diff --git a/lib/bamboo/adapters/render/raw.ex b/lib/bamboo/adapters/render/raw.ex
index 1f3d840..e42a1e1 100644
--- a/lib/bamboo/adapters/render/raw.ex
+++ b/lib/bamboo/adapters/render/raw.ex
@@ -165,13 +165,19 @@ defmodule BambooSes.Render.Raw do
       [
         {"From", mailbox(email.from)},
         {"Subject", email.subject}
-      ] ++ Map.to_list(email.headers)
+      ] ++ Enum.map(email.headers, &preprocess_header/1)
 
     Enum.filter(headers, fn i -> elem(i, 1) != "" end)
   end
 
   defp mailbox({name, address}), do: "#{name} <#{address}>"
 
+  defp preprocess_header({"Reply-To" = key, {_name, _address} = value}) do
+    {key, BambooSes.Encoding.prepare_address(value)}
+  end
+
+  defp preprocess_header({key, value}), do: {key, value}
+
   defp compile_parts(email) do
     [
       {:plain, email.text_body},
diff --git a/test/lib/bamboo/adapters/ses_adapter_test.exs b/test/lib/bamboo/adapters/ses_adapter_test.exs
index dbae6d1..3cbb7b7 100644
--- a/test/lib/bamboo/adapters/ses_adapter_test.exs
+++ b/test/lib/bamboo/adapters/ses_adapter_test.exs
@@ -340,6 +340,34 @@ defmodule Bamboo.SesAdapterTest do
     SesAdapter.deliver(TestHelpers.new_email(), %{})
   end
 
+  test "does not crash with Reply-To tuple and sending raw content" do
+    expected_request_fn = fn _, _, body, _, _ ->
+      {:ok, message} = Jason.decode(body)
+
+      %{
+        "Content" => %{
+          "Raw" => %{
+            "Data" => raw_content
+          }
+        }
+      } = message
+
+      email = EmailParser.parse(raw_content)
+
+      assert header_value = EmailParser.header(email, "Reply-To")
+      assert header_value == "John Schmidt <reply-to@example.com>"
+
+      {:ok, %{status_code: 200, body: body}}
+    end
+
+    expect(HttpMock, :request, expected_request_fn)
+
+    TestHelpers.new_email()
+    |> Email.put_header("X-Custom-Header", "header-value")
+    |> Email.put_header("Reply-To", {"John Schmidt", "reply-to@example.com"})
+    |> SesAdapter.deliver(%{})
+  end
+
   test "uses configured aws region" do
     expect(HttpMock, :request, fn _,
                                   "https://email.eu-west-1.amazonaws.com/v2/email/outbound-emails",