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Re:Infrastructure Security Without Slowing Down Developers by old-gregg on Friday May 08, 2020 @04:50PM (#23119302)
The proxy does not authenticate users. When a user shows up without a certificate, a proxy simply redirects to an OAuth2 / SAML endpoint such as Github or Google. When OAuth redirect comes back, the proxy forwards user's identity to the certificate authority (usual SSO flow), which issues an SSH certificate which gets sent back to the client.

Now, "armed" with a certificate, the client can try again, in which case the proxy simply forwards the request to the destination host, which verifies the certificate. It is the same as having a non-terminating HTTP/TLS proxy/load balancer, just for SSH.

Re:Infrastructure Security Without Slowing Down Developers by p4l4g4 on Sunday May 10, 2020 @10:29AM (#23132835)
Ah, interesting! Thanks for your response. What do you use to get this work flow going? Would be really interested in the underlying infra. Do you have any pointers to get me deeper in this subject?
Re:Infrastructure Security Without Slowing Down Developers by old-gregg on Tuesday May 12, 2020 @07:11PM (#23161241)
The entire thing is on Github: https://github.com/gravitational/teleport

Quickstart: https://gravitational.com/teleport/docs/quickstart/

To quickly answer your question: if you rename teleport client "tsh" to "ssh", trying to use it without a certificate will trigger SSO workflow. The alternative is to issue "tsh login" CLI command in the morning.