I tried that, with no success.
Also compiled 5.51 from source with the same result.
I get this:

sendto in send_ip_packet_sd: sendto(4, packet, 60, 0, ya.da.ya.da, 16) => No route to host Offending packet: TCP ya.da.ya.da:59268 > ya.da.ya.da:80 ttl=55 id=27672 iplen=60 seq=3496514045 win=128 <wscale 10,nop,mss 265,timestamp 4294967295 0,sackOK>

I went on to clean up like nobodys business, ie

# pfctl -s rules
pass all no state
pass all user = 0 no state (i know)

Still doesn't work.

Just to be sure I tried disabling pf, and ofcourse that does the trick.
But as I said, thats not an option for me.

Any more suggestions? Is pf configurable on a lower level outside the ruleset?

Is there a way, good or bad, to relax pf enough to let nmap do its
OS detection?
I am on 4.8.

You can always disable pf (pfctl -d). I'd also expect any sensible
configuration without "scrub" or (implicit) "keep state" to work, but I
didn't check that.

E.g. you could try

set skip on lo0
pass
block in on ! lo0 proto tcp to port 6000:6010
pass user root no state
pass icmp no state

                Joachim

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