diff --git a/tests/streaming/test_dataset.py b/tests/streaming/test_dataset.py
index f868a453..aafb509f 100644
--- a/tests/streaming/test_dataset.py
+++ b/tests/streaming/test_dataset.py
@@ -799,16 +799,22 @@ def _simple_preprocess(_):
         yield torch.randint(0, 100, size=(10,), dtype=torch.int64)
 
 
-def _get_simulated_s3_dataloader(tmpdir):
+def _get_simulated_s3_dataloader(cache_dir, data_dir):
     dataset = EmulateS3StreamingDataset(
-        input_dir=Dir(str(tmpdir / "s3cache"), str(tmpdir / "optimized")),
+        input_dir=Dir(cache_dir, data_dir),
         item_loader=TokensLoader(block_size=10),
     )
     return StreamingDataLoader(dataset, batch_size=2, num_workers=1)
 
 
+@pytest.mark.skipif(sys.platform == "win32", reason="Not tested on windows and MacOs")
 @mock.patch.dict(os.environ, {}, clear=True)
 def test_dataset_resume_on_future_chunks(tmpdir):
+    """This test is constructed to test resuming from a chunk past the first chunk, when
+    subsequent chunks don't have the same size."""
+    s3_cache_dir = str(tmpdir / "s3cache")
+    data_dir = str(tmpdir / "optimized")
+
     optimize(
         fn=_simple_preprocess,
         inputs=list(range(8)),
@@ -816,12 +822,12 @@ def test_dataset_resume_on_future_chunks(tmpdir):
         chunk_size=190,
         num_workers=4,
     )
-    assert len(os.listdir(tmpdir / "optimized")) == 9  # 8 chunks + 1 index file
+    assert len(os.listdir(tmpdir / "optimized")) > 1
 
-    os.mkdir(tmpdir / "s3cache")
-    shutil.rmtree("/cache/chunks", ignore_errors=True)  # TODO
+    os.mkdir(s3_cache_dir)
+    shutil.rmtree("/cache/chunks", ignore_errors=True)
 
-    train_dataloader = _get_simulated_s3_dataloader(tmpdir)
+    train_dataloader = _get_simulated_s3_dataloader(s3_cache_dir, data_dir)
     batches_to_fetch = 16
     batch_to_resume_from = None
     for i, batch in enumerate(train_dataloader):
@@ -831,11 +837,12 @@ def test_dataset_resume_on_future_chunks(tmpdir):
             batch_to_resume_from = batch
             break
 
-    shutil.rmtree(tmpdir / "s3cache")
-    os.mkdir(tmpdir / "s3cache")
+    shutil.rmtree(s3_cache_dir)
+    os.mkdir(s3_cache_dir)
     shutil.rmtree("/cache/chunks", ignore_errors=True)
-    train_dataloader = _get_simulated_s3_dataloader(tmpdir)
+    train_dataloader = _get_simulated_s3_dataloader(s3_cache_dir, data_dir)
     train_dataloader.load_state_dict(dataloader_state)
+    # The next batch after resuming must match what we should have gotten next in the initial loop
     assert torch.equal(next(iter(train_dataloader)), batch_to_resume_from)