diff --git a/lib/spitfire.ex b/lib/spitfire.ex
index be54d5c..d28c027 100644
--- a/lib/spitfire.ex
+++ b/lib/spitfire.ex
@@ -1283,52 +1283,149 @@ defmodule Spitfire do
                 meta
             end
 
-          lhs =
-            case lhs do
-              {:__block__, _, []} ->
-                []
+          {lhs, parser} = normalize_stab_lhs(lhs, parser)
 
-              {:__block__, [{:parens, _} | _], [[{key, _} | _] = kw]} when is_atom(key) ->
-                [kw]
+          ast =
+            {token, meta, [lhs, rhs]}
 
-              {:__block__, [{:parens, _} | _], [[{{_, _, _}, _} | _] = kw]} ->
-                [kw]
+          parser = Map.put(parser, :nesting, old_nesting)
 
-              {:comma, _, lhs} ->
-                lhs
+          {ast, eat_eoe(parser)}
+      end
+    end
+  end
 
-              {:when, [{:parens, _} | when_meta], when_args} ->
-                [{:when, when_meta, when_args}]
+  # Normalize stab clause LHS forms into the shape expected by `->` construction.
+  # When parsing fn heads, this also performs grammar-level validation for
+  # disallowed nested parentheses while keeping recoverable AST output.
+  defp normalize_stab_lhs(lhs, parser) do
+    in_fn_head_context? = Map.get(parser, :fn_head_context?, false)
 
-              {:__block__, [{:parens, _} = paren_meta | _], exprs} ->
-                case exprs do
-                  [[{key, _} | _] = kw] when is_atom(key) ->
-                    [{:__block__, [paren_meta], [kw]}]
+    case lhs do
+      {:__block__, _, []} ->
+        {[], parser}
 
-                  [[{{_, _, _}, _} | _] = kw] ->
-                    [{:__block__, [paren_meta], [kw]}]
+      {:comma, comma_meta, comma_args} ->
+        parser =
+          if in_fn_head_context? do
+            parser
+            |> maybe_error_nested_top_parens(comma_meta)
+            |> maybe_error_invalid_fn_head_args(comma_args)
+          else
+            parser
+          end
 
-                  [expr] ->
-                    [{:__block__, [paren_meta], [expr]}]
+        {comma_args, parser}
 
-                  _ ->
-                    lhs
-                end
+      {:when, [{:parens, _} | when_meta], when_args} ->
+        {[{:when, when_meta, when_args}], parser}
 
-              lhs ->
-                [lhs]
-            end
+      {:__block__, [{:parens, _} = paren_meta | _], exprs} ->
+        case {parenthesized_kw_head(lhs), exprs} do
+          {{:ok, block_meta, _paren_meta, kw}, _} ->
+            parser =
+              if in_fn_head_context? do
+                maybe_error_nested_top_parens(parser, block_meta)
+              else
+                parser
+              end
 
-          ast =
-            {token, meta, [lhs, rhs]}
+            {[kw], parser}
 
-          parser = Map.put(parser, :nesting, old_nesting)
+          {:error, [expr]} ->
+            {[{:__block__, [paren_meta], [expr]}], parser}
 
