diff --git a/compiler/GHC/CmmToAsm.hs b/compiler/GHC/CmmToAsm.hs
index c0ac96fa799b3b94bb51997416ed2ca071d95492..94bdaa648b0ed32a31eecb3412854e1b071a588a 100644
--- a/compiler/GHC/CmmToAsm.hs
+++ b/compiler/GHC/CmmToAsm.hs
@@ -812,6 +812,19 @@ generateJumpTables ncgImpl xs = concatMap f xs
 -- -----------------------------------------------------------------------------
 -- Shortcut branches
 
+-- Note [No asm-shortcutting on Darwin]
+-- ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
+-- Asm-shortcutting may produce relative references to symbols defined in
+-- other compilation units. This is not something that MachO relocations
+-- support (see #21972). For this reason we disable the optimisation on Darwin.
+-- We do so in the backend without a warning since this flag is enabled by
+-- `-O2`.
+--
+-- Another way to address this issue would be to rather implement a
+-- PLT-relocatable jump-table strategy. However, this would only benefit Darwin
+-- and does not seem worth the effort as this optimisation generally doesn't
+-- offer terribly great benefits.
+
 shortcutBranches
         :: forall statics instr jumpDest. (Outputable jumpDest)
         => NCGConfig
@@ -822,6 +835,8 @@ shortcutBranches
 
 shortcutBranches config ncgImpl tops weights
   | ncgEnableShortcutting config
+    -- See Note [No asm-shortcutting on Darwin]
+  , not $ osMachOTarget $ platformOS $ ncgPlatform config
   = ( map (apply_mapping ncgImpl mapping) tops'
     , shortcutWeightMap mappingBid <$!> weights )
   | otherwise
diff --git a/docs/users_guide/using-optimisation.rst b/docs/users_guide/using-optimisation.rst
index d3ca68a1df4626044e00d0238f73c91028942f84..df87fdb6a3da716584f9a1db67d74a2e6535f63a 100644
--- a/docs/users_guide/using-optimisation.rst
+++ b/docs/users_guide/using-optimisation.rst
@@ -262,8 +262,10 @@ by saying ``-fno-wombat``.
     of a unconditionally jump, we replace all jumps to A by jumps to the successor
     of A.
 
-    This is mostly done during Cmm passes. However this can miss corner cases. So at -O2
-    we run the pass again at the asm stage to catch these.
+    This is mostly done during Cmm passes. However this can miss corner cases.
+    So at ``-O2`` this flag runs the pass again at the assembly stage to catch
+    these. Note that due to platform limitations (:ghc-ticket:`21972`) this flag
+    does nothing on macOS.
 
 .. ghc-flag:: -fblock-layout-cfg
     :shortdesc: Use the new cfg based block layout algorithm.