diff --git a/spec/compiler/parser/to_s_spec.cr b/spec/compiler/parser/to_s_spec.cr
index 63da166aba45..f1af8d9cb586 100644
--- a/spec/compiler/parser/to_s_spec.cr
+++ b/spec/compiler/parser/to_s_spec.cr
@@ -108,8 +108,18 @@ describe "ASTNode#to_s" do
   expect_to_s "def foo(x, @[Foo] **args)\nend"
   expect_to_s "def foo(x, **args, &block)\nend"
   expect_to_s "def foo(@[Foo] x, @[Bar] **args, @[Baz] &block)\nend"
-  expect_to_s "def foo(x, **args, &block : (_ -> _))\nend"
-  expect_to_s "def foo(& : (->))\nend"
+
+  # 14216
+  expect_to_s "def foo(x, **args, &block : _ -> _)\nend"
+  expect_to_s "def foo(x, **args, &block : (_ -> _))\nend", "def foo(x, **args, &block : _ -> _)\nend"
+  expect_to_s "def foo(& : ->)\nend"
+  expect_to_s "def foo(& : (->))\nend", "def foo(& : ->)\nend"
+  expect_to_s "def foo(x : (T -> U) -> V, *args : (T -> U) -> V, y : (T -> U) -> V, **opts : (T -> U) -> V, & : (T -> U) -> V) : ((T -> U) -> V)\nend"
+  expect_to_s "foo(x : (T -> U) -> V, W)"
+  expect_to_s "foo[x : (T -> U) -> V, W]"
+  expect_to_s "foo[x : (T -> U) -> V, W] = 1"
+  expect_to_s "lib LibFoo\n  fun foo(x : (T -> U) -> V, W) : ((T -> U) -> V)\nend"
+
   expect_to_s "macro foo(@[Foo] id)\nend"
   expect_to_s "macro foo(**args)\nend"
   expect_to_s "macro foo(@[Foo] **args)\nend"
diff --git a/src/compiler/crystal/syntax/to_s.cr b/src/compiler/crystal/syntax/to_s.cr
index 7735cddb3951..58c553ea18e6 100644
--- a/src/compiler/crystal/syntax/to_s.cr
+++ b/src/compiler/crystal/syntax/to_s.cr
@@ -18,6 +18,13 @@ module Crystal
     @macro_expansion_pragmas : Hash(Int32, Array(Lexer::LocPragma))?
     @current_arg_type : DefArgType = :none
 
+    # Inside a comma-separated list of parameters or args, this becomes true and
+    # the outermost pair of parentheses are removed from type restrictions that
+    # are `ProcNotation` nodes, so `foo(x : (T, U -> V), W)` becomes
+    # `foo(x : T, U -> V, W)`. This is used by defs, lib funs, and calls to deal
+    # with the parsing rules for `->`. See #11966 and #14216 for more details.
+    getter? drop_parens_for_proc_notation = false
+
     private enum DefArgType
       NONE
       SPLAT
@@ -436,24 +443,26 @@ module Crystal
 
     private def visit_args(node, exclude_last = false)
       printed_arg = false
-      node.args.each_with_index do |arg, i|
-        break if exclude_last && i == node.args.size - 1
+      drop_parens_for_proc_notation do
+        node.args.each_with_index do |arg, i|
+          break if exclude_last && i == node.args.size - 1
 
-        @str << ", " if printed_arg
-        arg.accept self
-        printed_arg = true
-      end
-      if named_args = node.named_args
-        named_args.each do |named_arg|
           @str << ", " if printed_arg
-          named_arg.accept self
+          arg.accept self
           printed_arg = true
         end
-      end
-      if block_arg = node.block_arg
-        @str << ", " if printed_arg
-        @str << '&'
-        block_arg.accept self
+        if named_args = node.named_args
+          named_args.each do |named_arg|
+            @str << ", " if printed_arg
+            named_arg.accept self
+            printed_arg = true
+          end
+        end
+        if block_arg = node.block_arg
+          @str << ", " if printed_arg
+          @str << '&'
+          block_arg.accept self
+        end
       end
     end
 
