diff --git a/README.md b/README.md
index 7270a5281..5e04aa7e5 100644
--- a/README.md
+++ b/README.md
@@ -247,7 +247,7 @@ Error codes are as follows:
 
 Certain errors are automatically retried 5 times by default, with a short exponential backoff.
 Connection errors (for example, due to a network connectivity problem), 408 Request Timeout, 409 Conflict,
-429 Rate Limit, and >=500 Internal errors are all retried by default for GET requests. For POST requests, only 
+429 Rate Limit, and >=500 Internal errors are all retried by default for GET requests. For POST requests, only
 429 errors will be retried.
 
 You can use the `max_retries` option to configure or disable retry settings:
@@ -265,6 +265,35 @@ client = Runloop(
 client.with_options(max_retries=10).devboxes.create()
 ```
 
+#### File Write Rate Limiting
+
+File write operations (`write_file_contents` and `upload_file`) are subject to rate limiting on the backend
+(approximately 80 chunks per second, equivalent to ~10MB/sec per connection). When rate limits are exceeded,
+the API returns a `429 Too Many Requests` error, which is automatically retried with exponential backoff.
+
+The retry behavior includes:
+- **Default retries**: 5 attempts (initial request + 4 retries)
+- **Backoff strategy**: Exponential with jitter to prevent thundering herd
+- **Retry-After header**: Respected when provided by the API
+- **Configurable**: Use `max_retries` parameter to adjust retry behavior
+
+Example:
+```python
+from runloop_api_client import Runloop
+
+client = Runloop(
+    bearer_token="your-api-key",
+    max_retries=5  # Recommended for file operations
+)
+
+# Automatically retries on rate limit errors
+result = client.devboxes.write_file_contents(
+    id="devbox-id",
+    contents="large file content...",
+    file_path="/path/to/file.txt"
+)
+```
+
 ### Timeouts
 
 By default requests time out after 30 seconds. You can configure this with a `timeout` option,
diff --git a/src/runloop_api_client/resources/devboxes/devboxes.py b/src/runloop_api_client/resources/devboxes/devboxes.py
index 4a8bffe9e..78d15b510 100644
--- a/src/runloop_api_client/resources/devboxes/devboxes.py
+++ b/src/runloop_api_client/resources/devboxes/devboxes.py
@@ -718,7 +718,7 @@ def execute(
         id: str,
         *,
         command: str,
-        command_id: str,
+        command_id: str = str(uuid7()),
         optimistic_timeout: Optional[int] | Omit = omit,
         shell_name: Optional[str] | Omit = omit,
         # Use the following arguments if you need to pass additional parameters to the API that aren't available via kwargs.
@@ -897,6 +897,7 @@ def execute_async(
         )
 
     @typing_extensions.deprecated("deprecated")
+    # Use execute, executeAsync, or executeAndAwaitCompletion instead
     def execute_sync(
         self,
         id: str,
@@ -915,6 +916,9 @@ def execute_sync(
         Execute a bash command in the Devbox shell, await the command completion and
         return the output.
 
+        .. deprecated::
+           Use execute, executeAsync, or executeAndAwaitCompletion instead.
+
         Args:
           command: The command to execute via the Devbox shell. By default, commands are run from
               the user home directory unless shell_name is specified. If shell_name is
@@ -2161,7 +2165,7 @@ async def execute(
         id: str,
         *,
         command: str,
-        command_id: str,
+        command_id: str = str(uuid7()),
         optimistic_timeout: Optional[int] | Omit = omit,
         shell_name: Optional[str] | Omit = omit,
         # Use the following arguments if you need to pass additional parameters to the API that aren't available via kwargs.
@@ -2341,6 +2345,7 @@ async def execute_async(
         )
 
     @typing_extensions.deprecated("deprecated")
+    # Use execute, executeAsync, or executeAndAwaitCompletion instead
     async def execute_sync(
         self,
         id: str,
@@ -2359,6 +2364,9 @@ async def execute_sync(
         Execute a bash command in the Devbox shell, await the command completion and
         return the output.
