diff --git a/.gitattributes b/.gitattributes
index 5c9061f52ac..7127d1daae1 100644
--- a/.gitattributes
+++ b/.gitattributes
@@ -1,2 +1,6 @@
 *.ipynb linguist-vendored
-ui/litellm-dashboard/src/lib/http/schema.d.ts linguist-generated
\ No newline at end of file
+ui/litellm-dashboard/src/lib/http/schema.d.ts linguist-generated
+# tiktoken rejects these caches unless they are byte-exact, and Windows checkouts would convert them to CRLF
+litellm/litellm_core_utils/tokenizers/9b5ad71b2ce5302211f9c61530b329a4922fc6a4 binary
+litellm/litellm_core_utils/tokenizers/ec7223a39ce59f226a68acc30dc1af2788490e15 binary
+litellm/litellm_core_utils/tokenizers/fb374d419588a4632f3f557e76b4b70aebbca790 binary
diff --git a/tests/windows_tests/test_bundled_tiktoken_caches.py b/tests/windows_tests/test_bundled_tiktoken_caches.py
new file mode 100644
index 00000000000..042d4969513
--- /dev/null
+++ b/tests/windows_tests/test_bundled_tiktoken_caches.py
@@ -0,0 +1,58 @@
+import importlib.util
+import re
+import shutil
+import subprocess
+from pathlib import Path
+
+import pytest
+import tiktoken.load
+from tiktoken_ext import openai_public
+
+REPO_ROOT = Path(__file__).resolve().parents[2]
+TOKENIZERS = Path("litellm", "litellm_core_utils", "tokenizers")
+TIKTOKEN_CACHE_FILE_NAME = re.compile(r"[0-9a-f]{40}")
+
+
+def _tokenizers_dir_without_importing_litellm() -> Path:
+    spec = importlib.util.find_spec("litellm")
+    assert spec is not None and spec.submodule_search_locations
+    return Path(next(iter(spec.submodule_search_locations))).joinpath(*TOKENIZERS.parts[1:])
+
+
+@pytest.mark.parametrize(
+    "load_encoding",
+    [openai_public.cl100k_base, openai_public.o200k_base, openai_public.p50k_base],
+    ids=["cl100k_base", "o200k_base", "p50k_base"],
+)
+def test_bundled_tiktoken_cache_loads_without_the_network(load_encoding, tmp_path, monkeypatch):
+    cache_copy = tmp_path / "tokenizers"
+    shutil.copytree(_tokenizers_dir_without_importing_litellm(), cache_copy)
+    monkeypatch.setenv("TIKTOKEN_CACHE_DIR", str(cache_copy))
+
+    def refuse_download(url):
+        raise AssertionError(f"tiktoken rejected the bundled cache and tried to download {url}")
+
+    monkeypatch.setattr(tiktoken.load, "read_file", refuse_download)
+
+    assert load_encoding()["mergeable_ranks"]
+
+
+def test_gitattributes_keeps_the_bundled_caches_byte_exact():
+    caches = sorted(
+        (TOKENIZERS / p.name).as_posix()
+        for p in (REPO_ROOT / TOKENIZERS).iterdir()
+        if TIKTOKEN_CACHE_FILE_NAME.fullmatch(p.name)
+    )
+    assert caches, f"no tiktoken cache files in {REPO_ROOT / TOKENIZERS}"
+    try:
+        out = subprocess.run(
+            ["git", "check-attr", "text", "--", *caches],
+            cwd=REPO_ROOT,
+            capture_output=True,
+            text=True,
+            check=True,
+        ).stdout
+    except (OSError, subprocess.CalledProcessError):
+        pytest.skip("not a git checkout")
+
+    assert out.splitlines() == [f"{cache}: text: unset" for cache in caches]