diff --git a/homeassistant/components/onedrive/services.py b/homeassistant/components/onedrive/services.py
index 1e579b82a0fc2..87539a032822f 100644
--- a/homeassistant/components/onedrive/services.py
+++ b/homeassistant/components/onedrive/services.py
@@ -42,7 +42,7 @@ def _read_file_contents(
     hass: HomeAssistant, filenames: list[str]
 ) -> list[tuple[str, bytes]]:
     """Return the mime types and file contents for each file."""
-    results = []
+    missing: list[str] = []
     for filename in filenames:
         if not hass.config.is_allowed_path(filename):
             raise HomeAssistantError(
@@ -50,20 +50,27 @@ def _read_file_contents(
                 translation_key="no_access_to_path",
                 translation_placeholders={"filename": filename},
             )
+        if not Path(filename).exists():
+            missing.append(filename)
+    if missing:
+        raise HomeAssistantError(
+            translation_domain=DOMAIN,
+            translation_key="filenames_do_not_exist",
+            translation_placeholders={
+                "filenames": ", ".join(f"`{f}`" for f in missing)
+            },
+        )
+    results = []
+    for filename in filenames:
         filename_path = Path(filename)
-        if not filename_path.exists():
-            raise HomeAssistantError(
-                translation_domain=DOMAIN,
-                translation_key="filename_does_not_exist",
-                translation_placeholders={"filename": filename},
-            )
-        if filename_path.stat().st_size > CONTENT_SIZE_LIMIT:
+        file_size = filename_path.stat().st_size
+        if file_size > CONTENT_SIZE_LIMIT:
             raise HomeAssistantError(
                 translation_domain=DOMAIN,
                 translation_key="file_too_large",
                 translation_placeholders={
                     "filename": filename,
-                    "size": str(filename_path.stat().st_size),
+                    "size": str(file_size),
                     "limit": str(CONTENT_SIZE_LIMIT),
                 },
             )
diff --git a/homeassistant/components/onedrive/strings.json b/homeassistant/components/onedrive/strings.json
index 028d41d8bcc6e..1f1aa5ec38924 100644
--- a/homeassistant/components/onedrive/strings.json
+++ b/homeassistant/components/onedrive/strings.json
@@ -102,8 +102,8 @@
     "file_too_large": {
       "message": "`{filename}` is too large ({size} > {limit})"
     },
-    "filename_does_not_exist": {
-      "message": "`{filename}` does not exist"
+    "filenames_do_not_exist": {
+      "message": "The following files do not exist: {filenames}"
     },
     "no_access_to_path": {
       "message": "Cannot read {filename}, no access to path; `allowlist_external_dirs` may need to be adjusted in `configuration.yaml`"
diff --git a/tests/components/onedrive/test_services.py b/tests/components/onedrive/test_services.py
index df50a32b6877c..cb0bb8721ed44 100644
--- a/tests/components/onedrive/test_services.py
+++ b/tests/components/onedrive/test_services.py
@@ -194,7 +194,7 @@ async def test_filename_does_not_exist(
 ) -> None:
     """Test upload service call with a filename path that does not exist."""
     await setup_integration(hass, mock_config_entry)
-    with pytest.raises(HomeAssistantError, match="does not exist"):
+    with pytest.raises(HomeAssistantError) as exc_info:
         await hass.services.async_call(
             DOMAIN,
             UPLOAD_SERVICE,
@@ -206,6 +206,33 @@ async def test_filename_does_not_exist(
             blocking=True,
             return_response=True,
         )
+    assert exc_info.value.translation_key == "filenames_do_not_exist"
+    assert TEST_FILENAME in exc_info.value.translation_placeholders["filenames"]
+
+
+@pytest.mark.parametrize("upload_file", [MockUploadFile(exists=False)])
+async def test_multiple_filenames_do_not_exist(
+    hass: HomeAssistant,
+    mock_config_entry: MockConfigEntry,
+) -> None:
+    """Test upload service reports all missing files, not just the first one."""
+    await setup_integration(hass, mock_config_entry)
+    second_filename = "other_snapshot.jpg"
+    with pytest.raises(HomeAssistantError) as exc_info:
+        await hass.services.async_call(
+            DOMAIN,
+            UPLOAD_SERVICE,
+            {
+                CONF_CONFIG_ENTRY_ID: mock_config_entry.entry_id,
+                CONF_FILENAME: [TEST_FILENAME, second_filename],
+                CONF_DESTINATION_FOLDER: DESINATION_FOLDER,
+            },
+            blocking=True,
+            return_response=True,
+        )
+    assert exc_info.value.translation_key == "filenames_do_not_exist"
+    assert TEST_FILENAME in exc_info.value.translation_placeholders["filenames"]
+    assert second_filename in exc_info.value.translation_placeholders["filenames"]
 
 
 async def test_upload_service_fails_upload(