diff --git a/caddyhttp/push/handler.go b/caddyhttp/push/handler.go
index a651338e..fcc6ab0b 100644
--- a/caddyhttp/push/handler.go
+++ b/caddyhttp/push/handler.go
@@ -5,6 +5,7 @@ import (
 	"strings"
 
 	"github.com/mholt/caddy/caddyhttp/httpserver"
+	"github.com/mholt/caddy/caddyhttp/staticfiles"
 )
 
 func (h Middleware) ServeHTTP(w http.ResponseWriter, r *http.Request) (int, error) {
@@ -25,7 +26,13 @@ func (h Middleware) ServeHTTP(w http.ResponseWriter, r *http.Request) (int, erro
 	// push first
 outer:
 	for _, rule := range h.Rules {
-		if httpserver.Path(r.URL.Path).Matches(rule.Path) {
+		urlPath := r.URL.Path
+		matches := httpserver.Path(urlPath).Matches(rule.Path)
+		// Also check IndexPages when requesting a directory
+		if !matches {
+			_, matches = httpserver.IndexFile(h.Root, urlPath, staticfiles.IndexPages)
+		}
+		if matches {
 			for _, resource := range rule.Resources {
 				pushErr := pusher.Push(resource.Path, &http.PushOptions{
 					Method: resource.Method,
diff --git a/caddyhttp/push/handler_test.go b/caddyhttp/push/handler_test.go
index 343ab746..40903b6f 100644
--- a/caddyhttp/push/handler_test.go
+++ b/caddyhttp/push/handler_test.go
@@ -2,8 +2,11 @@ package push
 
 import (
 	"errors"
+	"io/ioutil"
 	"net/http"
 	"net/http/httptest"
+	"os"
+	"path/filepath"
 	"reflect"
 	"testing"
 
@@ -307,6 +310,63 @@ func TestMiddlewareShouldInterceptLinkHeaderPusherError(t *testing.T) {
 	comparePushedResources(t, expectedPushedResources, pushingWriter.pushed)
 }
 
+func TestMiddlewareShouldPushIndexFile(t *testing.T) {
+	// given
+	indexFile := "/index.html"
+	request, err := http.NewRequest(http.MethodGet, "/", nil) // Request root directory, not indexfile itself
+	if err != nil {
+		t.Fatalf("Could not create HTTP request: %v", err)
+	}
+
+	root, err := ioutil.TempDir("", "caddy")
+	if err != nil {
+		t.Fatalf("Could not create temporary directory: %v", err)
+	}
+	defer os.Remove(root)
+
+	middleware := Middleware{
+		Next: httpserver.HandlerFunc(func(w http.ResponseWriter, r *http.Request) (int, error) {
+			return 0, nil
+		}),
+		Rules: []Rule{
+			{Path: indexFile, Resources: []Resource{
+				{Path: "/index.css", Method: http.MethodGet},
+			}},
+		},
+		Root: http.Dir(root),
+	}
+
+	indexFilePath := filepath.Join(root, indexFile)
+	_, err = os.Create(indexFilePath)
+	if err != nil {
+		t.Fatalf("Could not create index file: %s: %v", indexFile, err)
+	}
+	defer os.Remove(indexFilePath)
+
+	pushingWriter := &MockedPusher{
+		ResponseWriter: httptest.NewRecorder(),
+		returnedError:  errors.New("Cannot push right now"),
+	}
+
+	// when
+	_, err2 := middleware.ServeHTTP(pushingWriter, request)
+
+	// then
+	if err2 != nil {
+		t.Error("Should not return error")
+	}
+
+	expectedPushedResources := map[string]*http.PushOptions{
+		"/index.css": {
+			Method: http.MethodGet,
+			Header: http.Header{},
+		},
+	}
+
+	comparePushedResources(t, expectedPushedResources, pushingWriter.pushed)
+
+}
+
 func comparePushedResources(t *testing.T, expected, actual map[string]*http.PushOptions) {
 	if len(expected) != len(actual) {
 		t.Errorf("Expected %d pushed resources, actual: %d", len(expected), len(actual))
diff --git a/caddyhttp/push/push.go b/caddyhttp/push/push.go
index b2063bd7..2c5821a5 100644
--- a/caddyhttp/push/push.go
+++ b/caddyhttp/push/push.go
@@ -24,6 +24,7 @@ type (
 	Middleware struct {
 		Next  httpserver.Handler
 		Rules []Rule
+		Root  http.FileSystem
 	}
 
 	ruleOp func([]Resource)
diff --git a/caddyhttp/push/setup.go b/caddyhttp/push/setup.go
index b6c33176..28e8dbc5 100644
--- a/caddyhttp/push/setup.go
+++ b/caddyhttp/push/setup.go
@@ -34,8 +34,9 @@ func setup(c *caddy.Controller) error {
 		return err
 	}
 
-	httpserver.GetConfig(c).AddMiddleware(func(next httpserver.Handler) httpserver.Handler {
-		return Middleware{Next: next, Rules: rules}
+	cfg := httpserver.GetConfig(c)
+	cfg.AddMiddleware(func(next httpserver.Handler) httpserver.Handler {
+		return Middleware{Next: next, Rules: rules, Root: http.Dir(cfg.Root)}
 	})
 
 	return nil