diff --git a/pkg/handler/handler_test.go b/pkg/handler/handler_test.go
index b87f9dd..fe700d0 100644
--- a/pkg/handler/handler_test.go
+++ b/pkg/handler/handler_test.go
@@ -692,7 +692,7 @@ func request(t *testing.T, client *http.Client, method, url string, headers ...h
 	assert.NoError(t, err)
 
 	for _, h := range headers {
-		req.Header.Set(h.key, h.value)
+		req.Header.Add(h.key, h.value)
 	}
 
 	resp, err := client.Do(req)
diff --git a/pkg/handler/reverseproxy.go b/pkg/handler/reverseproxy.go
index 442f1cb..43a89f0 100644
--- a/pkg/handler/reverseproxy.go
+++ b/pkg/handler/reverseproxy.go
@@ -152,6 +152,13 @@ func handleAutologin(src ReverseProxySource, w http.ResponseWriter, r *http.Requ
 	location := loginURL(target, "non-navigation request detected; responding with 401 and Location header")
 	w.Header().Set("Location", location)
 	w.WriteHeader(http.StatusUnauthorized)
+
+	if accepts(r, "*/*", "application/json") {
+		w.Header().Set("Content-Type", "application/json")
+		w.Write([]byte(`{"error": "unauthenticated, please log in"}`))
+	} else {
+		w.Write([]byte("unauthenticated, please log in"))
+	}
 }
 
 func isNavigationRequest(r *http.Request) bool {
@@ -168,10 +175,23 @@ func isNavigationRequest(r *http.Request) bool {
 	}
 
 	// fallback if browser doesn't support fetch metadata
-	acceptValues := strings.Split(r.Header.Get("Accept"), ",")
-	for _, v := range acceptValues {
-		if strings.ToLower(v) == "text/html" {
-			return true
+	return accepts(r, "text/html")
+}
+
+func accepts(r *http.Request, accepted ...string) bool {
+	// iterate over all Accept headers
+	for _, header := range r.Header.Values("Accept") {
+		// iterate over all comma-separated values in a single Accept header
+		for _, v := range strings.Split(header, ",") {
+			v = strings.ToLower(v)
+			v = strings.TrimSpace(v)
+			v = strings.Split(v, ";")[0]
+
+			for _, accept := range accepted {
+				if v == accept {
+					return true
+				}
+			}
 		}
 	}
 
diff --git a/pkg/handler/reverseproxy_test.go b/pkg/handler/reverseproxy_test.go
index f0a3a90..9fef9aa 100644
--- a/pkg/handler/reverseproxy_test.go
+++ b/pkg/handler/reverseproxy_test.go
@@ -37,7 +37,7 @@ func TestReverseProxy(t *testing.T) {
 	assertAutoLoginUnauthorizedResponse := func(t *testing.T, idp *mock.IdentityProvider, resp response, originalReferer string) {
 		assert.Equal(t, http.StatusUnauthorized, resp.StatusCode)
 		assert.Equal(t, loginURL(idp, originalReferer), resp.Location.String())
-		assert.Empty(t, resp.Body)
+		assert.Equal(t, "unauthenticated, please log in", resp.Body)
 	}
 
 	// assert that the request is proxied to the upstream, which returns a 401 unauthorized
@@ -147,7 +147,14 @@ func TestReverseProxy(t *testing.T) {
 				rpClient := idp.RelyingPartyClient()
 
 				resp := request(t, rpClient, method, idp.RelyingPartyServer.URL)
-				assertAutoLoginUnauthorizedResponse(t, idp, resp, "")
+
+				if method == http.MethodHead {
+					assert.Equal(t, http.StatusUnauthorized, resp.StatusCode)
+					assert.Equal(t, loginURL(idp, ""), resp.Location.String())
+					assert.Empty(t, resp.Body)
+				} else {
+					assertAutoLoginUnauthorizedResponse(t, idp, resp, "")
+				}
 			})
 		}
 	})
@@ -184,12 +191,39 @@ func TestReverseProxy(t *testing.T) {
 
 		target := idp.RelyingPartyServer.URL + "/some-path"
 
-		resp := get(t, rpClient, target,
-			header{"Sec-Fetch-Mode", ""},
-			header{"Sec-Fetch-Dest", ""},
-			header{"Accept", "text/html"},
-		)
-		assertAutoLoginRedirectResponse(t, idp, resp, "/some-path")
+		for _, tt := range []struct {
+			name    string
+			headers []header
+		}{
+			{"happy path", []header{
+				{"Accept", "text/html"},
+			}},
+			{"multiple values", []header{
+				{"Accept", "application/xhtml+xml, application/xml, text/html"},
+			}},
+			{"multiple accept headers", []header{
+				{"Accept", "application/xhtml+xml, application/xml;q=0.9"},
+				{"Accept", "text/plain"},
+				{"Accept", "text/html"},
+			}},
+			{"non-canonical value", []header{
+				{"Accept", ", text/HTML "},
+			}},
+			{"with quality parameter", []header{
+				{"Accept", "text/html;q=0.9"},
+			}},
+		} {
+			t.Run(tt.name, func(t *testing.T) {
+				noFetchMetadata := []header{
+					{"Sec-Fetch-Mode", ""},
+					{"Sec-Fetch-Dest", ""},
+				}
+				tt.headers = append(tt.headers, noFetchMetadata...)
+
+				resp := get(t, rpClient, target, tt.headers...)
+				assertAutoLoginRedirectResponse(t, idp, resp, "/some-path")
+			})
+		}
 	})
 
 	t.Run("with auto-login and ignored paths", func(t *testing.T) {