This approach works fine for us (iTextSharp 5.3.3). We use smart-card and USB-token (vendor – www.author.kiev.ua): X509Store store = new X509Store(StoreLocation.CurrentUser); store.Open(OpenFlags.ReadOnly); X509Certificate2Collection sel = X509Certificate2UI.SelectFromCollection(store.Certificates, null, null, X509SelectionFlag.SingleSelection); X509Certificate2 cert = sel[0]; Org.BouncyCastle.X509.X509CertificateParser cp = new Org.BouncyCastle.X509.X509CertificateParser(); Org.BouncyCastle.X509.X509Certificate[] chain = new Org.BouncyCastle.X509.X509Certificate[] { cp.ReadCertificate(cert.RawData)}; IExternalSignature externalSignature = new X509Certificate2Signature(cert, “SHA-1”); PdfReader pdfReader = new … Read more