
if (hResult != 0)
{
// We can't get anything useful from GetHRForLastWin32Error, so let's throw our own.
//Marshal.ThrowExceptionForHR(Marshal.GetHRForLastWin32Error());
throw new Exception(string.Format(@"""{0}"" could not be used at this time. If necessary, check the timestampUrl, internet connection, and try again.", timestampUrl));
}
}
// Use SignerTimeStampEx
private static void TimeStampSignedCode(uint dwFlags, IntPtr pSubjectInfo, string timestampUrl, out SIGNER_CONTEXT signerContext)
{
int hResult = SignerTimeStampEx(
dwFlags,
pSubjectInfo,
timestampUrl,
IntPtr.Zero,
IntPtr.Zero,
out signerContext
);
if (hResult != 0)
{
// We can't get anything useful from GetHRForLastWin32Error, so let's throw our own.
//Marshal.ThrowExceptionForHR(Marshal.GetHRForLastWin32Error());
throw new Exception(string.Format(@"""{0}"" could not be used at this time. If necessary, check the timestampUrl, internet connection, and try again.", timestampUrl));
}
}
#endregion
}
}
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