-          {ast, eat_eoe(parser)}
+          {:error, _} ->
+            {lhs, parser}
+        end
+
+      lhs ->
+        {[lhs], parser}
+    end
+  end
+
+  # In fn-head context, only certain LHS shapes should lower `when` precedence.
+  # This allows `<-` and `\\` to be consumed by the guard expression when the
+  # head is explicitly grouped (empty parens, parenthesized comma args, or
+  # parenthesized keyword heads).
+  defp fn_head_simple_for_when_precedence?(lhs) do
+    match?({:__block__, _, []}, lhs) or
+      match?({:comma, [{:parens, _} | _], _}, lhs) or
+      match?({:ok, _block_meta, _paren_meta, _kw}, parenthesized_kw_head(lhs))
+  end
+
+  # Validate raw fn-head LHS before `when` normalization can flatten argument
+  # structure and hide nested-parens evidence.
+  defp maybe_error_invalid_fn_head_lhs(parser, lhs) do
+    case lhs do
+      {:comma, comma_meta, comma_args} ->
+        parser
+        |> maybe_error_nested_top_parens(comma_meta)
+        |> maybe_error_invalid_fn_head_args(comma_args)
+
+      lhs ->
+        case parenthesized_kw_head(lhs) do
+          {:ok, block_meta, _paren_meta, _kw} ->
+            maybe_error_nested_top_parens(parser, block_meta)
+
+          :error ->
+            parser
+        end
+    end
+  end
+
+  # Reject nested grouped tuple/keyword arguments inside fn heads, for example
+  # `fn (a, (b, c)) -> ... end` and `fn ((a, b), c) -> ... end`.
+  defp maybe_error_invalid_fn_head_args(parser, args) when is_list(args) do
+    Enum.reduce(args, parser, fn arg, parser ->
+      case arg do
+        {:comma, [{:parens, parens_meta} | _], _} ->
+          put_error(parser, {nested_parens_error_meta(parens_meta), "unexpected parentheses"})
+
+        _ ->
+          case parenthesized_kw_head(arg) do
+            {:ok, _block_meta, {:parens, parens_meta}, _kw} ->
+              put_error(parser, {nested_parens_error_meta(parens_meta), "unexpected parentheses"})
+
+            :error ->
+              parser
+          end
       end
+    end)
+  end
+
+  defp maybe_error_invalid_fn_head_args(parser, _args), do: parser
+
+  # Reject top-level fn-head wrappers that carry more than one parens entry,
+  # such as `((a, b))` and `((a: 1))`.
+  defp maybe_error_nested_top_parens(parser, meta) do
+    case Enum.at(Keyword.get_values(meta, :parens), 1) do
+      nil ->
+        parser
+
+      inner_parens ->
+        put_error(parser, {nested_parens_error_meta(inner_parens), "unexpected parentheses"})
     end
   end
 
+  # Prefer the closing paren location when available to match parser diagnostics.
+  defp nested_parens_error_meta(parens_meta) do
+    Keyword.take(parens_meta[:closing] || parens_meta, [:line, :column])
+  end
+
+  # Extract parenthesized keyword-list heads like `(a: 1)` or `('x': 1)` from
+  # grouped AST nodes so fn-head normalization can preserve paren metadata.
+  defp parenthesized_kw_head({:__block__, [{:parens, _} = paren_meta | _] = block_meta, [[{key, _} | _] = kw]})
+       when is_atom(key) do
+    {:ok, block_meta, paren_meta, kw}
+  end
+
+  defp parenthesized_kw_head({:__block__, [{:parens, _} = paren_meta | _] = block_meta, [[{{_, _, _}, _} | _] = kw]}) do
+    {:ok, block_meta, paren_meta, kw}
+  end
+
+  defp parenthesized_kw_head(_), do: :error
+
   # Widen stab_state when outer expression is more complete than when `->` was first detected.
   defp maybe_widen_stab_state(parser, ast) do
     case {Map.get(parser, :stab_state), ast} do
@@ -1396,11 +1493,17 @@ defmodule Spitfire do
       # e.g., `() when bar 1, 2, 3 -> foo()` should parse `bar 1, 2, 3` as the guard
       {rhs, parser} =
         if token == :when do
-          # Check if when has simple LHS (empty block or comma args).
+          # Check if when has simple LHS (empty block or parenthesized comma args).
           # If so and we're in fn context, use lower precedence to allow <- in guard.
-          in_fn_context = Map.get(parser, :stop_before_stab_op?, false)
-          simple_lhs = match?({:__block__, _, []}, lhs) or match?({:comma, _, _}, lhs)
-          when_precedence = if in_fn_context and simple_lhs, do: @list_comma, else: effective_precedence
+          # For bare comma args (no parens), keep normal precedence so `<-` and
+          # `\\` bind to the trailing head argument instead of becoming part of
+          # the `when` guard.
+          # Also validate the raw fn-head lhs here before `when` flattening.
+          in_fn_context = Map.get(parser, :fn_head_context?, false)
+          parser = if in_fn_context, do: maybe_error_invalid_fn_head_lhs(parser, lhs), else: parser
+
+          when_precedence =
+            if in_fn_context and fn_head_simple_for_when_precedence?(lhs), do: @list_comma, else: effective_precedence
 
