diff --git a/pkgs/development/compilers/gcc/common/configure-flags.nix b/pkgs/development/compilers/gcc/common/configure-flags.nix
index aa8ecc62e55a..accd08088c28 100644
--- a/pkgs/development/compilers/gcc/common/configure-flags.nix
+++ b/pkgs/development/compilers/gcc/common/configure-flags.nix
@@ -244,6 +244,11 @@ let
     ++ lib.optionals (langD) [
       "--with-target-system-zlib=yes"
     ]
+    # Clang 11 performs an optimization on x86_64 that is sensitive to the presence of debug info.
+    # This causes GCC to fail to bootstrap due to object file differences between stages 2 and 3.
+    ++ lib.optionals (targetPlatform.isDarwin && targetPlatform.isx86_64) [
+      "--with-as=${targetPackages.darwin.cctools-port}/bin/${targetPrefix}as"
+    ]
   ;
 
 in configureFlags