diff --git a/Makefile.pre.in b/Makefile.pre.in
index 4f2465798db820..bc82e9a58a795d 100644
--- a/Makefile.pre.in
+++ b/Makefile.pre.in
@@ -127,7 +127,7 @@ PY_CORE_CFLAGS=	$(PY_STDMODULE_CFLAGS) -DPy_BUILD_CORE
 # LDFLAGS used to build executables and shared targets.
 PY_CORE_LDFLAGS=$(PY_LDFLAGS) $(PY_LDFLAGS_NODIST)
 CONFIGURE_EXE_LDFLAGS=@EXE_LDFLAGS@
-PY_CORE_EXE_LDFLAGS:= $(if $(CONFIGURE_EXE_LDFLAGS), $(CONFIGURE_EXE_LDFLAGS) $(PY_LDFLAGS_NODIST), $(PY_CORE_LDFLAGS))
+PY_CORE_EXE_LDFLAGS= $(if $(CONFIGURE_EXE_LDFLAGS), $(CONFIGURE_EXE_LDFLAGS) $(PY_LDFLAGS_NODIST), $(PY_CORE_LDFLAGS))
 # Strict or non-strict aliasing flags used to compile dtoa.c, see above
 CFLAGS_ALIASING=@CFLAGS_ALIASING@
 # Compilation flags only for ceval.c.
diff --git a/Misc/NEWS.d/next/Build/2026-07-11-01-53-58.gh-issue-153285.YmSox4.rst b/Misc/NEWS.d/next/Build/2026-07-11-01-53-58.gh-issue-153285.YmSox4.rst
new file mode 100644
index 00000000000000..e4b528fc2b2e1f
--- /dev/null
+++ b/Misc/NEWS.d/next/Build/2026-07-11-01-53-58.gh-issue-153285.YmSox4.rst
@@ -0,0 +1,2 @@
+Fix a build failure with ``--with-lto`` on macOS where executable linker
+flags expanded Make's ``$@`` before the target was known.