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* ConTeXt MKIV will never be up-to-date and will hardly ever be hot-fixed.
* MikTeX only updates binaries every now and then. Since ConTeXt MKIV strongly depends on LuaTeX version, ConTeXt cannot be updated arbitrarily and the updates may become out-of-sync with currently included LuaTeX version. If that happens, ConTeXt stops working.
* MikTeX now ships for two architectures: 32-bit and 64-bit. If LuaTeX gets out-of-sync on those two, ConTeXt will necessary be broken on at least on one of them.
* Hans likes to reimplement every bit and piece of standard TeX installations (like kpathsea, texmf.cnf, ...). This has two major consequences:
** Author of MikTeX may not always be aware of modifications and might implement requirements for these features with delay. In the meantime ConTeXt might become broken.
** Download of packages on request doesn't work with ConTeXt MKIV. The feature is hooked into kpathsea, ConTeXt doesn't use kpathsea, but doesn't provide any alternative for this either.
* For all of the reasons already mentioned, the number of ConTeXt users on MikTeX is very small which means less testing and more problems.
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