File file = new File("test.pdf");
        byte[] fileContent = FileUtils.readFileToByteArray(file);
        
        Advapi32 lib = Native.loadLibrary("advapi32", Advapi32.class);
        Advapi32Wrapper advapi32 = new Advapi32Wrapper(lib);
        // провайдер, алиас контейнера, пароль
        X509Certificate cert = advapi32.getCentificate("CRYPTOPROCSP", "alias", "password");
        
        final byte[] hash = advapi32.CryptSignHashA(fileContent);
        
        List<X509Certificate> certList = new ArrayList<>();
        CMSTypedData msg = new CMSProcessableFile(file);
        certList.add(cert);
        
        Store<?> certs = new JcaCertStore(certList);
        CMSSignedDataGenerator gen = new CMSSignedDataGenerator();
        ContentSigner signer = new ContentSigner() {
            @Override
            public AlgorithmIdentifier getAlgorithmIdentifier() {
                return new AlgorithmIdentifier(new ASN1ObjectIdentifier(cert.getSigAlgOID()));
            }
            
            @Override
            public OutputStream getOutputStream() {
                return new ByteArrayOutputStream();
            }
            
            @Override
            public byte[] getSignature() {
                return hash;
            }
        };
    
        JcaDigestCalculatorProviderBuilder dcpb = new JcaDigestCalculatorProviderBuilder();
        JcaSignerInfoGeneratorBuilder sigb = new JcaSignerInfoGeneratorBuilder(dcpb.build());
        
        boolean hasNoSignedAttributes = true;
        sigb.setDirectSignature(hasNoSignedAttributes);
        
        SignerInfoGenerator g = sigb.build(signer, cert);
        gen.addSignerInfoGenerator(g);
        gen.addCertificates(certs);
        CMSSignedData sigData = gen.generate(msg, false);
        byte[] sig = sigData.getEncoded();