Pivotal Engineering Journal

Technical articles from Pivotal engineers.

Troubleshooting Obscure OpenSSH Failures

How an elusive CI (Continuous Integration) error led us to uncover a hidden man-in-the-middle ssh proxy.

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Categories:   Networking   
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By using tcpdump to troubleshoot an elusive error, we uncovered a man-in-the-middle (MITM) ssh proxy installed by our information security (InfoSec) team to harden/protect a set of machines which were accessible from the internet. The ssh proxy in question was Palo Alto Network’s (PAN) Layer 7 (i.e. it worked on any port, not solely ssh’s port 22) proxy, and was discovered when we observed a failure to negotiate ciphers during the ssh key exchange.

The Problem

In our team’s Concourse CI pipelines, we create new PCF Pivotal Cloud Foundry environments, subject them to a rigorous battery of tests, and then destroy them. Among our tests is the Container Networking Acceptance test suite (NATS or CNATS—not to be confused with the NATS messaging bus), which runs many cf ssh commands to test app-to-app connectivity.

The error was elusive, but inconvenient — it would cause an entire test suite to fail. Our only clue was a cryptic ssh failure:

Error opening SSH connection: ssh: handshake failed: EOF

Let’s be clear: we’re not using OpenSSH in our tests. Sure, we’re using the SSH protocol as implemented by the Golang library, but we’re not using the command line tool which so many of us know and love. In other words, we type cf ssh instead of ssh.

The purpose of this specialized implementation of the OpenSSH protocol is to allow users of our Pivotal Application Service (PAS) software to connect to their application, typically to debug.

Once again, though, it’s not quite OpenSSH. For one thing, our server-side binds to port 2222, not sshd’s 22. Also, it’s written in Golang, not C (both the client and the server).

Defining the problem

The problem wasn’t consistent. In fact, over the course of a 20-minute test run, it would only appear once.

It didn’t appear everywhere—one of our environments, maintained in San Francisco, seemed immune to the problem. In fact, the problem reared its ugly head only in our San Jose environments.

And, strangest of all, the problem only occurred on the first connection attempt. The first time cf ssh was run, it would fail, but subsequent attempts succeeded.

We attempted connecting from workstations in Palo Alto, San Francisco, and Santa Monica. The behavior remained consistent: the first attempt would fail, and the remaining would succeed.

We tried using ssh as a client instead of cf ssh. Same behavior: first would fail, remainder succeed.

We tried bringing up sshd as a server. The results surprised us: no failures. Not one. Our ssh-proxy failed, but sshd didn’t — what was going on?

We knew it was time for tcpdump. If we were going to get any further, we needed to examine the raw packets.

Using tcpdump on our Server

We ran tcpdump on our server (the “Diego Brain”) to determine what was happening during failed cf ssh connections. We discovered that, from the Diego Brain’s perspective, the user was shutting down the connection (by sending a FIN packet).

From the standpoint of the Diego brain (, the user ( terminates (FIN) the session immediately after key exchange negotiation

From the standpoint of the Diego brain (, the user ( terminates (FIN) the session immediately after key exchange negotiation

We dug deeper — was there anything happening in the key exchange that caused the connection to shut down?

Yes, there was something happening: the client and the Diego Brain could not agree on a common set of ciphers.

These were the ciphers offered by the Diego Brain. Note that these ciphers are the ones included in Golang’s ssh package:

  • “curve25519-sha256@libssh.org”
  • “ecdh-sha2-nistp256”
  • “ecdh-sha2-nistp384”
  • “ecdh-sha2-nistp521”
  • “diffie-hellman-group14-sha1”
  • “diffie-hellman-group1-sha1”

These were the ciphers offered by the client:

  • “diffie-hellman-group-exchange-sha256”
  • “diffie-hellman-group-exchange-sha1”

We believe that the client shut down the connection because it could not agree on a common cipher for key exchange. But the client and server were both written in Golang, so their cipher suites should be identical. In fact, both Diffie Hellman group exchange ciphers are explicitly considered to be legacy protocols by the Golang maintainers. Why was the client’s cipher suite different, and why did it include legacy protocols?

At this point we also noticed that the SSH protocol was unexpected: it was SSH-2.0-PaloAltoNetworks_0.2. We decided to trace the packets from the client.

Using tcpdump on our Client

We ran tcpdump on our client, and attempted to connect (via ssh, not our custom client, not cf ssh) to our Diego Brain. We found the unexpected SSH protocol again, SSH-2.0-PaloAltoNetworks_0.2, but this time it was our Diego Brain presenting it:

A packet trace of an two attempted connections to port 2222; the first failed, and the second succeeded.

A packet trace of an two attempted connections to port 2222; the first failed, and the second succeeded.

But the SSH protocol SSH-2.0-PaloAltoNetworks_0.2 was only presented when the connection subsequently failed. In the diagram above, we can see that the ostensible Diego Brain shut down the connection by sending a FIN packet (packet 19) to our client.

IOPS to the Rescue

We contacted IOPS, the Pivotal organization which maintains the network, who explained that the firewall is configured to intercept and proxy all ssh connections originating from or terminating at the San Jose datacenter in order to prevent ssh tunnel attacks, since the San Jose environments are accessible from the internet.

Our Conclusions

Our networking model was wrong:

Unbeknownst to us, the Palo Alto Networks firewall was intercepting our ssh traffic.

Unbeknownst to us, the Palo Alto Networks firewall was intercepting our ssh traffic.

We concluded that our cf ssh connection actually works this way:

  • Our firewall attempts to proxy all ssh connections to San Jose.
  • When it attempts to contact the backend, it realizes it doesn’t have a common cipher suite for key exchange, and can’t establish a connection
  • When it can’t establish a connection with the server, it sends a FIN to the client (EOF)
  • It proceeds to whitelist the client-IP, server-IP, server-port tuple for a period of time (we think 15-20 minutes). It does not attempt to proxy during that time
  • It will attempt to proxy new client connections from different IP addresses during that time

Our final resolution to this issue was a workaround wherein each test suite that runs cf ssh, we “prime the pump” by running a cf ssh command, which we expect to fail, before running the test suite.