diff --git a/src/black/__init__.py b/src/black/__init__.py
index f9f1b51c6fa..eb5d6e40892 100644
--- a/src/black/__init__.py
+++ b/src/black/__init__.py
@@ -66,6 +66,7 @@
 from black.parsing import (  # noqa F401
     ASTSafetyError,
     InvalidInput,
+    SourceASTParseError,
     lib2to3_parse,
     parse_ast,
     stringify_ast,
@@ -1086,6 +1087,8 @@ def check_stability_and_equivalence(
     """
     try:
         assert_equivalent(src_contents, dst_contents)
+    except SourceASTParseError:
+        raise
     except ASTSafetyError:
         if _target_versions_exceed_runtime(mode.target_versions):
             raise ASTSafetyError(
@@ -1632,7 +1635,7 @@ def assert_equivalent(src: str, dst: str) -> None:
     try:
         src_ast = parse_ast(src)
     except Exception as exc:
-        raise ASTSafetyError(
+        raise SourceASTParseError(
             "cannot use --safe with this file; failed to parse source file AST: "
             f"{exc}\n"
             "This could be caused by running Black with an older Python version "
diff --git a/src/black/parsing.py b/src/black/parsing.py
index cb4f715dcb3..5dc234c911a 100644
--- a/src/black/parsing.py
+++ b/src/black/parsing.py
@@ -106,6 +106,15 @@ class ASTSafetyError(Exception):
     """Raised when Black's generated code is not equivalent to the old AST."""
 
 
+class SourceASTParseError(Exception):
+    """Raised when the source file cannot be parsed by ast.parse().
+
+    This is not a bug in Black — Black's lib2to3-based parser is more lenient
+    than Python's ast.parse(), so it may accept code that ast.parse() rejects.
+    In blackd, this should be reported as a 400 Bad Request.
+    """
+
+
 def _parse_single_version(
     src: str, version: tuple[int, int], *, type_comments: bool
 ) -> ast.AST:
diff --git a/src/blackd/__init__.py b/src/blackd/__init__.py
index 4646e919735..5df160b6b7b 100644
--- a/src/blackd/__init__.py
+++ b/src/blackd/__init__.py
@@ -206,6 +206,8 @@ async def handle(
         return web.Response(status=204, headers=headers)
     except black.InvalidInput as e:
         return web.Response(status=400, headers=headers, text=str(e))
+    except black.SourceASTParseError as e:
+        return web.Response(status=400, headers=headers, text=str(e))
     except web.HTTPException:
         raise
     except Exception as e: