Stubbed out basic code to obtain Let's Encrypt cert

config/config.go

 package config
 
 import (
+	"crypto/rand"
+	"crypto/rsa"
+	"errors"
 	"fmt"
 	"io"
 	"log"
@@ -11,6 +14,7 @@ import (
 	"github.com/mholt/caddy/config/setup"
 	"github.com/mholt/caddy/middleware"
 	"github.com/mholt/caddy/server"
+	"github.com/xenolf/lego/acme"
 )
 
 const (
@@ -73,10 +77,60 @@ func Load(filename string, input io.Reader) (Group, error) {
 	// restore logging settings
 	log.SetFlags(flags)
 
+	privateKey, err := rsa.GenerateKey(rand.Reader, 2048)
+	if err != nil {
+		return Group{}, errors.New("Error Generating Key:" + err.Error())
+	}
+
+	for _, cfg := range configs {
+		// TODO: && hostname does not resolve to localhost (?) && TLS is not force-disabled
+		if !cfg.TLS.Enabled {
+			// Initiate Let's Encrypt
+			user := LetsEncryptUser{
+				Email: "example@mail.com",
+				Key:   privateKey,
+			}
+			client := acme.NewClient("http://192.168.99.100:4000", &user, 2048, "5001")
+			reg, err := client.Register()
+			if err != nil {
+				return Group{}, errors.New("Error Registering: " + err.Error())
+			}
+			user.Registration = reg
+
+			err = client.AgreeToTos()
+			if err != nil {
+				return Group{}, errors.New("Error Agreeing to ToS: " + err.Error())
+			}
+
+			certs, err := client.ObtainCertificates([]string{"caddy.dev"})
+			if err != nil {
+				return Group{}, errors.New("Error Obtaining Certs: " + err.Error())
+			}
+
+			fmt.Printf("%#v\n", certs)
+		}
+	}
+
 	// Group by address/virtualhosts
 	return arrangeBindings(configs)
 }
 
+type LetsEncryptUser struct {
+	Email        string
+	Registration *acme.RegistrationResource
+	Key          *rsa.PrivateKey
+}
+
+func (u LetsEncryptUser) GetEmail() string {
+	return u.Email
+}
+func (u LetsEncryptUser) GetRegistration() *acme.RegistrationResource {
+	return u.Registration
+}
+func (u LetsEncryptUser) GetPrivateKey() *rsa.PrivateKey {
+	return u.Key
+}
+
 // serverBlockToConfig makes a config for the server block
 // by executing the tokens that were parsed. The returned
 // config is shared among all hosts/addresses for the server