IIS8.5 Integrated Windows Authentication

I am trying to use Caddy in front of an ASP.NET website hosted on IIS8.5 that uses Integrated Windows Authentication but am presented with an authentication challenge repeatedly even when entering correct details.

Some searches suggested the problem with http2 so I have tried executing Caddy with -http2=false and setting alpn http/1.1 in the tls directive but the result is the same, it just keeps asking me to log in.

The site works fine when hit directly. I am not using TLS on either the actual site or within Caddy as this is only a test before I implement properly and this is the first problem I’ve found with it.

How can I get integrated authentication working through Caddy?

Some quick research indicates that NTLM sends other TCP packets alongside the HTTP connection. I’m sorry, I’m not familiar enough with the protocol to say how Nginx and Apache achieve it - there are several accounts that they work with some keepalive settings tweaking - but you could try with a TCP proxy instead and see if that works. (Caddy with the net server type option could provide that function)

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