diff --git a/commands/server.go b/commands/server.go
index 708912fbb..57f96a1bd 100644
--- a/commands/server.go
+++ b/commands/server.go
@@ -150,14 +150,15 @@ func server(cmd *cobra.Command, args []string) {
 
 	// Watch runs its own server as part of the routine
 	if serverWatch {
-		watched := getDirList()
-		workingDir := helpers.AbsPathify(viper.GetString("WorkingDir"))
-		for i, dir := range watched {
-			watched[i], _ = helpers.GetRelativePath(dir, workingDir)
+		watchDirs := getDirList()
+		baseWatchDir := helpers.AbsPathify(viper.GetString("WorkingDir"))
+		for i, dir := range watchDirs {
+			watchDirs[i], _ = helpers.GetRelativePath(dir, baseWatchDir)
 		}
-		unique := strings.Join(helpers.RemoveSubpaths(watched), ",")
 
-		jww.FEEDBACK.Printf("Watching for changes in %s/{%s}\n", workingDir, unique)
+		rootWatchDirs := strings.Join(helpers.UniqueStrings(helpers.ExtractRootPaths(watchDirs)), ",")
+
+		jww.FEEDBACK.Printf("Watching for changes in %s/{%s}\n", baseWatchDir, rootWatchDirs)
 		err := NewWatcher(serverPort)
 		if err != nil {
 			fmt.Println(err)
diff --git a/helpers/general.go b/helpers/general.go
index b05c86092..eaf4e2d42 100644
--- a/helpers/general.go
+++ b/helpers/general.go
@@ -90,6 +90,19 @@ func FirstUpper(s string) string {
 	return string(unicode.ToUpper(r)) + s[n:]
 }
 
+// UniqueStrings returns a new slice with any duplicates removed.
+func UniqueStrings(s []string) []string {
+	unique := make([]string, 0)
+	set := map[string]interface{}{}
+	for _, val := range s {
+		if _, ok := set[val]; !ok {
+			unique = append(unique, val)
+			set[val] = val
+		}
+	}
+	return unique
+}
+
 // ReaderToBytes takes an io.Reader argument, reads from it
 // and returns bytes.
 func ReaderToBytes(lines io.Reader) []byte {
diff --git a/helpers/general_test.go b/helpers/general_test.go
index b4707b91e..4d85a1299 100644
--- a/helpers/general_test.go
+++ b/helpers/general_test.go
@@ -164,6 +164,15 @@ func _BenchmarkReaderContains(b *testing.B) {
 	}
 }
 
+func TestUniqueStrings(t *testing.T) {
+	in := []string{"a", "b", "a", "b", "c", "", "a", "", "d"}
+	output := UniqueStrings(in)
+	expected := []string{"a", "b", "c", "", "d"}
+	if !reflect.DeepEqual(output, expected) {
+		t.Errorf("Expected %#v, got %#v\n", expected, output)
+	}
+}
+
 func TestFindAvailablePort(t *testing.T) {
 	addr, err := FindAvailablePort()
 	assert.Nil(t, err)
diff --git a/helpers/path.go b/helpers/path.go
index 018c6fecb..07d08fa69 100644
--- a/helpers/path.go
+++ b/helpers/path.go
@@ -450,37 +450,27 @@ func prettifyPath(in string, b filepathPathBridge) string {
 	return b.Join(b.Dir(in), name, "index"+ext)
 }
 
-// RemoveSubpaths takes a list of paths and removes everything that
-// contains another path in the list as a prefix. Ignores any empty
-// strings. Used mostly for logging.
-//
-// e.g. ["hello/world", "hello", "foo/bar", ""] -> ["hello", "foo/bar"]
-func RemoveSubpaths(paths []string) []string {
-	a := make([]string, 0)
-	for _, cur := range paths {
-		// ignore trivial case
-		if cur == "" {
-			continue
-		}
-
-		isDupe := false
-		for i, old := range a {
-			if strings.HasPrefix(cur, old) {
-				isDupe = true
-				break
-			} else if strings.HasPrefix(old, cur) {
-				a[i] = cur
-				isDupe = true
-				break
+// Extract the root paths from the supplied list of paths.
+// The resulting root path will not contain any file separators, but there
+// may be duplicates.
+// So "/content/section/" becomes "content"
+func ExtractRootPaths(paths []string) []string {
+	r := make([]string, len(paths))
+	for i, p := range paths {
+		root := filepath.ToSlash(p)
+		if strings.Contains(root, "/") {
+			sections := strings.Split(root, "/")
+			for _, section := range sections {
+				if section != "" {
+					root = section
+					break
+				}
 			}
 		}
-
-		if !isDupe {
-			a = append(a, cur)
-		}
+		r[i] = root
 	}
+	return r
 
-	return a
 }
 
 // FindCWD returns the current working directory from where the Hugo
diff --git a/helpers/path_test.go b/helpers/path_test.go
index 9534cf9c1..a1d897df9 100644
--- a/helpers/path_test.go
+++ b/helpers/path_test.go
@@ -625,11 +625,19 @@ func TestPrettifyPath(t *testing.T) {
 
 }
 
-func TestRemoveSubpaths(t *testing.T) {
-	got := RemoveSubpaths([]string{"hello", "hello/world", "foo/bar", ""})
-	expect := []string{"hello", "foo/bar"}
-	if !reflect.DeepEqual(got, expect) {
-		t.Errorf("Expected %q but got %q", expect, got)
+func TestExtractRootPaths(t *testing.T) {
+	tests := []struct {
+		input    []string
+		expected []string
+	}{{[]string{filepath.FromSlash("a/b"), filepath.FromSlash("a/b/c/"), "b",
+		filepath.FromSlash("/c/d"), filepath.FromSlash("d/"), filepath.FromSlash("//e//")},
+		[]string{"a", "a", "b", "c", "d", "e"}}}
+
+	for _, test := range tests {
+		output := ExtractRootPaths(test.input)
+		if !reflect.DeepEqual(output, test.expected) {
+			t.Errorf("Expected %#v, got %#v\n", test.expected, output)
+		}
 	}
 }