Trying to ssh out, via Squid, to a Digital Ocean droplet. Notice Squid is running locally on :80, and SSH on the droplet is :22

gistfile1.txt

➜  ssh 107.170.89.168 -vvv                 
OpenSSH_6.2p2 Ubuntu-6ubuntu0.2, OpenSSL 1.0.1e 11 Feb 2013
debug1: Reading configuration data /home/phil/.ssh/config
debug1: /home/phil/.ssh/config line 1: Applying options for *
debug1: Reading configuration data /etc/ssh/ssh_config
debug1: /etc/ssh/ssh_config line 19: Applying options for *
debug2: ssh_connect: needpriv 0
debug1: Executing proxy command: exec corkscrew 127.0.0.1 80 107.170.89.168 22
debug1: permanently_drop_suid: 1000
debug3: Incorrect RSA1 identifier
debug3: Could not load "/home/phil/.ssh/id_rsa" as a RSA1 public key
debug1: identity file /home/phil/.ssh/id_rsa type 1
debug1: Checking blacklist file /usr/share/ssh/blacklist.RSA-2048
debug1: Checking blacklist file /etc/ssh/blacklist.RSA-2048
debug1: identity file /home/phil/.ssh/id_rsa-cert type -1
debug1: identity file /home/phil/.ssh/id_dsa type -1
debug1: identity file /home/phil/.ssh/id_dsa-cert type -1
debug1: identity file /home/phil/.ssh/id_ecdsa type -1
debug1: identity file /home/phil/.ssh/id_ecdsa-cert type -1
debug1: Enabling compatibility mode for protocol 2.0
debug1: Local version string SSH-2.0-OpenSSH_6.2p2 Ubuntu-6ubuntu0.2
Proxy could not open connection to 107.170.89.168:  Service Unavailable
ssh_exchange_identification: Connection closed by remote host

➜   

Meanwhile, logs report 503, that droplet IP is not available.

==> /var/log/squid3/access.log <==
1396894845.680  59898 127.0.0.1 TCP_MISS/503 0 CONNECT 107.170.89.168:22 - HIER_NONE/- -
1396894879.680  60367 127.0.0.1 TCP_MISS/503 0 CONNECT 107.170.89.168:22 - HIER_NONE/- -
1396894895.585  60398 127.0.0.1 TCP_MISS/503 0 CONNECT 107.170.89.168:22 - HIER_NONE/- -