I don't have macOS but a WAG will do.

# Rust tests and lints will be skipped. Delete if not intended.
[ci skip-rust]

# Building wheels and fs_util will be skipped. Delete if not intended.
[ci skip-build-wheels]

src/python/pants/backend/python/lint/black/rules.py

@@ -16,6 +16,7 @@
     PexRequirements,
     VenvPex,
     VenvPexProcess,
+    VenvPexRequest,
 )
 from pants.core.goals.fmt import FmtResult
 from pants.core.goals.lint import LintRequest, LintResult, LintResults
@@ -94,14 +95,18 @@ async def setup_black(
         else PexInterpreterConstraints(black.interpreter_constraints)
     )
 
+    black_script = "black"
     black_pex_request = Get(
         VenvPex,
-        PexRequest(
-            output_filename="black.pex",
-            internal_only=True,
-            requirements=PexRequirements(black.all_requirements),
-            interpreter_constraints=tool_interpreter_constraints,
-            entry_point=black.entry_point,
+        VenvPexRequest(
+            bin_names=[black_script],
+            pex_request=PexRequest(
+                output_filename="black.pex",
+                internal_only=True,
+                requirements=PexRequirements(black.all_requirements),
+                interpreter_constraints=tool_interpreter_constraints,
+                entry_point=black.entry_point,
+            ),
         ),
     )
 
@@ -134,6 +139,7 @@ async def setup_black(
         Process,
         VenvPexProcess(
             black_pex,
+            script=black_pex.bin[black_script],
             argv=generate_args(
                 source_files=source_files, black=black, check_only=setup_request.check_only
             ),

src/python/pants/backend/python/util_rules/pex.py

@@ -927,6 +927,7 @@ class VenvPexProcess:
     argv: Tuple[str, ...]
     description: str = dataclasses.field(compare=False)
     level: LogLevel
+    script: Optional[Script]
     input_digest: Optional[Digest]
     extra_env: Optional[FrozenDict[str, str]]
     output_files: Optional[Tuple[str, ...]]
@@ -942,6 +943,7 @@ def __init__(
         description: str,
         argv: Iterable[str] = (),
         level: LogLevel = LogLevel.INFO,
+        script: Optional[Script] = None,
         input_digest: Optional[Digest] = None,
         extra_env: Optional[Mapping[str, str]] = None,
         output_files: Optional[Iterable[str]] = None,
@@ -954,6 +956,7 @@ def __init__(
         self.argv = tuple(argv)
         self.description = description
         self.level = level
+        self.script = script
         self.input_digest = input_digest
         self.extra_env = FrozenDict(extra_env) if extra_env else None
         self.output_files = tuple(output_files) if output_files else None
@@ -966,7 +969,7 @@ def __init__(
 @rule
 async def setup_venv_pex_process(request: VenvPexProcess) -> Process:
     venv_pex = request.venv_pex
-    argv = (venv_pex.pex.argv0, *request.argv)
+    argv = (request.script.argv0 if request.script else venv_pex.pex.argv0, *request.argv)
     input_digest = (
         await Get(Digest, MergeDigests((venv_pex.digest, request.input_digest)))
         if request.input_digest