Thank you for using our services. In the ideal case you'd make sure that you keep a backup of your custom module project on the development environment, as otherwise this ould make further modifications/extending etc impossible. If you have the module source, as you properly pointed outt he approach is pretty much straightforward - replace the referenced Telerik assemblies with the newer ones, point the csproj file to the correct version of the enhancer and build the module.
However, if you have the module dll only, then you should be able to use bindingRedirect element in the web.config to point it to the newer version of the Telerik assemblies, there should be no need for rebuilding and enhancing the project (please note that you deployed module dlls should be already enhanced). The only drawback in that scenario is that if any breaking changes have been introduced in the latter version they won't be reflected in the module, however between versions 4.4 and 5.0 I cannot recall any that would affect that particular functionality.
Please do not hesitate to get back to me if any issues persist.
All the best,
the Telerik team
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