           {rhs, parser} =
             with_context(parser, %{stop_before_stab_op?: true}, fn parser ->
@@ -1448,14 +1551,6 @@ defmodule Spitfire do
                 # Empty block without parens
                 {token, newlines ++ meta, [rhs]}
 
-              {:__block__, [{:parens, _} = paren_meta | _], [[{key, _} | _] = kw]} when is_atom(key) ->
-                # (a: 1) when ... - preserve parens meta for stab
-                {token, [paren_meta | newlines ++ meta], [kw, rhs]}
-
-              {:__block__, [{:parens, _} = paren_meta | _], [[{{_, _, _}, _} | _] = kw]} ->
-                # Parenthesized kw list with interpolated key
-                {token, [paren_meta | newlines ++ meta], [kw, rhs]}
-
               {:comma, [{:parens, _} = paren_meta | _], args} ->
                 {token, [paren_meta | newlines ++ meta], args ++ [rhs]}
 
@@ -1463,11 +1558,30 @@ defmodule Spitfire do
                 {token, newlines ++ meta, args ++ [rhs]}
 
               _ ->
-                {token, newlines ++ meta, [lhs, rhs]}
+                case parenthesized_kw_head(lhs) do
+                  {:ok, _block_meta, paren_meta, kw} ->
+                    # (a: 1) when ... - preserve parens meta for stab
+                    {token, [paren_meta | newlines ++ meta], [kw, rhs]}
+
+                  :error ->
+                    {token, newlines ++ meta, [lhs, rhs]}
+                end
             end
 
           _ ->
-            {token, newlines ++ meta, [lhs, rhs]}
+            case lhs do
+              {:comma, comma_meta, args} when is_list(args) and args != [] ->
+                {leading, [last]} = Enum.split(args, -1)
+                {:comma, comma_meta, leading ++ [{token, newlines ++ meta, [last, rhs]}]}
+
+              {:when, when_meta, when_args} when is_list(when_args) and length(when_args) > 2 ->
+                {leading, [second_last, guard]} = Enum.split(when_args, -2)
+                when_node = {:when, when_meta, [second_last, guard]}
+                {:comma, [], leading ++ [{token, newlines ++ meta, [when_node, rhs]}]}
+
+              _ ->
+                {token, newlines ++ meta, [lhs, rhs]}
+            end
         end
 
       {ast, parser}
@@ -1491,7 +1605,8 @@ defmodule Spitfire do
            (unmatched_expr?(lhs) and rhs_has_bare_comma?(rhs_parser)) do
         # When the RHS of `|` has low-precedence operators (::, when, <-, \\) or
         # the LHS is an unmatched_expr (do-end) and the RHS has no-parens commas,
-        # treat `|` as a regular pipe operator (matching Elixir's LALR grammar).
+        # treat `|` as a regular infix operator so RHS parsing completes before
+        # map-update pair extraction.
         parse_infix_expression(parser, lhs)
       else
         {pairs, pairs_parser} = parse_map_update_pairs(rhs_parser)
@@ -2112,11 +2227,11 @@ defmodule Spitfire do
       newlines = get_newlines(parser)
       parser = parser |> next_token() |> eat_eoe()
 
-      # fn creates its own stab scope
+      # fn creates its own stab scope and enables fn-head specific validation.
       parser = Map.delete(parser, :stab_state)
 
       {exprs, parser} =
-        with_context(parser, %{stop_before_stab_op?: true}, fn parser ->
+        with_context(parser, %{stop_before_stab_op?: true, fn_head_context?: true}, fn parser ->
           while2 current_token(parser) not in [:end, :eof] <- parser do
             {ast, parser} =
               case Map.get(parser, :stab_state) do
diff --git a/test/spitfire_test.exs b/test/spitfire_test.exs
index 1dff579..68291b2 100644
--- a/test/spitfire_test.exs
+++ b/test/spitfire_test.exs
@@ -1483,6 +1483,42 @@ defmodule SpitfireTest do
       end
     end
 
