diff --git a/.pre-commit-config.yaml b/.pre-commit-config.yaml
index db7321b93..33460222e 100644
--- a/.pre-commit-config.yaml
+++ b/.pre-commit-config.yaml
@@ -143,6 +143,11 @@ repos:
     name: Check attention backend documentation is up to date
     entry: python tools/pre_commit/generate_attention_backend_docs.py --check
     language: python
+  - id: check-boolean-context-manager
+    name: Check for boolean ops in with-statements
+    entry: python tools/pre_commit/check_boolean_context_manager.py
+    language: python
+    types: [python]
   # Keep `suggestion` last
   - id: suggestion
     name: Suggestion
diff --git a/tools/pre_commit/check_boolean_context_manager.py b/tools/pre_commit/check_boolean_context_manager.py
new file mode 100644
index 000000000..a482451ba
--- /dev/null
+++ b/tools/pre_commit/check_boolean_context_manager.py
@@ -0,0 +1,70 @@
+# SPDX-License-Identifier: Apache-2.0
+# SPDX-FileCopyrightText: Copyright contributors to the vLLM project
+"""Lint: detect `with a() and b():` (boolean op in with-statement context).
+
+Using `and`/`or` to combine context managers is almost always a bug:
+
+    with ctx_a() and ctx_b():   # BUG: only ctx_b is entered
+    with ctx_a() or  ctx_b():   # BUG: only ctx_a is entered
+
+The correct way to combine context managers is:
+
+    with ctx_a(), ctx_b():          # comma-separated
+    with (ctx_a(), ctx_b()):        # parenthesized (Python 3.10+)
+    with contextlib.ExitStack() ... # ExitStack
+"""
+
+import ast
+import sys
+
+
+def check_file(filepath: str) -> list[str]:
+    try:
+        with open(filepath, encoding="utf-8") as f:
+            source = f.read()
+    except (OSError, UnicodeDecodeError):
+        return []
+
+    try:
+        tree = ast.parse(source, filename=filepath)
+    except SyntaxError:
+        return []
+
+    violations = []
+    for node in ast.walk(tree):
+        if isinstance(node, (ast.With, ast.AsyncWith)):
+            for item in node.items:
+                if isinstance(item.context_expr, ast.BoolOp):
+                    op = "and" if isinstance(item.context_expr.op, ast.And) else "or"
+                    violations.append(
+                        f"{filepath}:{item.context_expr.lineno}: "
+                        f"boolean `{op}` used to combine context managers "
+                        f"in `with` statement — use a comma instead"
+                    )
+    return violations
+
+
+def main() -> int:
+    if len(sys.argv) < 2:
+        print("Usage: check_boolean_context_manager.py <file> ...", file=sys.stderr)
+        return 1
+
+    all_violations = []
+    for filepath in sys.argv[1:]:
+        all_violations.extend(check_file(filepath))
+
+    if all_violations:
+        print(
+            "❌ Boolean operator used to combine context managers in `with` "
+            "statement.\n"
+            "   `with a() and b():` only enters `b()` as a context manager.\n"
+            "   Use `with a(), b():` or `with (a(), b()):` instead.\n"
+        )
+        for v in all_violations:
+            print(f"  {v}")
+        return 1
+    return 0
+
+
+if __name__ == "__main__":
+    sys.exit(main())