diff --git a/tests/v1/structured_output/test_validation.py b/tests/v1/structured_output/test_validation.py
index 7ea60cc660..08be56613c 100644
--- a/tests/v1/structured_output/test_validation.py
+++ b/tests/v1/structured_output/test_validation.py
@@ -70,3 +70,36 @@ def test_degenerate_structured_outputs_rejected(structured_outputs, match):
             StructuredOutputsConfig(),
             tokenizer=object(),
         )
+
+
+@pytest.mark.parametrize(
+    "regex",
+    [
+        "\x00",  # a lone leading NUL
+        "\x00\x01\x02\x1f",  # a NUL followed by other control chars
+        "[0-9]\x00",  # an embedded NUL
+    ],
+)
+def test_regex_with_nul_byte_rejected(regex):
+    """A NUL byte is never meaningful in a structured-outputs regex and is not
+    handled by xgrammar's native regex converter. It must be rejected at request
+    validation in every backend mode (a clean 400), instead of reaching that
+    native code or silently falling back to another backend in the default
+    'auto' mode."""
+    params = SamplingParams(structured_outputs=StructuredOutputsParams(regex=regex))
+
+    # Rejected before backend selection, so it is a 400 even in 'auto' mode
+    # (which would otherwise catch the error and fall back to another backend).
+    with pytest.raises(VLLMValidationError, match="NUL"):
+        params._validate_structured_outputs(
+            _StubModelConfig(is_diffusion=False),
+            StructuredOutputsConfig(),
+            tokenizer=object(),
+        )
+
+    # The xgrammar backend also rejects it directly (defense in depth), before
+    # the pattern reaches the native from_regex call.
+    from vllm.v1.structured_output.backend_xgrammar import validate_xgrammar_grammar
+
+    with pytest.raises(ValueError, match="NUL"):
+        validate_xgrammar_grammar(params)
diff --git a/vllm/sampling_params.py b/vllm/sampling_params.py
index 816df226d8..46c4046082 100644
--- a/vllm/sampling_params.py
+++ b/vllm/sampling_params.py
@@ -1029,6 +1029,15 @@ class SamplingParams(
                 "structured_outputs.json_object must be True if set; omit "
                 "structured_outputs to disable structured outputs"
             )
+        # Reject a regex containing a NUL byte early, in every backend mode. A
+        # NUL is never meaningful in a regex pattern and is not handled by the
+        # regex-to-grammar conversion. Checked here, before backend selection,
+        # so it is a clean 400 rather than a silent fallback in the default
+        # "auto" mode.
+        if self.structured_outputs.regex and "\x00" in self.structured_outputs.regex:
+            raise VLLMValidationError(
+                "structured_outputs.regex must not contain a NUL character ('\\x00')"
+            )
 
         from vllm.v1.structured_output.backend_guidance import (
             has_guidance_unsupported_json_features,
diff --git a/vllm/v1/structured_output/backend_xgrammar.py b/vllm/v1/structured_output/backend_xgrammar.py
index 58b726bf72..e11b1601e1 100644
--- a/vllm/v1/structured_output/backend_xgrammar.py
+++ b/vllm/v1/structured_output/backend_xgrammar.py
@@ -284,6 +284,14 @@ def validate_xgrammar_grammar(sampling_params: SamplingParams) -> None:
     so_params = sampling_params.structured_outputs
 
     if so_params.regex:
+        # A NUL byte is never meaningful in a regex pattern and is not handled
+        # by xgrammar's native regex converter. Reject it here, before the
+        # pattern reaches that native code; the try/except below does not cover
+        # this case.
+        if "\x00" in so_params.regex:
+            raise ValueError(
+                "structured_outputs.regex must not contain a NUL character ('\\x00')"
+            )
         try:
             compile_regex_with_timeout(
                 xgr.Grammar.from_regex,