Windows – Simple DNS Server or Tool for Local Web App Development

Refer to the DNSmasq documentation, especially the dnsmasq manpage and sample configuration file. The local keyword tells DNSmasq to perform those domain lookups with local data. This affects requests send to DNSmasq for foo.localnet and bar.localnet, for example. I don't think this is what you want.

# Add local-only domains here, queries in these domains are answered
# from /etc/hosts or DHCP only.
local=/localnet/

To force host/subdomain lookups to resolve to a specific address, you'd probably want to use the address keyword. The second example below should allow web1.devbox and web2.devbox and web73872.devbox to all resolve to the address specified.

# Add domains which you want to force to an IP address here.
# The example below send any host in doubleclick.net to a local
# webserver.
address=/doubleclick.net/127.0.0.1

# for your example
address=/devbox/192.168.3.99

I use DNSmasq at home to handle simple DNS stuff for my LAN; in that case, local and the associated domain and expand-hosts keywords are appropriate. The DNSmasq server is my primary nameserver, so all requests go through it; any nonlocal addresses are passed back to the ISP's nameserver. You might consider that configuration if possible.

sorry for the delay, I finally found a solution after lots of experiments. First of all, here's the zone file I use for the local. domain:

$TTL 1800

@       IN      SOA     local. root.porto.local. (
                        2010061500      ; serial
                        7200            ; refresh
                        3600            ; retry
                        604800          ; expire
                        1800            ; default_ttl
)

                NS      porto.local.

$ORIGIN local.

porto   IN      A       192.168.1.32
www             IN      A       192.168.1.32

to which I can add lines like

www.example.com IN      A       192.168.1.32

which results in the ability to query for www.example.com.local, and that's one thing.

In order to take into account of Drupal's weird behaviour, I actually found a solution that doesn't prevent me from working with the real remote www.example.com while working on a local copy, except that I had to set a zone for local.www.example.com and the host line for www which results in the odd and long www.local.www.example.com... frankly a bit too much to keep my mental health. I'll go for the local. way and s/.local// the database dump I'm going to deploy to the production server.

Thanks to everyone that replied.