Replicating what Stunnel does but with caddy-l4

Sorry, I misunderstood. You can do that as well, but you’ll have to run an instance of caddy-l4 on the Windows machine as a proxy server to your upstream. Here’s working config:

{
	"apps": {
		"layer4": {
			"servers": {
				"ssh-proxy": {
					"listen": ["127.0.0.1:8443"],
					"routes": [
						{
							"handle": [
								{
									"handler": "proxy",
									"upstreams": [
										{
											"dial": ["example.com:443"],
											"tls": {
												"server_name": "example.com"
											}
										}
									]
								}
							]
						}
					]
				}
			}
		}
	}
}

You can then run ssh -p 8443 username@localhost, and it’ll wrap the connection in TLS to upstream, which is then unwrapped into ssh again.

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