diff --git a/dvc/output.py b/dvc/output.py
index 4138499da..a2a7e5907 100644
--- a/dvc/output.py
+++ b/dvc/output.py
@@ -327,7 +327,9 @@ class Output:
         meta = Meta.from_dict(info or {})
         # NOTE: when version_aware is not passed into get_cloud_fs, it will be
         # set based on whether or not path is versioned
-        fs_kwargs = {"version_aware": True} if meta.version_id else {}
+        fs_kwargs = {}
+        if meta.version_id or files:
+            fs_kwargs["version_aware"] = True
 
         if fs_config is not None:
             fs_kwargs.update(**fs_config)
diff --git a/tests/unit/output/test_output.py b/tests/unit/output/test_output.py
index 7f2135cd6..0eb3b1c34 100644
--- a/tests/unit/output/test_output.py
+++ b/tests/unit/output/test_output.py
@@ -176,3 +176,30 @@ def test_dumpd_cloud_versioning_dir(mocker):
 
     dumpd = out.dumpd()
     assert dumpd == {"path": "path", "files": files}
+
+
+def test_version_aware_is_set_based_on_files(mocker):
+    import dvc.fs as dvc_fs
+
+    get_fs_config = mocker.spy(dvc_fs, "get_fs_config")
+
+    stage = mocker.MagicMock()
+    stage.repo.fs.version_aware = False
+    stage.repo.fs.PARAM_CHECKSUM = "etag"
+    files = [
+        {
+            "size": 3,
+            "version_id": "WYRG4BglP7pD.gEoJP6a4AqOhl.FRA.h",
+            "etag": "acbd18db4cc2f85cedef654fccc4a4d8",
+            "md5": "acbd18db4cc2f85cedef654fccc4a4d8",
+            "relpath": "bar",
+        }
+    ]
+    Output(stage, "path", files=files)
+    # version_aware is passed as `True` if `files` is present`.
+    # This will be intentionally ignored in filesystems that don't handle it
+    # in `_prepare_credentials`.
+    assert get_fs_config.call_args_list[0][1] == {
+        "url": "path",
+        "version_aware": True,
+    }