 
+        .. deprecated::
+           Use execute, executeAsync, or executeAndAwaitCompletion instead.
+
         Args:
           command: The command to execute via the Devbox shell. By default, commands are run from
               the user home directory unless shell_name is specified. If shell_name is
diff --git a/tests/test_rate_limit_retry.py b/tests/test_rate_limit_retry.py
new file mode 100644
index 000000000..82eceb555
--- /dev/null
+++ b/tests/test_rate_limit_retry.py
@@ -0,0 +1,343 @@
+"""Tests for rate limit retry behavior on file write operations."""
+
+from __future__ import annotations
+
+import time
+from typing import Any
+from unittest.mock import Mock, patch
+
+import httpx
+import pytest
+import respx
+
+from runloop_api_client import Runloop, AsyncRunloop
+from runloop_api_client._exceptions import RateLimitError
+from runloop_api_client.types import DevboxExecutionDetailView
+
+base_url = "http://127.0.0.1:4010"
+
+
+class TestRateLimitRetry:
+    """Test rate limit retry behavior for file write operations."""
+
+    def test_write_file_contents_retries_on_429(self, respx_mock: respx.MockRouter) -> None:
+        """Test that write_file_contents retries when encountering 429 errors."""
+        client = Runloop(base_url=base_url, bearer_token="test-token", max_retries=3)
+
+        # Mock the first two requests to return 429, then succeed
+        route = respx_mock.post(f"{base_url}/v1/devboxes/test-devbox-id/write_file_contents")
+
+        route.side_effect = [
+            # First attempt: 429
+            httpx.Response(
+                status_code=429,
+                json={
+                    "error": {
+                        "message": "Write operations for this devbox are currently rate limited. Please retry in a few seconds."
+                    }
+                },
+            ),
+            # Second attempt: 429
+            httpx.Response(
+                status_code=429,
+                json={
+                    "error": {
+                        "message": "Write operations for this devbox are currently rate limited. Please retry in a few seconds."
+                    }
+                },
+            ),
+            # Third attempt: success
+            httpx.Response(
+                status_code=200,
+                json={
+                    "id": "exec-123",
+                    "devbox_id": "test-devbox-id",
+                    "status": "completed",
+                    "exit_status": 0,
+                },
+            ),
+        ]
+
+        start_time = time.time()
+        result = client.devboxes.write_file_contents(
+            id="test-devbox-id",
+            contents="test content",
+            file_path="/tmp/test.txt",
+        )
+        elapsed_time = time.time() - start_time
+
+        # Verify the request succeeded
+        assert result.id == "exec-123"
+        assert result.status == "completed"
+
+        # Verify retry happened (should have taken at least some time due to backoff)
+        assert elapsed_time > 0.1  # At least some delay from retries
+
+        # Verify all three requests were made
+        assert route.call_count == 3
+
+    def test_write_file_contents_respects_retry_after_header(self, respx_mock: respx.MockRouter) -> None:
+        """Test that write_file_contents respects Retry-After header."""
+        client = Runloop(base_url=base_url, bearer_token="test-token", max_retries=2)
+
+        route = respx_mock.post(f"{base_url}/v1/devboxes/test-devbox-id/write_file_contents")
+
+        route.side_effect = [
+            # First attempt: 429 with Retry-After header
+            httpx.Response(
+                status_code=429,
+                headers={"Retry-After": "1"},  # Retry after 1 second
+                json={
+                    "error": {
+                        "message": "Write operations for this devbox are currently rate limited."
+                    }
+                },
+            ),
+            # Second attempt: success
+            httpx.Response(
+                status_code=200,
+                json={
+                    "id": "exec-456",
+                    "devbox_id": "test-devbox-id",
+                    "status": "completed",
+                    "exit_status": 0,
+                },
+            ),
+        ]
+
+        start_time = time.time()
+        result = client.devboxes.write_file_contents(
+            id="test-devbox-id",
+            contents="test content",
+            file_path="/tmp/test.txt",
+        )
+        elapsed_time = time.time() - start_time
+
+        # Verify the request succeeded
+        assert result.id == "exec-456"
+
+        # Verify it waited approximately 1 second (Retry-After value)
+        assert elapsed_time >= 0.9  # Allow slight timing variance
+        assert elapsed_time < 2.0  # Should not take too long
+
+        # Verify two requests were made
+        assert route.call_count == 2
+
+    def test_write_file_contents_exhausts_retries(self, respx_mock: respx.MockRouter) -> None:
+        """Test that write_file_contents fails after exhausting retries."""
