One could create a license, the MSFT_LEGAL_CORNER_CASE license, that is in no way "open-source" simply because it requires nothing with respect to source code, but that is anti-tivo in requiring that anyone distributing a signed copy of the binary it must distribute the private key.
It wouldn't be on any of their blacklists because its completely made-up, presumably it must be covered under some generic clause in the contract, and that neither uploading a file now downloading a binary will oblige MSFT... But why make such a fuss over the GPLv3 and disallowed licenses when you can't cover the actual item of concern with those clauses.
A much simpler solution is obvious. Don't return the binary. You upload the binary, they send you back a signature with a placeholder (all 00 or EE) for your binary, you insert the binary into the signature packet. No need for them to dirty their hands by distributing your binary.
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