Can't SSH for 5 minutes+ after boot up

Solution 1:

My friend, I suggest that we examine the routing table in a 'before / after' manner: before the problem occurs; after the problem has occurred.

Could you kindly post the output of the following before and after the behavior occurs:

sudo netstat -nr 

I assume from looking at the ssh debug you posted that you are ssh'ing to the ip address, and not a hostname. Is this correct? If not, then we should look at the domain name resolution.

sudo scutil --dns

as well as

sudo cat /etc/resolv.conf

would help in this case.

Lastly, let's rule out any egress filtering on the firewall. It is a lot of information, but better that we have the full perspective, from rules to NAT to timeouts and states:

sudo pfctl -vvv -sa

F.