diff --git a/backend/s3/s3.go b/backend/s3/s3.go
index 1898cf969..eb5e879c2 100644
--- a/backend/s3/s3.go
+++ b/backend/s3/s3.go
@@ -1923,20 +1923,52 @@ func NewFs(ctx context.Context, name, root string, m configmap.Mapper) (fs.Fs, e
 		newRoot, leaf := path.Split(oldRoot)
 		f.setRoot(newRoot)
 		_, err := f.NewObject(ctx, leaf)
-		if errors.Is(err, fs.ErrorObjectNotFound) {
+		switch {
+		case err == nil:
+			// It is a file so return an fs which points to the parent
+			return f, fs.ErrorIsFile
+		case errors.Is(err, fs.ErrorObjectNotFound):
 			// File doesn't exist or is a directory so return old f
 			f.setRoot(oldRoot)
 			return f, nil
+		default:
+			// We couldn't HEAD the object so now attempt to list it
+			hasChildren, listErr := f.hasChildren(ctx, leaf)
+			if listErr != nil {
+				fs.Debugf(f, "Couldn't check %q for children after HEAD failed (%v): %v", oldRoot, err, listErr)
+			}
+			// If it listed and has children it must be a directory
+			if hasChildren {
+				f.setRoot(oldRoot)
+				return f, nil
+			}
+			// If it has no children it is either a file or an empty directory. We can't
+			// tell these two cases apart. We choose file which is more likely, and
+			// return an fs which points to the parent.
+			return f, fs.ErrorIsFile
 		}
-		if err != nil {
-			return nil, err
-		}
-		// return an error with an fs which points to the parent
-		return f, fs.ErrorIsFile
 	}
 	return f, nil
 }
 
+// hasChildren reports whether the directory dir contains any objects.
+func (f *Fs) hasChildren(ctx context.Context, dir string) (found bool, err error) {
+	bucket, directory := f.split(dir)
+	err = f.list(ctx, listOpt{
+		bucket:    bucket,
+		directory: directory,
+		prefix:    f.rootDirectory,
+		recurse:   true,
+	}, func(remote string, object *types.Object, versionID *string, isDirectory bool) error {
+		found = true
+		return errEndList // stop after the first object
+	})
+	if err != nil && err != fs.ErrorDirNotFound {
+		return false, err
+	}
+	return found, nil
+}
+
 // getMetaDataListing gets the metadata from the object unconditionally from the listing
 //
 // This is needed to find versioned objects from their paths.
diff --git a/backend/s3/s3_internal_test.go b/backend/s3/s3_internal_test.go
index 5a67ffbdb..1a719d899 100644
--- a/backend/s3/s3_internal_test.go
+++ b/backend/s3/s3_internal_test.go
@@ -144,6 +144,31 @@ func (f *Fs) InternalTestNoHead(t *testing.T) {
 
 }
 
+func (f *Fs) InternalTestHasChildren(t *testing.T) {
+	ctx := context.Background()
+	contents := random.String(100)
+	item := fstest.NewItem("has-children/file.txt", contents, fstest.Time("2001-05-06T04:05:06.499999999Z"))
+	obj := fstests.PutTestContents(ctx, t, f, &item, contents, true)
+	defer func() {
+		assert.NoError(t, obj.Remove(ctx))
+	}()
+
+	// A prefix with an object under it is a directory
+	found, err := f.hasChildren(ctx, "has-children")
+	require.NoError(t, err)
+	assert.True(t, found, "prefix with an object should report children")
+
+	// The object itself is a file so has no children
+	found, err = f.hasChildren(ctx, "has-children/file.txt")
+	require.NoError(t, err)
+	assert.False(t, found, "a file should not report children")
+
+	// A path which doesn't exist has no children
+	found, err = f.hasChildren(ctx, "has-children/does-not-exist")
+	require.NoError(t, err)
+	assert.False(t, found, "a missing path should not report children")
+}
+
 func TestVersionLess(t *testing.T) {
 	key1 := "key1"
 	key2 := "key2"
@@ -785,6 +810,7 @@ func (f *Fs) InternalTestObjectLock(t *testing.T) {
 func (f *Fs) InternalTest(t *testing.T) {
 	t.Run("Metadata", f.InternalTestMetadata)
 	t.Run("NoHead", f.InternalTestNoHead)
+	t.Run("HasChildren", f.InternalTestHasChildren)
 	t.Run("Versions", f.InternalTestVersions)
 	t.Run("ObjectLock", f.InternalTestObjectLock)
 }