MacOS – MacBook on takes long to establish WiFi connection

Update: It wasn't the VPN client causing this, but after lengthy troubleshooting (see comments) it turned out to be Skype, possibly due to UPnP related bugs.

Try disabling your Cisco AnyConnect(?) VPN client (if you're not sure how, open Activity Monitor, find a process named acvpnagent and quit it).

From your description, it may well be the case that the VPN client is either failing to establish a tunnel or taking a rather long to do so, either of which could cause the apparent loss of the default route you're describing (you can ping anything on your local network, but nothing past the router).

If disabling the above (and any other) VPN client doesn't resolve it, please add the results of:

• ifconfig (not just ifconfig en1 - there's an interface utun0 appearing in your log)
• netstat -rnfinet

... at each of these stages:

• immediately after connecting to your Wifi (while the network seems to be up)
• during the problem
• and after recovery

This is indeed quite broken in Mountain Lion. Once you've fixed up the default route as you describe in the question, you're still left with the problem that Mountain Lion is giving its bridge interface address to clients as both the router address (which is correct) and as the DNS server address (which isn't).

Verify that this is the problem by entering an HTTP server IP address into the address bar on a client web browser when connected through your Mac after you fix default routes, and it should load up fine.

My solution to this problem is to fix up the route as you describe -- which could be automated, of course -- and to keep BIND (aka /usr/sbin/named) running in the background on my Mac in a forward-only configuration, forwarding all queries to Google's public DNS servers. This doesn't fix the underlying brokenness in Mountain Lion, but it makes things start working for the clients.

A couple useful resources:

http://www.macshadows.com/kb/index.php?title=How_To:_Enable_BIND_-_Mac_OS_X%27s_Built-in_DNS_Server (how to fire up BIND on OS X)

http://gleamynode.net/articles/2267/ (how to configure BIND for forward-only operation -- of course you will not want to make BIND only listen on 127.0.0.1)

It would be far preferable for Apple to make this feature of their OS work as advertised, but in the meantime I've found this is a viable workaround.