+    test "fn args with parenthesized heads and low-precedence operators" do
+      codes = [
+        "fn a, u\\\\c -> :ok end",
+        "fn (a, 0<-c) -> :ok end",
+        "fn (a, b<-c<-d) -> :ok end",
+        "fn (a, b\\\\c\\\\d) -> :ok end",
+        "fn (a, b<-c) when is_integer(c) -> :ok end",
+        "fn (a, b\\\\c) when is_integer(c) -> :ok end",
+        "fn (a, b, d<-c) when is_integer(c) -> :ok end",
+        "fn (a, b, d\\\\c) when is_integer(c) -> :ok end",
+        "fn (a, b<-c) when c<-c -> :ok end",
+        "fn (a, b\\\\c) when c\\\\c -> :ok end",
+        "fn (a, b<-c<-d) when c<-c -> :ok end",
+        "fn (a, b\\\\c\\\\d) when c\\\\c -> :ok end",
+        "fn a, (b<-c) when c<-c -> :ok end",
+        "fn a, (b\\\\c) when c\\\\c -> :ok end",
+        "fn a, b<-c when c<-c -> :ok end",
+        "fn a, b\\\\c when c\\\\c -> :ok end",
+        "fn a, b when c<-c -> :ok end",
+        "fn a, b when c\\\\c -> :ok end",
+        "fn a, b when c<-c<-d -> :ok end",
+        "fn (a: 1) when c<-c -> :ok end",
+        "fn (a: 1) when c<-c<-d -> :ok end",
+        "fn (a: 1) when c\\\\c -> :ok end",
+        "fn (a: 1) when c\\\\c\\\\d -> :ok end",
+        "fn (x: 1, y: 2) when c<-c -> :ok end",
+        "fn (x: 1, y: 2) when c\\\\c -> :ok end",
+        "fn ('x': 1, y: 2) when c<-c -> :ok end",
+        "fn (x: 1, 'y': 2) when c\\\\c -> :ok end"
+      ]
+
+      for code <- codes do
+        assert Spitfire.parse(code) == s2q(code)
+      end
+    end
+
     test "capture operator" do
       codes = [
         ~s'''
@@ -2301,6 +2337,9 @@ defmodule SpitfireTest do
       assert Spitfire.parse("%e.(){}") == s2q("%e.(){}")
       assert Spitfire.parse("%e.(1){}") == s2q("%e.(1){}")
       assert Spitfire.parse("%e.(a, b){}") == s2q("%e.(a, b){}")
+
+      # Regression from absinthe-graphql/absinthe lexer
+      assert Spitfire.parse("comma = ascii_char([?,])") == s2q("comma = ascii_char([?,])")
     end
   end
 
@@ -2662,6 +2701,33 @@ defmodule SpitfireTest do
              }
     end
 
+    test "rejects nested parenthesized fn args" do
+      codes = [
+        # whole arg list double/triple-wrapped
+        "fn ((a, b)) -> :ok end",
+        "fn (((a, b))) -> :ok end",
+        "fn ((a, b)) when true -> :ok end",
+        "fn ((a, b<-c)) -> :ok end",
+        "fn ((a, b\\\\c)) -> :ok end",
+        "fn (((a, b<-c))) -> :ok end",
+        # keyword list double-wrapped
+        "fn ((a: 1)) -> :ok end",
+        "fn ((a: 1)) when true -> :ok end",
+        # individual args as parenthesized tuples
+        "fn ((a, b), c) -> :ok end",
+        "fn (a, (b, c)) -> :ok end",
+        "fn ((a, b), (c, d)) -> :ok end",
+        "fn ((a, b), (c, d)) when true -> :ok end",
+        "fn ((a, (b<-c))) -> :ok end",
+        "fn ((a, (b\\\\c))) -> :ok end"
+      ]
+
+      for code <- codes do
+        assert {:error, _} = s2q(code)
+        assert {:error, _, _} = Spitfire.parse(code)
+      end
+    end
+
     test "example from github issue" do
       code = ~S'''
       defmodule Foo do