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Jitterbit provides an SDK to make creating custom plug-ins simple. The SDK provides for C++ incorporation into Jitterbit Source, Target or WS .If you are using C++ or Java, you can take advantage of classes that reduce the amount of code you need to write. The work to create a plug-in then is to act on a list of input files and data elements and provide a list of output files and data elements. If you are using another language -- and you can use any language capable of generating executable files on the platform you are using -- you can lobby in the Jitterbit forums for helper classes to be added in that language.
NOTE: Jitterbit Customers that are using their own custom Plug-ins are responsible for the security of the custom Plug-ins.