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The Security library in VisualWorks went through sweeping changes recently. Main change is replacing native smalltalk implementations of various cryptographic algorithms with pluggable interfaces to external libraries, but also a complete rewrite of the SSL implementation to support all current versions of the protocol (SSL3.0 & TLS 1.0, 1.1 and 1.2). Introducing dependencies on external libraries can complicate deployment, however the resulting pluggability of implementation and perfomance boost we're getting in exchange should more then pay off in terms of widening the scope of potential applications, where the purely native implementation was simply not acceptable. In this talk we will survey these changes and discuss their impact and backward compatibility implications.