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any idea why Wireshark doesn't handle this on it's own?
Probably because Apple, in their infinite perversity, changed something, so that there's another step in the "turn monitor mode on" dance that Wireless Diagnostics is performing but libpcap (which is what both tcpdump and Wireshark rely on to turn monitor mode on) isn't performing, or so that there's some extra entitlement, which Apple gave to Wireless Diagnostics, required to turn on monitor mode.
This works without a hitch on my older MacBook Pro running an older OS version....
It might be an issue with drivers for newer Wi-Fi adapters.
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