diff --git a/acme/simple_http_challenge.go b/acme/simple_http_challenge.go
index a74bf744..16ad35eb 100644
--- a/acme/simple_http_challenge.go
+++ b/acme/simple_http_challenge.go
@@ -97,8 +97,10 @@ loop:
 		case "pending":
 			break
 		case "invalid":
+			listener.Close()
 			return errors.New("The server could not validate our request.")
 		default:
+			listener.Close()
 			return errors.New("The server returned an unexpected state.")
 		}
 
diff --git a/acme/simple_http_challenge_test.go b/acme/simple_http_challenge_test.go
index 5d2e8332..36a76536 100644
--- a/acme/simple_http_challenge_test.go
+++ b/acme/simple_http_challenge_test.go
@@ -1,10 +1,15 @@
 package acme
 
 import (
+	"crypto/tls"
+	"encoding/json"
 	"io/ioutil"
 	"net/http"
+	"net/http/httptest"
 	"strings"
 	"testing"
+
+	"github.com/square/go-jose"
 )
 
 func TestSimpleHTTPCanSolve(t *testing.T) {
@@ -31,3 +36,89 @@ func TestSimpleHTTPCanSolve(t *testing.T) {
 		t.Errorf("Expected CanSolve to return %t for domain 'localhost' but was %t", expected, actual)
 	}
 }
+
+func TestSimpleHTTP(t *testing.T) {
+	privKey, err := generatePrivateKey(512)
+	if err != nil {
+		t.Errorf("Could not generate public key -> %v", err)
+	}
+	jws := &jws{privKey: privKey}
+
+	ts := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+	}))
+
+	solver := &simpleHTTPChallenge{jws: jws}
+	clientChallenge := challenge{Type: "simpleHttps", Status: "pending", URI: ts.URL, Token: "123456789"}
+
+	// validate error on non-root bind to 443
+	if err = solver.Solve(clientChallenge, "test.domain"); err == nil {
+		t.Error("BIND: Expected Solve to return an error but the error was nil.")
+	}
+
+	// Validate error on unexpected state
+	solver.optPort = "8080"
+	if err = solver.Solve(clientChallenge, "test.domain"); err == nil {
+		t.Error("UNEXPECTED: Expected Solve to return an error but the error was nil.")
+	}
+
+	// Validate error on invalid status
+	ts.Config.Handler = http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		failed := challenge{Type: "simpleHttps", Status: "invalid", URI: ts.URL, Token: "123456789"}
+		jsonBytes, _ := json.Marshal(&failed)
+		w.Write(jsonBytes)
+	})
+	if err = solver.Solve(clientChallenge, "test.domain"); err == nil {
+		t.Error("FAILED: Expected Solve to return an error but the error was nil.")
+	}
+
+	// Validate no error on valid response
+	ts.Config.Handler = http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		valid := challenge{Type: "simpleHttps", Status: "valid", URI: ts.URL, Token: "123456789"}
+		jsonBytes, _ := json.Marshal(&valid)
+		w.Write(jsonBytes)
+	})
+	if err = solver.Solve(clientChallenge, "test.domain"); err != nil {
+		t.Errorf("VALID: Expected Solve to return no error but the error was -> %v", err)
+	}
+
+	// Validate server on port 8080 which responds appropriately
+	ts.Config.Handler = http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		var request challenge
+
+		clientJws, _ := ioutil.ReadAll(r.Body)
+		j, err := jose.ParseSigned(string(clientJws))
+		if err != nil {
+			t.Errorf("Client sent invalid JWS to the server. -> %v", err)
+		}
+		output, err := j.Verify(&privKey.PublicKey)
+		if err != nil {
+			t.Errorf("Unable to verify client data -> %v", err)
+		}
+		json.Unmarshal(output, &request)
+
+		transport := &http.Transport{TLSClientConfig: &tls.Config{InsecureSkipVerify: true}}
+		client := &http.Client{Transport: transport}
+
+		reqURL := "https://localhost:8080/.well-known/acme-challenge/" + request.Path
+		t.Logf("Request URL is: %s", reqURL)
+		req, _ := http.NewRequest("GET", reqURL, nil)
+		req.Host = "test.domain"
+		resp, err := client.Do(req)
+		if err != nil {
+			t.Errorf("Expected the solver to listen on port 8080 -> %v", err)
+		}
+
+		body, _ := ioutil.ReadAll(resp.Body)
+		bodyStr := string(body)
+		if bodyStr != "123456789" {
+			t.Errorf("Expected the solver to return the token %s but instead returned '%s'", "123456789", bodyStr)
+		}
+
+		valid := challenge{Type: "simpleHttps", Status: "valid", URI: ts.URL, Token: "123456789"}
+		jsonBytes, _ := json.Marshal(&valid)
+		w.Write(jsonBytes)
+	})
+	if err = solver.Solve(clientChallenge, "test.domain"); err != nil {
+		t.Errorf("VALID: Expected Solve to return no error but the error was -> %v", err)
+	}
+}