diff --git a/cmd/integration_test.go b/cmd/integration_test.go
index 96771e96..ed1320cb 100644
--- a/cmd/integration_test.go
+++ b/cmd/integration_test.go
@@ -441,7 +441,7 @@ func validateProxyResponseWithUpstream(t *testing.T, test *TestCase, resp *http.
 	t.Logf("HTTP Response: %#v", resp)
 
 	if test.OverConnect {
-		a.Contains(err.Error(), "Failed to connect to remote host")
+		a.Contains(err.Error(), "Failed to resolve remote hostname")
 	} else {
 		a.Equal(http.StatusBadGateway, resp.StatusCode)
 	}
diff --git a/pkg/smokescreen/smokescreen.go b/pkg/smokescreen/smokescreen.go
index 2c3c61d4..69e9dd38 100644
--- a/pkg/smokescreen/smokescreen.go
+++ b/pkg/smokescreen/smokescreen.go
@@ -356,6 +356,11 @@ func rejectResponse(pctx *goproxy.ProxyCtx, err error) *http.Response {
 			status = "Gateway timeout"
 			code = http.StatusGatewayTimeout
 			msg = "Timed out connecting to remote host: " + e.Error()
+
+		} else if e, ok := err.(*net.DNSError); ok {
+			status = "Bad gateway"
+			code = http.StatusBadGateway
+			msg = "Failed to resolve remote hostname: " + e.Error()
 		} else {
 			status = "Bad gateway"
 			code = http.StatusBadGateway
@@ -620,9 +625,13 @@ func handleConnect(config *Config, pctx *goproxy.ProxyCtx) (string, error) {
 		pctx.Error = denyError{err}
 		return "", pctx.Error
 	}
+
+	// checkIfRequestShouldBeProxied can return an error if either the resolved address is disallowed,
+	// or if there is a DNS resolution failure.
 	sctx.decision, sctx.lookupTime, pctx.Error = checkIfRequestShouldBeProxied(config, pctx.Req, destination)
 	if pctx.Error != nil {
-		return "", denyError{pctx.Error}
+		// DNS resolution failure
+		return "", pctx.Error
 	}
 	if !sctx.decision.allow {
 		return "", denyError{errors.New(sctx.decision.reason)}
diff --git a/pkg/smokescreen/smokescreen_test.go b/pkg/smokescreen/smokescreen_test.go
index 4e653407..4e01ef9a 100644
--- a/pkg/smokescreen/smokescreen_test.go
+++ b/pkg/smokescreen/smokescreen_test.go
@@ -406,11 +406,10 @@ func TestHealthcheck(t *testing.T) {
 
 var invalidHostCases = []struct {
 	scheme    string
-	expectErr bool
 	proxyType string
 }{
-	{"http", false, "http"},
-	{"https", true, "connect"},
+	{"http", "http"},
+	{"https", "connect"},
 }
 
 func TestInvalidHost(t *testing.T) {
@@ -430,12 +429,19 @@ func TestInvalidHost(t *testing.T) {
 			client, err := proxyClient(proxySrv.URL)
 			r.NoError(err)
 
+			// This hostname does not exist and should never resolve
 			resp, err := client.Get(fmt.Sprintf("%s://notarealhost.test", testCase.scheme))
-			if testCase.expectErr {
-				r.Contains(err.Error(), "Request rejected by proxy")
+			if testCase.scheme == "https" {
+				r.Error(err)
+				r.Contains(err.Error(), "Bad gateway")
 			} else {
+				// Plain HTTP
 				r.NoError(err)
 				r.Equal(http.StatusBadGateway, resp.StatusCode)
+
+				defer resp.Body.Close()
+				b, _ := ioutil.ReadAll(resp.Body)
+				r.Contains(string(b), "Failed to resolve remote hostname")
 			}
 
 			entry := findCanonicalProxyDecision(logHook.AllEntries())