CryptSignMessageWithKey

// CRYPT32.dll
#include <windows.h>

BOOL CryptSignMessageWithKey(
    CRYPT_KEY_SIGN_MESSAGE_PARA* pSignPara,
    const BYTE* pbToBeSigned,
    DWORD cbToBeSigned,
    BYTE* pbSignedBlob,   // optional
    DWORD* pcbSignedBlob
);

<DllImport("CRYPT32.dll", SetLastError:=True, ExactSpelling:=True)>
Public Shared Function CryptSignMessageWithKey(
    pSignPara As IntPtr,   ' CRYPT_KEY_SIGN_MESSAGE_PARA*
    pbToBeSigned As IntPtr,   ' BYTE*
    cbToBeSigned As UInteger,   ' DWORD
    pbSignedBlob As IntPtr,   ' BYTE* optional, out
    ByRef pcbSignedBlob As UInteger   ' DWORD* in/out
) As Boolean
End Function

' pSignPara : CRYPT_KEY_SIGN_MESSAGE_PARA*
' pbToBeSigned : BYTE*
' cbToBeSigned : DWORD
' pbSignedBlob : BYTE* optional, out
' pcbSignedBlob : DWORD* in/out
Declare PtrSafe Function CryptSignMessageWithKey Lib "crypt32" ( _
    ByVal pSignPara As LongPtr, _
    ByVal pbToBeSigned As LongPtr, _
    ByVal cbToBeSigned As Long, _
    ByVal pbSignedBlob As LongPtr, _
    ByRef pcbSignedBlob As Long) As Long
' VBA7前提(PtrSafe)。32bit Office では LongPtr→Long。Integer=16bit / Long=32bit / LongLong=64bit。

import ctypes
from ctypes import wintypes

CryptSignMessageWithKey = ctypes.windll.crypt32.CryptSignMessageWithKey
CryptSignMessageWithKey.restype = wintypes.BOOL
CryptSignMessageWithKey.argtypes = [
    ctypes.c_void_p,  # pSignPara : CRYPT_KEY_SIGN_MESSAGE_PARA*
    ctypes.POINTER(ctypes.c_ubyte),  # pbToBeSigned : BYTE*
    wintypes.DWORD,  # cbToBeSigned : DWORD
    ctypes.POINTER(ctypes.c_ubyte),  # pbSignedBlob : BYTE* optional, out
    ctypes.POINTER(wintypes.DWORD),  # pcbSignedBlob : DWORD* in/out
]
# GetLastError: use ctypes.GetLastError() (or ctypes.WinDLL(use_last_error=True))

require 'fiddle'
require 'fiddle/import'

lib = Fiddle.dlopen('CRYPT32.dll')
CryptSignMessageWithKey = Fiddle::Function.new(
  lib['CryptSignMessageWithKey'],
  [
    Fiddle::TYPE_VOIDP,  # pSignPara : CRYPT_KEY_SIGN_MESSAGE_PARA*
    Fiddle::TYPE_VOIDP,  # pbToBeSigned : BYTE*
    -Fiddle::TYPE_INT,  # cbToBeSigned : DWORD
    Fiddle::TYPE_VOIDP,  # pbSignedBlob : BYTE* optional, out
    Fiddle::TYPE_VOIDP,  # pcbSignedBlob : DWORD* in/out
  ],
  Fiddle::TYPE_INT)

#[link(name = "crypt32")]
extern "system" {
    fn CryptSignMessageWithKey(
        pSignPara: *mut CRYPT_KEY_SIGN_MESSAGE_PARA,  // CRYPT_KEY_SIGN_MESSAGE_PARA*
        pbToBeSigned: *const u8,  // BYTE*
        cbToBeSigned: u32,  // DWORD
        pbSignedBlob: *mut u8,  // BYTE* optional, out
        pcbSignedBlob: *mut u32  // DWORD* in/out
    ) -> i32;
}
// crates: windows-sys provides ready-made bindings for this API.

$sig = @"
[return: MarshalAs(UnmanagedType.Bool)]
[DllImport("CRYPT32.dll", SetLastError = true)]
public static extern bool CryptSignMessageWithKey(IntPtr pSignPara, IntPtr pbToBeSigned, uint cbToBeSigned, IntPtr pbSignedBlob, ref uint pcbSignedBlob);
"@
$api = Add-Type -MemberDefinition $sig -Name 'CRYPT32_CryptSignMessageWithKey' -Namespace Win32 -PassThru
# $api::CryptSignMessageWithKey(pSignPara, pbToBeSigned, cbToBeSigned, pbSignedBlob, pcbSignedBlob)

