diff --git a/tests/test_request_input_bounds.py b/tests/test_request_input_bounds.py
index 395abe50c6..44f536e7fb 100644
--- a/tests/test_request_input_bounds.py
+++ b/tests/test_request_input_bounds.py
@@ -162,6 +162,40 @@ def test_bad_word_tokenization_limit_can_be_overridden(monkeypatch):
     assert tokenizer.calls == 3
 
 
+class EmptyBaseEncodingTokenizer:
+    max_token_id = 1024
+
+    def encode(self, text: str, add_special_tokens: bool = False) -> list[int]:
+        return [216] if text.startswith(" ") else []
+
+
+def test_bad_word_rejects_empty_base_tokenization():
+    params = SamplingParams(bad_words=["\x16"])
+
+    with pytest.raises(
+        VLLMValidationError,
+        match="must tokenize to at least one token",
+    ) as exc_info:
+        params.update_from_tokenizer(EmptyBaseEncodingTokenizer())
+
+    assert exc_info.value.parameter == "bad_words"
+
+
+class EmptyPrefixedEncodingTokenizer:
+    max_token_id = 1024
+
+    def encode(self, text: str, add_special_tokens: bool = False) -> list[int]:
+        return [] if text.startswith(" ") else [321]
+
+
+def test_bad_word_skips_empty_optional_prefixed_tokenization():
+    params = SamplingParams(bad_words=["word"])
+
+    params.update_from_tokenizer(EmptyPrefixedEncodingTokenizer())
+
+    assert params.bad_words_token_ids == [[321]]
+
+
 # --- Beam search: beam width / n honor the sequence cap --------------------
 
 
diff --git a/vllm/sampling_params.py b/vllm/sampling_params.py
index e4e203b103..7cf152fc7d 100644
--- a/vllm/sampling_params.py
+++ b/vllm/sampling_params.py
@@ -707,6 +707,17 @@ class SamplingParams(
                     text=prompt, add_special_tokens=False
                 )
 
+                if not prompt_token_ids:
+                    if not add_prefix_space:
+                        raise VLLMValidationError(
+                            "bad_words entries must tokenize to at least one token.",
+                            parameter="bad_words",
+                            value=self.bad_words,
+                        )
+                    # The unprefixed form is still enforceable when only the
+                    # optional space-prefixed form tokenizes to nothing.
+                    continue
+
                 # If no space at the beginning
                 # or if prefix space produces a new word token
                 if (not add_prefix_space) or (