diff --git a/.changelog/1c88b192e747436c998a32096006308c.json b/.changelog/1c88b192e747436c998a32096006308c.json
new file mode 100644
index 000000000000..6e03dd07889e
--- /dev/null
+++ b/.changelog/1c88b192e747436c998a32096006308c.json
@@ -0,0 +1,8 @@
+{
+    "id": "1c88b192-e747-436c-998a-32096006308c",
+    "type": "bugfix",
+    "description": "Loose download directory check to allow downloading objects with double dot in filename",
+    "modules": [
+        "feature/s3/transfermanager"
+    ]
+}
\ No newline at end of file
diff --git a/feature/s3/transfermanager/api_op_DownloadDirectory.go b/feature/s3/transfermanager/api_op_DownloadDirectory.go
index c151f49b8aa0..c244ba93fc6d 100644
--- a/feature/s3/transfermanager/api_op_DownloadDirectory.go
+++ b/feature/s3/transfermanager/api_op_DownloadDirectory.go
@@ -236,7 +236,7 @@ func (d *directoryDownloader) getLocalPath(key string) (string, error) {
 	if err != nil {
 		return "", err
 	}
-	if relPath == "." || strings.Contains(relPath, "..") {
+	if relPath == "." || !filepath.IsLocal(relPath) {
 		return "", fmt.Errorf("resolved local path %s is outside of destination %s", path, destination)
 	}
 
diff --git a/feature/s3/transfermanager/download_directory_test.go b/feature/s3/transfermanager/download_directory_test.go
index 585bc467c9d4..3983c864c7f9 100644
--- a/feature/s3/transfermanager/download_directory_test.go
+++ b/feature/s3/transfermanager/download_directory_test.go
@@ -280,6 +280,46 @@ func TestDownloadDirectory(t *testing.T) {
 				l.expectFailed(t, in, err)
 			},
 		},
+		"object key with double dots in name and path": {
+			destination: "double-dots-in-name-and-path",
+			objectsLists: [][]s3types.Object{
+				{
+					{
+						Key: aws.String("foo/bar/../baz..zoo"),
+					},
+					{
+						Key: aws.String("a..b"),
+					},
+				},
+			},
+			expectTokens:            []string{""},
+			expectKeys:              []string{"foo/bar/../baz..zoo", "a..b"},
+			expectFiles:             []string{"foo/baz..zoo", "a..b"},
+			expectObjectsDownloaded: 2,
+			listenerValidationFn: func(t *testing.T, l *mockDirectoryListener, in, out any, err error) {
+				l.expectStart(t, in)
+				l.expectComplete(t, in, out, 2)
+			},
+		},
+		"object key with double dots in name and path escaping": {
+			destination: "double-dots-in-name-and-path-escaping",
+			objectsLists: [][]s3types.Object{
+				{
+					{
+						Key: aws.String("foo/../../baz..zoo"),
+					},
+					{
+						Key: aws.String("a..b"),
+					},
+				},
+			},
+			expectErr: "outside of destination",
+			listenerValidationFn: func(t *testing.T, l *mockDirectoryListener, in, out any, err error) {
+				// only validate failure listener since start listener
+				// might never be triggerred if the error response is returned first
+				l.expectFailed(t, in, err)
+			},
+		},
 		"multiple objects with filter applied": {
 			destination: "multiple-objects-with-filter-applied",
 			objectsLists: [][]s3types.Object{