diff --git a/src/lighteval/models/transformers/transformers_model.py b/src/lighteval/models/transformers/transformers_model.py
index 64e790a2f..94c117b67 100644
--- a/src/lighteval/models/transformers/transformers_model.py
+++ b/src/lighteval/models/transformers/transformers_model.py
@@ -713,6 +713,18 @@ def _padded_greedy_until(
                     add_special_tokens=self.add_special_tokens,
                 ).to(self.device)
 
+                # `truncation="longest_first"` above drops the overflow of any context longer than
+                # `max_context_continuation_size_allowed`, so `tokenized` alone no longer tells us how many
+                # tokens each context holds. `contexts` holds strings, so `len(context)` is a character
+                # count and cannot be compared against a token count: re-tokenize without a cap to get the
+                # real token counts (`verbose=False` silences the tokenizer's over-long-input warning).
+                context_token_counts = [
+                    len(input_ids)
+                    for input_ids in self.tokenizer(
+                        contexts, add_special_tokens=self.add_special_tokens, verbose=False
+                    )["input_ids"]
+                ]
+
                 # The main question for this step is the following:
                 # Would we rather truncate the prompt to allow generation to go to max_new_tokens, at the risk
                 # of losing some meaning, or have some generations that are exceedingly short?
@@ -739,7 +751,10 @@ def _padded_greedy_until(
                     input_ids=tokenized["input_ids"],
                     input_lengths=[len(item == 1) for item in tokenized["attention_mask"]],
                     input_mask=tokenized["attention_mask"],
-                    truncated=[max(len(c) - tokenized["input_ids"].shape[1], 0) for c in contexts],
+                    truncated=[
+                        max(context_token_count - tokenized["input_ids"].shape[1], 0)
+                        for context_token_count in context_token_counts
+                    ],
                     padded=[sum(mask == 0) for mask in tokenized["attention_mask"]],
                 )
 
diff --git a/tests/unit/models/test_transformers_model.py b/tests/unit/models/test_transformers_model.py
index da7c925ae..690e0804e 100644
--- a/tests/unit/models/test_transformers_model.py
+++ b/tests/unit/models/test_transformers_model.py
@@ -426,5 +426,49 @@ def test_transformers_model_use_chat_template_with_different_model_names(
                 self.assertEqual(model.use_chat_template, model._tokenizer.chat_template is not None)
 
 
+class TestTransformersModelTruncatedTokensCount(unittest.TestCase):
+    """`truncated_tokens_count` must count tokens, not `len(context) - token_count`."""
+
+    @patch("lighteval.models.transformers.transformers_model.Accelerator")
+    def setUp(self, mock_accelerator):
+        """Set up shared model instance for all tests."""
+        mock_accelerator_instance = Mock()
+        mock_accelerator_instance.device = torch.device("cpu")
+        mock_accelerator_instance.is_main_process = True
+        mock_accelerator_instance.prepare = lambda x: x
+        mock_accelerator_instance.gather = lambda x: x
+        mock_accelerator_instance.gather_for_metrics = lambda x: x
+        mock_accelerator.return_value = mock_accelerator_instance
+        # batch_size is set explicitly so the model is not run to detect the largest batch size
+        self.model = TransformersModel(TransformersModelConfig(model_name="gpt2", batch_size=1))
+
+    def _truncated_for(self, query: str) -> list[int]:
+        """Runs _padded_greedy_until with generation stubbed out and returns Batch.truncated."""
+        doc = Doc(query=query, choices=[], gold_index=0, generation_size=4, stop_sequences=["Question:"])
+        captured = {}
+
+        def fake_generate(**kwargs):
+            captured["truncated"] = list(kwargs["batch"].truncated)
+            return [ModelResponse(text=["stub"], output_tokens=[[0]], input_tokens=[0])]
+
+        with patch("lighteval.models.transformers.transformers_model.DataLoader") as mock_dataloader:
+            mock_dataloader.return_value = [[doc]]
+            with patch.object(self.model, "_generate", side_effect=fake_generate):
+                self.model._padded_greedy_until([doc])
+
+        return captured["truncated"]
+
+    def test_context_fitting_the_context_window_is_not_reported_as_truncated(self):
+        query = "The capital of France is"
+        self.assertLess(len(self.model.tokenizer(query)["input_ids"]), self.model.max_length)
+        self.assertEqual(self._truncated_for(query), [0])
+
+    def test_truncated_tokens_count_matches_the_dropped_token_count(self):
+        query = "hello world " * 700
+        token_count = len(self.model.tokenizer(query)["input_ids"])
+        self.assertGreater(token_count, self.model.max_length)
+        self.assertEqual(self._truncated_for(query), [token_count - self.model.max_length])
+
+
 if __name__ == "__main__":
     unittest.main()