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copied!<p>I am running into a very similar problem trying to create a native C# tool for packing Chrome extensions (using SHA1, not MD5, but that's not a big difference). I believe I have tried literally every possible solution for .Net: System.Security.Cryptography, BouncyCastle, OpenSSL.Net and Chilkat RSA. </p> <p>The best solution is probably Chilkat; their interface is the cleanest and most straightforward, it's well-supported and well-documented, and there are a million examples. For instance, here's some code using their library that does something very close to what you want: <a href="http://www.example-code.com/csharp/rsa_signPkcs8.asp" rel="nofollow noreferrer">http://www.example-code.com/csharp/rsa_signPkcs8.asp</a>. However, it's not free (though $150 is not unreasonable, seeing as I have burned 2 days trying to figure this out, and I make a bit more than $75 a day!).</p> <p>As a free alternative, JavaScience offers up a number of crypto utilities in source form for multiple languages (including C#/.Net) at <a href="http://www.jensign.com/JavaScience/cryptoutils/index.html" rel="nofollow noreferrer">http://www.jensign.com/JavaScience/cryptoutils/index.html</a>. The one that's most salient to what you are trying to do is opensslkey (<a href="http://www.jensign.com/opensslkey/index.html" rel="nofollow noreferrer">http://www.jensign.com/opensslkey/index.html</a>), which will let you generate a RSACryptoServiceProvider from a .pem file. You can then use that provider to sign your code:</p> <pre><code> string pemContents = new StreamReader("pkcs8privatekey.pem").ReadToEnd(); var der = opensslkey.DecodePkcs8PrivateKey(pemContents); RSACryptoServiceProvider rsa = opensslkey.DecodePrivateKeyInfo(der); signature = rsa.SignData(data, new MD5CryptoServiceProvider()); </code></pre>

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