diff --git a/src/lighteval/models/sglang/sglang_model.py b/src/lighteval/models/sglang/sglang_model.py
index e5c0f4d87..eaa9a4121 100644
--- a/src/lighteval/models/sglang/sglang_model.py
+++ b/src/lighteval/models/sglang/sglang_model.py
@@ -268,7 +268,10 @@ def _greedy_until(
             # should have been managed by the prompt creator/few shot manager if requested by the user.
 
             inputs = tokenized["input_ids"]
-            context_size = len(inputs[0])
+            # Use the longest prompt in the batch (worst case) for truncation decisions,
+            # not only the first item, otherwise shorter first samples can skip truncation
+            # while longer later samples still exceed max_length.
+            context_size = max((len(input_ids) for input_ids in inputs), default=0)
 
             # left truncate the inputs to the maximum length
             if max_new_tokens is not None:
diff --git a/tests/unit/models/sglang/test_sglang_model.py b/tests/unit/models/sglang/test_sglang_model.py
new file mode 100644
index 000000000..5824c6fbc
--- /dev/null
+++ b/tests/unit/models/sglang/test_sglang_model.py
@@ -0,0 +1,87 @@
+# MIT License
+
+# Copyright (c) 2025 The HuggingFace Team
+
+# Permission is hereby granted, free of charge, to any person obtaining a copy
+# of this software and associated documentation files (the "Software"), to deal
+# in the Software without restriction, including without limitation the rights
+# to use, copy, modify, merge, publish, distribute, sublicense, and/or sell
+# copies of the Software, and to permit persons to whom the Software is
+# furnished to do so, subject to the following conditions:
+
+# The above copyright notice and this permission notice shall be included in all
+# copies or substantial portions of the Software.
+
+# THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF ANY KIND, EXPRESS OR
+# IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF MERCHANTABILITY,
+# FITNESS FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT SHALL THE
+# AUTHORS OR COPYRIGHT HOLDERS BE LIABLE FOR ANY CLAIM, DAMAGES OR OTHER
+# LIABILITY, WHETHER IN AN ACTION OF CONTRACT, TORT OR OTHERWISE, ARISING FROM,
+# OUT OF OR IN CONNECTION WITH THE SOFTWARE OR THE USE OR OTHER DEALINGS IN THE
+# SOFTWARE.
+
+import unittest
+from unittest.mock import Mock
+
+from lighteval.models.sglang.sglang_model import SGLangModel
+from lighteval.tasks.requests import Doc
+
+
+class FakeTokenizer:
+    """Maps each context to a token list whose length is unrelated to its character length."""
+
+    def __init__(self, token_lengths_by_prefix: dict):
+        self.token_lengths_by_prefix = token_lengths_by_prefix
+
+    def __call__(self, contexts, add_special_tokens=True):
+        input_ids = [[1] * self.token_lengths_by_prefix[context[0]] for context in contexts]
+        return {"input_ids": input_ids}
+
+
+class TestSGLangGreedyUntilTruncation(unittest.TestCase):
+    def test_truncation_uses_longest_tokenized_input_in_batch(self):
+        """The batch is sorted by CHARACTER length, so inputs[0] is not necessarily the
+        longest in TOKENS. Truncation must be sized from the longest tokenized input,
+        otherwise a shorter-in-characters but longer-in-tokens prompt is sent to the
+        engine above max_length. Same bug class as the vllm one reported in #1204."""
+        max_length = 50
+        max_new_tokens = 10
+
+        model = SGLangModel.__new__(SGLangModel)
+        model._max_length = max_length
+        model._add_special_tokens = False
+        model.use_chat_template = False
+        model.prompt_manager = Mock(prepare_prompt=lambda doc: doc.query)
+        # "a..." prompts: many characters, few tokens. "b..." prompts: fewer characters,
+        # many tokens (e.g. CJK text). The "a" doc sorts first by character length.
+        model._tokenizer = FakeTokenizer({"a": 10, "b": 60})
+
+        generate_calls = []
+
+        def fake_generate(inputs, max_new_tokens=None, stop_tokens=None, num_samples=1):
+            generate_calls.append(inputs)
+            return [{"text": "out", "meta_info": {"output_token_logprobs": [(-0.5, 7)]}} for _ in inputs]
+
+        model._generate = fake_generate
+
+        docs = [
+            Doc(query="a" * 100, choices=[""], gold_index=0, generation_size=max_new_tokens),
+            Doc(query="b" * 90, choices=[""], gold_index=0, generation_size=max_new_tokens),
+        ]
+
+        responses = model._greedy_until(docs)
+
+        self.assertEqual(len(responses), 2)
+        self.assertTrue(generate_calls)
+        for inputs in generate_calls:
+            for input_ids in inputs:
+                self.assertLessEqual(
+                    len(input_ids) + max_new_tokens,
+                    max_length,
+                    f"an input of {len(input_ids)} tokens plus {max_new_tokens} new tokens "
+                    f"exceeds max_length={max_length}: truncation was sized from the wrong input",
+                )
+
+
+if __name__ == "__main__":
+    unittest.main()