#uselib "CRYPT32.dll"
#func global CryptSignMessageWithKey "CryptSignMessageWithKey" sptr, sptr, sptr, sptr, sptr
; CryptSignMessageWithKey varptr(pSignPara), varptr(pbToBeSigned), cbToBeSigned, varptr(pbSignedBlob), varptr(pcbSignedBlob)   ; 戻り値は stat
; pSignPara : CRYPT_KEY_SIGN_MESSAGE_PARA* -> "sptr"
; pbToBeSigned : BYTE* -> "sptr"
; cbToBeSigned : DWORD -> "sptr"
; pbSignedBlob : BYTE* optional, out -> "sptr"
; pcbSignedBlob : DWORD* in/out -> "sptr"
; ※HSP3.7は #func のため戻り値はシステム変数 stat に格納されます。

#uselib "CRYPT32.dll"
#cfunc global CryptSignMessageWithKey "CryptSignMessageWithKey" var, var, int, var, var
; res = CryptSignMessageWithKey(pSignPara, pbToBeSigned, cbToBeSigned, pbSignedBlob, pcbSignedBlob)
; pSignPara : CRYPT_KEY_SIGN_MESSAGE_PARA* -> "var"
; pbToBeSigned : BYTE* -> "var"
; cbToBeSigned : DWORD -> "int"
; pbSignedBlob : BYTE* optional, out -> "var"
; pcbSignedBlob : DWORD* in/out -> "var"
; ※出力/バッファ引数は var 方式(変数を直接渡す)。varptr 方式にも切替可。

; BOOL CryptSignMessageWithKey(CRYPT_KEY_SIGN_MESSAGE_PARA* pSignPara, BYTE* pbToBeSigned, DWORD cbToBeSigned, BYTE* pbSignedBlob, DWORD* pcbSignedBlob)
#uselib "CRYPT32.dll"
#cfunc global CryptSignMessageWithKey "CryptSignMessageWithKey" var, var, int, var, var
; res = CryptSignMessageWithKey(pSignPara, pbToBeSigned, cbToBeSigned, pbSignedBlob, pcbSignedBlob)
; pSignPara : CRYPT_KEY_SIGN_MESSAGE_PARA* -> "var"
; pbToBeSigned : BYTE* -> "var"
; cbToBeSigned : DWORD -> "int"
; pbSignedBlob : BYTE* optional, out -> "var"
; pcbSignedBlob : DWORD* in/out -> "var"
; ※出力/バッファ引数は var 方式(変数を直接渡す)。varptr 方式にも切替可。

import (
	"golang.org/x/sys/windows"
	"unsafe"
)

var (
	crypt32 = windows.NewLazySystemDLL("CRYPT32.dll")
	procCryptSignMessageWithKey = crypt32.NewProc("CryptSignMessageWithKey")
)

// pSignPara (CRYPT_KEY_SIGN_MESSAGE_PARA*), pbToBeSigned (BYTE*), cbToBeSigned (DWORD), pbSignedBlob (BYTE* optional, out), pcbSignedBlob (DWORD* in/out)
r1, _, err := procCryptSignMessageWithKey.Call(
	uintptr(pSignPara),
	uintptr(pbToBeSigned),
	uintptr(cbToBeSigned),
	uintptr(pbSignedBlob),
	uintptr(pcbSignedBlob),
)
_ = err  // syscall.Errno (valid when the call sets last-error)
_ = r1   // BOOL

function CryptSignMessageWithKey(
  pSignPara: Pointer;   // CRYPT_KEY_SIGN_MESSAGE_PARA*
  pbToBeSigned: Pointer;   // BYTE*
  cbToBeSigned: DWORD;   // DWORD
  pbSignedBlob: Pointer;   // BYTE* optional, out
  pcbSignedBlob: Pointer   // DWORD* in/out
): BOOL; stdcall;
  external 'CRYPT32.dll' name 'CryptSignMessageWithKey';

result := DllCall("CRYPT32\CryptSignMessageWithKey"
    , "Ptr", pSignPara   ; CRYPT_KEY_SIGN_MESSAGE_PARA*
    , "Ptr", pbToBeSigned   ; BYTE*
    , "UInt", cbToBeSigned   ; DWORD
    , "Ptr", pbSignedBlob   ; BYTE* optional, out
    , "Ptr", pcbSignedBlob   ; DWORD* in/out
    , "Int")   ; return: BOOL

●CryptSignMessageWithKey(pSignPara, pbToBeSigned, cbToBeSigned, pbSignedBlob, pcbSignedBlob) = DLL("CRYPT32.dll", "bool CryptSignMessageWithKey(void*, void*, dword, void*, void*)")
# 呼び出し: CryptSignMessageWithKey(pSignPara, pbToBeSigned, cbToBeSigned, pbSignedBlob, pcbSignedBlob)
# pSignPara : CRYPT_KEY_SIGN_MESSAGE_PARA* -> "void*"
# pbToBeSigned : BYTE* -> "void*"
# cbToBeSigned : DWORD -> "dword"
# pbSignedBlob : BYTE* optional, out -> "void*"
# pcbSignedBlob : DWORD* in/out -> "void*"
# なでしこ1は32bit・ANSI(Shift_JIS)。文字列=char*(ANSI)、ポインタ/ハンドル=void*(4byte)。