diff --git a/lib/elixir/lib/macro.ex b/lib/elixir/lib/macro.ex
index c3803470ff1..053a8fd9369 100644
--- a/lib/elixir/lib/macro.ex
+++ b/lib/elixir/lib/macro.ex
@@ -2674,6 +2674,84 @@ defmodule Macro do
     end
   end
 
+  defp dbg_ast_to_debuggable({:with, meta, args} = ast, _env) do
+    {opts, clauses} = List.pop_at(args, -1)
+
+    acc_var = unique_var(:acc, __MODULE__)
+
+    modified_clauses =
+      Enum.flat_map(clauses, fn
+        # We only detail assignments and pattern-matching clauses that
+        # can be helpful to understand how the result is constructed.
+        {:<-, _meta, [left, right]} ->
+          modified_left =
+            case left do
+              {:when, meta, [pattern, guard]} -> {:when, meta, [{pattern, quote(do: _)}, guard]}
+              pattern -> {pattern, quote(do: _)}
+            end
+
+          quote do
+            [
+              value = unquote(right),
+              unquote(acc_var) = [{unquote(escape(right)), value} | unquote(acc_var)],
+              unquote(modified_left) <- {value, unquote(acc_var)}
+            ]
+          end
+
+        {:=, _meta, [left, right]} ->
+          quote do
+            [
+              value = unquote(right),
+              unquote(acc_var) = [{unquote(escape(right)), value} | unquote(acc_var)],
+              unquote(left) = value
+            ]
+          end
+
+        # Other expressions like side effects are omitted.
+        expr ->
+          [expr]
+      end)
+
+    modified_opts =
+      Enum.map(opts, fn
+        {:do, do_block} ->
+          {:do, {do_block, acc_var}}
+
+        {:else, else_block} ->
+          clauses =
+            Enum.map(else_block, fn
+              {:->, meta, [[{:when, meta2, [pattern, guard]}], right]} ->
+                {:->, meta, [[{:when, meta2, [{pattern, acc_var}, guard]}], {right, acc_var}]}
+
+              {:->, meta, [[left], right]} ->
+                {:->, meta, [[{left, acc_var}], {right, acc_var}]}
+
+              invalid ->
+                invalid
+            end)
+
+          error_clause =
+            quote do
+              {other, _acc} -> raise WithClauseError, term: other
+            end
+
+          {:else, clauses ++ error_clause}
+
+        invalid ->
+          invalid
+      end)
+
+    modified_with_ast = {:with, meta, modified_clauses ++ [modified_opts]}
+
+    quote do
+      unquote(acc_var) = []
+
+      {value, acc} = unquote(modified_with_ast)
+
+      {:with, unquote(escape(ast)), Enum.reverse(acc), value}
+    end
+  end
+
   # Any other AST.
   defp dbg_ast_to_debuggable(ast, _env) do
     quote do: {:value, unquote(escape(ast)), unquote(ast)}
@@ -2828,6 +2906,25 @@ defmodule Macro do
     {formatted, result}
   end
 
+  defp dbg_format_ast_to_debug({:with, ast, clauses, result}, options) do
+    formatted_clauses =
+      Enum.map(clauses, fn {clause_ast, clause_result} ->
+        dbg_format_ast_with_value(clause_ast, clause_result, options)
+      end)
+
+    formatted = [
+      dbg_maybe_underline("With clauses", options),
+      ":\n",
+      formatted_clauses,
+      ?\n,
+      dbg_maybe_underline("With expression", options),
+      ":\n",
+      dbg_format_ast_with_value(ast, result, options)
+    ]
+
+    {formatted, result}
+  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..142968a4780 100644
--- a/lib/elixir/test/elixir/macro_test.exs
+++ b/lib/elixir/test/elixir/macro_test.exs
@@ -652,6 +652,162 @@ 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 clauses:
+             Map.fetch(opts, :width) #=> {:ok, 10}
+             width * 2 #=> 20
+             Map.fetch(opts, :height) #=> {:ok, 15}
+
+             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 clauses:
+             Map.fetch(opts, :width) #=> {:ok, 10}
+             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 clauses:
+             Map.fetch(opts, :width) #=> {:ok, 10}
+             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 (guard)" do
+      opts = %{width: 10, height: 0.0}
+
+      {result, formatted} =
+        dbg_format(
+          with {:ok, width} when is_integer(width) <- Map.fetch(opts, :width),
+               {:ok, height} when is_integer(height) <- Map.fetch(opts, :height) do
+            width * height
+          else
+            _ -> nil
+          end
+        )
+
+      assert result == nil
+      assert formatted =~ "macro_test.exs"
+
+      assert formatted =~ """
+             With clauses:
+             Map.fetch(opts, :width) #=> {:ok, 10}
+             Map.fetch(opts, :height) #=> {:ok, 0.0}
+
+             With expression:
+             with {:ok, width} when is_integer(width) <- Map.fetch(opts, :width),
+                  {:ok, height} when is_integer(height) <- Map.fetch(opts, :height) do
+               width * height
+             else
+               _ -> nil
+             end #=> nil
+             """
+    end
+
+    test "with with/1 (guard in else)" do
+      opts = %{}
+
+      {result, _formatted} =
+        dbg_format(
+          with {:ok, width} <- Map.fetch(opts, :width) do
+            width
+          else
+            other when is_integer(other) -> :int
+            other when is_atom(other) -> :atom
+          end
+        )
+
+      assert result == :atom
+    end
+
+    test "with with/1 respects the WithClauseError" do
+      value = Enum.random([:unexpected])
+
+      error =
+        assert_raise WithClauseError, fn ->
+          dbg(
+            with :ok <- value do
+              true
+            else
+              :error -> false
+            end
+          )
+        end
+
+      assert error.term == :unexpected
+    end
+
     test "with \"syntax_colors: []\" it doesn't print any color sequences" do
       {_result, formatted} = dbg_format("hello")
       refute formatted =~ "\e["