+        client = Runloop(base_url=base_url, bearer_token="test-token", max_retries=2)
+
+        route = respx_mock.post(f"{base_url}/v1/devboxes/test-devbox-id/write_file_contents")
+
+        # All attempts return 429
+        for _ in range(3):  # max_retries + 1
+            route.mock(
+                return_value=httpx.Response(
+                    status_code=429,
+                    json={
+                        "error": {
+                            "message": "Write operations for this devbox are currently rate limited."
+                        }
+                    },
+                )
+            )
+
+        # Should raise RateLimitError after exhausting retries
+        with pytest.raises(RateLimitError) as exc_info:
+            client.devboxes.write_file_contents(
+                id="test-devbox-id",
+                contents="test content",
+                file_path="/tmp/test.txt",
+            )
+
+        # Verify error message
+        assert "rate limit" in str(exc_info.value).lower()
+
+        # Verify all retry attempts were made
+        assert route.call_count == 3  # initial + 2 retries
+
+    def test_upload_file_retries_on_429(self, respx_mock: respx.MockRouter) -> None:
+        """Test that upload_file retries when encountering 429 errors."""
+        client = Runloop(base_url=base_url, bearer_token="test-token", max_retries=3)
+
+        route = respx_mock.post(f"{base_url}/v1/devboxes/test-devbox-id/upload_file")
+
+        route.side_effect = [
+            # First attempt: 429
+            httpx.Response(
+                status_code=429,
+                json={
+                    "error": {
+                        "message": "Write operations for this devbox are currently rate limited."
+                    }
+                },
+            ),
+            # Second attempt: success
+            httpx.Response(
+                status_code=200,
+                json={"success": True},
+            ),
+        ]
+
+        result = client.devboxes.upload_file(
+            id="test-devbox-id",
+            path="/tmp/test.bin",
+            file=b"binary content",
+        )
+
+        # Verify the request succeeded
+        assert result == {"success": True}
+
+        # Verify retry happened
+        assert route.call_count == 2
+
+    def test_write_file_contents_with_custom_max_retries(self, respx_mock: respx.MockRouter) -> None:
+        """Test that custom max_retries configuration is respected."""
+        client = Runloop(base_url=base_url, bearer_token="test-token", max_retries=5)
+
+        route = respx_mock.post(f"{base_url}/v1/devboxes/test-devbox-id/write_file_contents")
+
+        # Return 429 for first 4 attempts, then succeed
+        route.side_effect = [
+            httpx.Response(status_code=429, json={"error": {"message": "Rate limited"}}),
+            httpx.Response(status_code=429, json={"error": {"message": "Rate limited"}}),
+            httpx.Response(status_code=429, json={"error": {"message": "Rate limited"}}),
+            httpx.Response(status_code=429, json={"error": {"message": "Rate limited"}}),
+            httpx.Response(
+                status_code=200,
+                json={
+                    "id": "exec-789",
+                    "devbox_id": "test-devbox-id",
+                    "status": "completed",
+                    "exit_status": 0,
+                },
+            ),
+        ]
+
+        result = client.devboxes.write_file_contents(
+            id="test-devbox-id",
+            contents="test content",
+            file_path="/tmp/test.txt",
+        )
+
+        # Verify success after 5 attempts (initial + 4 retries)
+        assert result.id == "exec-789"
+        assert route.call_count == 5
+
+    def test_write_file_contents_no_retry_when_disabled(self, respx_mock: respx.MockRouter) -> None:
+        """Test that retries can be disabled by setting max_retries=0."""
