I will take a stab at it, but I am not going to be able to cover it all here !

A .NET port of OpenSSL would require replacing the C style DLL interface with a .NET 
Object DLL.  The OpenSSL source code would have to be able to be compiled under the C# 
(pronounced c sharp) compiler.  Microsoft has just released Visual Studio 7.0.  
Version 7.0 produces .NET dll's. exe's, etc.  The new framework that is required to 
execute a .NET component (dll or exe) is called the common language runtime (CLR).  A 
.NET component gets just in time compiled (JIT) when it is needed and optimized for 
the operating system and hardware it is running under.  When future 64 bit versions of 
Windows arrive, .NET components will already be 64 bit when run under the new 
operating system.

The C# language is NOT a superset of the C or C++ languages.  Porting OpenSSL would be 
a real job!

I believe that most future software development is and will be done as a .NET 
component and that if OpenSSL is not ported to it, then OpenSSL will die the same fate 
as Windows 3.1 
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