diff --git a/CHANGELOG.md b/CHANGELOG.md
index 0fcbd6f1b..5cb652cc0 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -10,6 +10,7 @@ Versioning: [Semantic Versioning](https://semver.org/spec/v2.0.0.html)
 ## [Unreleased]
 
 ### Fixed
+- **CLI files**: `files list` and `files upload` no longer crash with `TypeError: 'FileObject' object is not subscriptable` — `generate_file_table` and `upload` now read the OpenAI SDK's `FileObject` (a Pydantic model) via attribute access instead of dict-style subscripting.
 - **v2 message handling**: Preserve caller-owned message lists and nested content across request preparation and retries for OpenAI-compatible, Cohere, Mistral, OpenRouter, Writer, and xAI handlers. ([#2417](https://github.com/567-labs/instructor/issues/2417), [#2428](https://github.com/567-labs/instructor/issues/2428))
 - **v2 JSON extraction**: Prefer the final complete top-level JSON value in text responses and retain every JSON object when multiple objects arrive in one streaming chunk.
 - **v2 schemas**: Treat fields with Pydantic `default_factory` values as optional in generated OpenAI tool schemas.
diff --git a/instructor/cli/files.py b/instructor/cli/files.py
index c83d8929d..976c0c836 100644
--- a/instructor/cli/files.py
+++ b/instructor/cli/files.py
@@ -28,11 +28,11 @@ def generate_file_table(files: list[openai.types.FileObject]) -> Table:
 
     for file in files:
         table.add_row(
-            file["id"],
-            str(file["bytes"]),
-            str(datetime.fromtimestamp(file["created_at"])),
-            file["filename"],
-            file["purpose"],
+            file.id,
+            str(file.bytes),
+            str(datetime.fromtimestamp(file.created_at)),
+            file.filename,
+            file.purpose,
         )
 
     return table
@@ -61,7 +61,7 @@ def upload(
     file_purpose = cast(Literal["fine-tune", "assistants"], purpose)
     with open(filepath, "rb") as file:
         response = client.files.create(file=file, purpose=file_purpose)
-    file_id = response["id"]
+    file_id = response.id
     with console.status(f"Monitoring upload: {file_id}...") as status:
         status.spinner_style = "dots"
         while True:
diff --git a/tests/cli/test_files.py b/tests/cli/test_files.py
new file mode 100644
index 000000000..868934f4b
--- /dev/null
+++ b/tests/cli/test_files.py
@@ -0,0 +1,29 @@
+"""Tests for instructor.cli.files."""
+
+import os
+
+os.environ.setdefault("OPENAI_API_KEY", "test-key-for-cli-import")
+
+from openai.types import FileObject
+
+from instructor.cli.files import generate_file_table
+
+
+def test_generate_file_table_uses_attribute_access():
+    """FileObject (and other OpenAI SDK response objects) are Pydantic
+    models, not dicts — generate_file_table must read fields via attribute
+    access, not `file["id"]`-style subscripting, which raises TypeError."""
+    file = FileObject(
+        id="file-abc123",
+        bytes=1024,
+        created_at=1700000000,
+        filename="training.jsonl",
+        object="file",
+        purpose="fine-tune",
+        status="processed",
+    )
+
+    table = generate_file_table([file])
+
+    rendered_first_column = table.columns[0]._cells
+    assert list(rendered_first_column) == ["file-abc123"]