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Will Wireshark on Windows ever have working TLS/rpcaps support to match rpcapd deployments that do support TLS?

If either 1) somebody adds support for some native Windows TLS API to the socket code in sockutils.c (in addition to the existing OpenSSL/LibreSSL support), and that's picked up in a future version of Npcap, or 2) the Npcap people bundle an OpenSSL/LibreSSL library with Npcap, then, yes.