@@ -632,25 +641,27 @@ module Crystal
       if node.args.size > 0 || node.block_arity || node.double_splat
         @str << '('
         printed_arg = false
-        node.args.each_with_index do |arg, i|
-          @str << ", " if printed_arg
-          @current_arg_type = :splat if node.splat_index == i
-          arg.accept self
-          printed_arg = true
-        end
-        if double_splat = node.double_splat
-          @current_arg_type = :double_splat
-          @str << ", " if printed_arg
-          double_splat.accept self
-          printed_arg = true
-        end
-        if block_arg = node.block_arg
-          @current_arg_type = :block_arg
-          @str << ", " if printed_arg
-          block_arg.accept self
-        elsif node.block_arity
-          @str << ", " if printed_arg
-          @str << '&'
+        drop_parens_for_proc_notation do
+          node.args.each_with_index do |arg, i|
+            @str << ", " if printed_arg
+            @current_arg_type = :splat if node.splat_index == i
+            arg.accept self
+            printed_arg = true
+          end
+          if double_splat = node.double_splat
+            @current_arg_type = :double_splat
+            @str << ", " if printed_arg
+            double_splat.accept self
+            printed_arg = true
+          end
+          if block_arg = node.block_arg
+            @current_arg_type = :block_arg
+            @str << ", " if printed_arg
+            block_arg.accept self
+          elsif node.block_arity
+            @str << ", " if printed_arg
+            @str << '&'
+          end
         end
         @str << ')'
       end
@@ -680,6 +691,8 @@ module Crystal
       if node.args.size > 0 || node.block_arg || node.double_splat
         @str << '('
         printed_arg = false
+        # NOTE: `drop_parens_for_proc_notation` needed here if macros support
+        # restrictions
         node.args.each_with_index do |arg, i|
           @str << ", " if printed_arg
           @current_arg_type = :splat if i == node.splat_index
@@ -830,17 +843,24 @@ module Crystal
     end
 
     def visit(node : ProcNotation)
-      @str << '('
-      if inputs = node.inputs
-        inputs.join(@str, ", ", &.accept self)
-        @str << ' '
-      end
-      @str << "->"
-      if output = node.output
-        @str << ' '
-        output.accept self
+      @str << '(' unless drop_parens_for_proc_notation?
+
+      # only drop the outermost pair of parentheses; this produces
+      # `foo(x : (T -> U) -> V, W)`, not
+      # `foo(x : ((T -> U) -> V), W)` nor `foo(x : T -> U -> V, W)`
+      drop_parens_for_proc_notation(false) do
+        if inputs = node.inputs
+          inputs.join(@str, ", ", &.accept self)
+          @str << ' '
+        end
+        @str << "->"
+        if output = node.output
+          @str << ' '
+          output.accept self
+        end
       end
-      @str << ')'
+
+      @str << ')' unless drop_parens_for_proc_notation?
       false
     end
 
@@ -1143,14 +1163,16 @@ module Crystal
       end
       if node.args.size > 0
         @str << '('
-        node.args.join(@str, ", ") do |arg|
-          if arg_name = arg.name.presence
-            @str << arg_name << " : "
+        drop_parens_for_proc_notation do
+          node.args.join(@str, ", ") do |arg|
+            if arg_name = arg.name.presence
+              @str << arg_name << " : "
+            end
+            arg.restriction.not_nil!.accept self
+          end
+          if node.varargs?
+            @str << ", ..."
           end
-          arg.restriction.not_nil!.accept self
-        end
-        if node.varargs?
-          @str << ", ..."
         end
         @str << ')'
       elsif node.varargs?
@@ -1575,6 +1597,16 @@ module Crystal
       @inside_macro = old_inside_macro
     end
 
+    def drop_parens_for_proc_notation(drop : Bool = true, &)
+      old_drop_parens_for_proc_notation = @drop_parens_for_proc_notation
+      @drop_parens_for_proc_notation = drop
+      begin
+        yield
+      ensure
+        @drop_parens_for_proc_notation = old_drop_parens_for_proc_notation
+      end
+    end
+
     def to_s : String
       @str.to_s
     end