+        client = Runloop(base_url=base_url, bearer_token="test-token", max_retries=0)
+
+        route = respx_mock.post(f"{base_url}/v1/devboxes/test-devbox-id/write_file_contents")
+        route.mock(
+            return_value=httpx.Response(
+                status_code=429,
+                json={"error": {"message": "Rate limited"}},
+            )
+        )
+
+        # Should fail immediately without retry
+        with pytest.raises(RateLimitError):
+            client.devboxes.write_file_contents(
+                id="test-devbox-id",
+                contents="test content",
+                file_path="/tmp/test.txt",
+            )
+
+        # Verify only one request was made (no retries)
+        assert route.call_count == 1
+
+
+class TestAsyncRateLimitRetry:
+    """Test async rate limit retry behavior for file write operations."""
+
+    @pytest.mark.asyncio
+    async def test_write_file_contents_retries_on_429(self, respx_mock: respx.MockRouter) -> None:
+        """Test that async write_file_contents retries when encountering 429 errors."""
+        client = AsyncRunloop(base_url=base_url, bearer_token="test-token", max_retries=3)
+
+        route = respx_mock.post(f"{base_url}/v1/devboxes/test-devbox-id/write_file_contents")
+
+        route.side_effect = [
+            # First two attempts: 429
+            httpx.Response(status_code=429, json={"error": {"message": "Rate limited"}}),
+            httpx.Response(status_code=429, json={"error": {"message": "Rate limited"}}),
+            # Third attempt: success
+            httpx.Response(
+                status_code=200,
+                json={
+                    "id": "exec-async-123",
+                    "devbox_id": "test-devbox-id",
+                    "status": "completed",
+                    "exit_status": 0,
+                },
+            ),
+        ]
+
+        start_time = time.time()
+        result = await client.devboxes.write_file_contents(
+            id="test-devbox-id",
+            contents="test content",
+            file_path="/tmp/test.txt",
+        )
+        elapsed_time = time.time() - start_time
+
+        # Verify the request succeeded
+        assert result.id == "exec-async-123"
+
+        # Verify retry happened (should have taken some time)
+        assert elapsed_time > 0.1
+
+        # Verify all three requests were made
+        assert route.call_count == 3
+
+    @pytest.mark.asyncio
+    async def test_upload_file_retries_on_429(self, respx_mock: respx.MockRouter) -> None:
+        """Test that async upload_file retries when encountering 429 errors."""
+        client = AsyncRunloop(base_url=base_url, bearer_token="test-token", max_retries=2)
+
+        route = respx_mock.post(f"{base_url}/v1/devboxes/test-devbox-id/upload_file")
+
+        route.side_effect = [
+            # First attempt: 429
+            httpx.Response(status_code=429, json={"error": {"message": "Rate limited"}}),
+            # Second attempt: success
+            httpx.Response(status_code=200, json={"success": True}),
+        ]
+
+        result = await client.devboxes.upload_file(
+            id="test-devbox-id",
+            path="/tmp/test.bin",
+            file=b"binary content",
+        )
+
+        # Verify the request succeeded
+        assert result == {"success": True}
+        assert route.call_count == 2
+
+    @pytest.mark.asyncio
+    async def test_write_file_contents_exhausts_retries(self, respx_mock: respx.MockRouter) -> None:
+        """Test that async write_file_contents fails after exhausting retries."""
+        client = AsyncRunloop(base_url=base_url, bearer_token="test-token", max_retries=2)
+
+        route = respx_mock.post(f"{base_url}/v1/devboxes/test-devbox-id/write_file_contents")
+
+        # All attempts return 429
+        for _ in range(3):
+            route.mock(
+                return_value=httpx.Response(
+                    status_code=429,
+                    json={"error": {"message": "Rate limited"}},
+                )
+            )
+
+        # Should raise RateLimitError
+        with pytest.raises(RateLimitError):
+            await client.devboxes.write_file_contents(
+                id="test-devbox-id",
+                contents="test content",
+                file_path="/tmp/test.txt",
+            )
+
+        # Verify all retry attempts were made
+        assert route.call_count == 3