diff --git a/lib/elixir/lib/macro.ex b/lib/elixir/lib/macro.ex
index c3803470ff1..d012a499527 100644
--- a/lib/elixir/lib/macro.ex
+++ b/lib/elixir/lib/macro.ex
@@ -2674,6 +2674,75 @@ defmodule Macro do
     end
   end
 
+  defp dbg_ast_to_debuggable({:with, meta, args} = ast, _env) do
+    {opts, clauses} = List.pop_at(args, -1)
+    unmatched_ast_var = unique_var(:unmatched_ast, __MODULE__)
+    unmatched_else_var = unique_var(:unmatched_else, __MODULE__)
+    result_var = unique_var(:result, __MODULE__)
+
+    modified_clauses =
+      Enum.flat_map(clauses, fn
+        {:<-, _meta, [left, right]} = clause ->
+          quote do
+            [
+              code = unquote(Macro.escape(clause)),
+              value = unquote(right),
+              unquote(:<-)({{code, value}, unquote(left)}, {{code, value}, value})
+            ]
+          end
+
+        expr ->
+          [expr]
+      end)
+
+    modified_opts =
+      case opts do
+        [do: do_code] ->
+          else_code =
+            quote do
+              [
+                unquote(:->)(
+                  [{unquote(unmatched_ast_var), unquote(result_var)}],
+                  {:__else__, unquote(unmatched_ast_var), unquote(result_var)}
+                )
+              ]
+            end
+
+          [do: {:__matched__, do_code}, else: else_code]
+
+        [do: do_code, else: else_code] ->
+          else_code =
+            Enum.map(else_code, fn
+              {:->, _meta, [[left], right]} ->
+                quote do
+                  unquote(:->)(
+                    [{unquote(unmatched_ast_var), unquote(left)}],
+                    {:__else__, unquote(unmatched_ast_var), unquote(right)}
+                  )
+                end
+            end)
+
+          final_else_catch_all =
+            quote do
+              unquote(:->)(
+                [{unquote(unmatched_ast_var), unquote(unmatched_else_var)}],
+                {:__else__, unquote(unmatched_ast_var),
+                 raise(WithClauseError, term: unquote(unmatched_else_var))}
+              )
+            end
+
+          [do: {:__matched__, do_code}, else: else_code ++ [final_else_catch_all]]
+      end
+
+    modified = modified_clauses ++ [modified_opts]
+    modified_with_ast = {:with, meta, modified}
+
+    quote do
+      value = unquote(modified_with_ast)
+      {:with, unquote(Macro.escape(ast)), [], value}
+    end
+  end
+
   # Any other AST.
   defp dbg_ast_to_debuggable(ast, _env) do
     quote do: {:value, unquote(escape(ast)), unquote(ast)}
@@ -2828,6 +2897,34 @@ defmodule Macro do
     {formatted, result}
   end
 
+  defp dbg_format_ast_to_debug({:with, ast, [], {:__matched__, value}}, options) do
+    formatted = [
+      dbg_maybe_underline("With clause", options),
+      " (all clauses matched, do block evaluated):\n",
+      dbg_maybe_underline("With expression", options),
+      ":\n",
+      dbg_format_ast_with_value(ast, value, options)
+    ]
+
+    {formatted, value}
+  end
+
+  defp dbg_format_ast_to_debug(
+         {:with, ast, [], {:__else__, {clause_ast, clause_value}, value}},
+         options
+       ) do
+    formatted = [
+      dbg_maybe_underline("With clause unmatched on", options),
+      ":\n",
+      dbg_format_ast_with_value(clause_ast, clause_value, options),
+      dbg_maybe_underline("With expression", options),
+      ":\n",
+      dbg_format_ast_with_value(ast, value, options)
+    ]
+
+    {formatted, value}
+  end
+
   defp dbg_format_ast_to_debug({:value, code_ast, value}, options) do
     {dbg_format_ast_with_value(code_ast, value, options), value}
   end
diff --git a/lib/elixir/test/elixir/macro_test.exs b/lib/elixir/test/elixir/macro_test.exs
index a131caf029c..125580ebe9d 100644
--- a/lib/elixir/test/elixir/macro_test.exs
+++ b/lib/elixir/test/elixir/macro_test.exs
@@ -652,6 +652,107 @@ defmodule MacroTest do
              """
     end
 
+    test "with with/1 (all clauses match)" do
+      opts = %{width: 10, height: 15}
+
+      {result, formatted} =
+        dbg_format(
+          with {:ok, width} <- Map.fetch(opts, :width),
+               double_width = width * 2,
+               IO.puts("just a side effect"),
+               {:ok, height} <- Map.fetch(opts, :height) do
+            {:ok, double_width * height}
+          end
+        )
+
+      assert result == {:ok, 300}
+
+      assert formatted =~ "macro_test.exs"
+
+      assert formatted =~ """
+             With clause (all clauses matched, do block evaluated):
+             With expression:
+             with {:ok, width} <- Map.fetch(opts, :width),
+                  double_width = width * 2,
+                  IO.puts(\"just a side effect\"),
+                  {:ok, height} <- Map.fetch(opts, :height) do
+               {:ok, double_width * height}
+             end #=> {:ok, 300}
+             """
+    end
+
+    test "with with/1 (no else)" do
+      opts = %{width: 10}
+
+      {result, formatted} =
+        dbg_format(
+          with {:ok, width} <- Map.fetch(opts, :width),
+               {:ok, height} <- Map.fetch(opts, :height) do
+            {:ok, width * height}
+          end
+        )
+
+      assert result == :error
+
+      assert formatted =~ "macro_test.exs"
+
+      assert formatted =~ """
+             With clause unmatched on:
+             {:ok, height} <- Map.fetch(opts, :height) #=> :error
+             With expression:
+             with {:ok, width} <- Map.fetch(opts, :width),
+                  {:ok, height} <- Map.fetch(opts, :height) do
+               {:ok, width * height}
+             end #=> :error
+             """
+    end
+
+    test "with with/1 (else clause)" do
+      opts = %{width: 10}
+
+      {result, formatted} =
+        dbg_format(
+          with {:ok, width} <- Map.fetch(opts, :width),
+               {:ok, height} <- Map.fetch(opts, :height) do
+            width * height
+          else
+            :error -> 0
+          end
+        )
+
+      assert result == 0
+
+      assert formatted =~ "macro_test.exs"
+
+      assert formatted =~ """
+             With clause unmatched on:
+             {:ok, height} <- Map.fetch(opts, :height) #=> :error
+             With expression:
+             with {:ok, width} <- Map.fetch(opts, :width),
+                  {:ok, height} <- Map.fetch(opts, :height) do
+               width * height
+             else
+               :error -> 0
+             end #=> 0
+             """
+    end
+
+    test "with with/1 (else clause unmatched)" do
+      assert_raise(
+        WithClauseError,
+        "no with clause matching: :not_found",
+        fn ->
+          dbg(
+            with :ok <- :not_found do
+              :ok
+            else
+              :error -> :error
+            end
+          )
+        end
+      )
+    end
+
     test "with \"syntax_colors: []\" it doesn't print any color sequences" do
       {_result, formatted} = dbg_format("hello")
       refute formatted =~ "\e["