From owner-freebsd-security@FreeBSD.ORG  Wed Jun 16 19:01:53 2004
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To: Chuck Swiger <cswiger@mac.com>
From: Oliver Eikemeier <eikemeier@fillmore-labs.com>
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Subject: Re: nmap not scanning networks?
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Chuck Swiger wrote:

> Alex Povolotsky wrote:
>> Attempt to scan a network with any method except plain ping results in 
>> an error:
>> truss nmap -sT -p 21 '172.19.17.*'
>
> I can confirm the problem, anyway, although I'm not sure it's germane 
> to freebsd-security.  :-)
>
>> [...]
>> sendto(0x4,0x8094200,0,0x0,{ AF_INET 172.19.17.0:0 },0x10) ERR#49 
>> 'Can't assign requested address'
>> [...]
>> What's strange that man on send(2) doesn't state that EADDRNOTAVAIL 
>> can ever be returned from sendto().

Have you checked the firewall rules and routing tables on your machines?
Do you have the same problems with non-private IP ranges?

-Oliver