diff --git a/.gitignore b/.gitignore
index 8c6f556..92f05d3 100644
--- a/.gitignore
+++ b/.gitignore
@@ -25,6 +25,7 @@ thousand_island-*.tar
 # Ignore dialyzer caches
 /priv/plts/
 
+/tmp/
 
 # ElixirLS
-/.elixir_ls
\ No newline at end of file
+/.elixir_ls
diff --git a/lib/thousand_island/transports/ssl.ex b/lib/thousand_island/transports/ssl.ex
index db15bb4..35c81d4 100644
--- a/lib/thousand_island/transports/ssl.ex
+++ b/lib/thousand_island/transports/ssl.ex
@@ -45,6 +45,9 @@ defmodule ThousandIsland.Transports.SSL do
 
   @hardcoded_options [mode: :binary, active: false]
 
+  # Default chunk size: 8MB - balances memory usage vs syscall overhead
+  @sendfile_chunk_size 8 * 1024 * 1024
+
   @impl ThousandIsland.Transport
   @spec listen(:inet.port_number(), [:ssl.tls_server_option()]) ::
           ThousandIsland.Transport.on_listen()
@@ -126,18 +129,12 @@ defmodule ThousandIsland.Transports.SSL do
           length :: non_neg_integer()
         ) :: ThousandIsland.Transport.on_sendfile()
   def sendfile(socket, filename, offset, length) do
-    # We can't use :file.sendfile here since it works on clear sockets, not ssl
-    # sockets. Build our own (much slower and not optimized for large files) version.
-    case :file.open(filename, [:raw]) do
+    # We can't use :file.sendfile here since it works on clear sockets, not ssl sockets.
+    # Build our own version with chunking for large files.
+    case :file.open(filename, [:read, :raw, :binary]) do
       {:ok, fd} ->
         try do
-          with {:ok, data} <- :file.pread(fd, offset, length),
-               :ok <- :ssl.send(socket, data) do
-            {:ok, length}
-          else
-            :eof -> {:error, :eof}
-            {:error, reason} -> {:error, reason}
-          end
+          sendfile_loop(socket, fd, offset, length, 0)
         after
           :file.close(fd)
         end
@@ -147,6 +144,28 @@ defmodule ThousandIsland.Transports.SSL do
     end
   end
 
+  defp sendfile_loop(_socket, _fd, _offset, sent, sent) when 0 != sent do
+    {:ok, sent}
+  end
+
+  defp sendfile_loop(socket, fd, offset, length, sent) do
+    with read_size <- chunk_size(length, sent, @sendfile_chunk_size),
+         {:ok, data} <- :file.pread(fd, offset, read_size),
+         :ok <- :ssl.send(socket, data) do
+      now_sent = byte_size(data)
+      sendfile_loop(socket, fd, offset + now_sent, length, sent + now_sent)
+    else
+      :eof ->
+        {:ok, sent}
+
+      {:error, reason} ->
+        {:error, reason}
+    end
+  end
+
+  defp chunk_size(0, _sent, chunk_size), do: chunk_size
+  defp chunk_size(length, sent, chunk), do: min(length - sent, chunk)
+
   @impl ThousandIsland.Transport
   @spec getopts(socket(), ThousandIsland.Transport.socket_get_options()) ::
           ThousandIsland.Transport.on_getopts()
diff --git a/lib/thousand_island/transports/tcp.ex b/lib/thousand_island/transports/tcp.ex
index a7d7941..f0e9e2d 100644
--- a/lib/thousand_island/transports/tcp.ex
+++ b/lib/thousand_island/transports/tcp.ex
@@ -107,7 +107,7 @@ defmodule ThousandIsland.Transports.TCP do
           length :: non_neg_integer()
         ) :: ThousandIsland.Transport.on_sendfile()
   def sendfile(socket, filename, offset, length) do
-    case :file.open(filename, [:raw]) do
+    case :file.open(filename, [:read, :raw, :binary]) do
       {:ok, fd} ->
         try do
           :file.sendfile(fd, socket, offset, length, [])
diff --git a/test/thousand_island/socket_test.exs b/test/thousand_island/socket_test.exs
index 4cb2313..5427162 100644
--- a/test/thousand_island/socket_test.exs
+++ b/test/thousand_island/socket_test.exs
@@ -3,15 +3,22 @@ defmodule ThousandIsland.SocketTest do
 
   use Machete
 
-  def gen_tcp_setup(_context) do
-    {:ok, %{client_mod: :gen_tcp, client_opts: [active: false], server_opts: []}}
+  @eight_mb_chunks 8 * 1024 * 1024
+  @large_file_size 256 * 1024 * 1024
+
+  def gen_tcp_setup(context) do
+    if context[:tmp_dir], do: maybe_create_big_file(context.tmp_dir)
+    {:ok, %{client_mod: :gen_tcp, client_opts: [:binary, active: false], server_opts: []}}
   end
 
-  def ssl_setup(_context) do
+  def ssl_setup(context) do
+    if context[:tmp_dir], do: maybe_create_big_file(context.tmp_dir)
+
     {:ok,
      %{
        client_mod: :ssl,
        client_opts: [
+         :binary,
          active: false,
          verify: :verify_peer,
          cacertfile: Path.join(__DIR__, "../support/ca.pem")
@@ -50,6 +57,18 @@ defmodule ThousandIsland.SocketTest do
     end
   end
 
+  defmodule LargeSendfile do
+    use ThousandIsland.Handler
+
+    @impl ThousandIsland.Handler
+    def handle_connection(socket, state) do
+      large_file_path = Path.join(state[:tmp_dir], "large_sendfile")
+      ThousandIsland.Socket.sendfile(socket, large_file_path, 0, 0)
+      send(state[:test_pid], Process.info(self(), :monitored_by))
+      {:close, state}
+    end
+  end
+
   defmodule Closer do
     use ThousandIsland.Handler
 
@@ -88,7 +107,7 @@ defmodule ThousandIsland.SocketTest do
         {:ok, client} = context.client_mod.connect(~c"localhost", port, context.client_opts)
 
         assert context.client_mod.send(client, "HELLO") == :ok
-        assert context.client_mod.recv(client, 0) == {:ok, ~c"HELLO"}
+        assert context.client_mod.recv(client, 0) == {:ok, "HELLO"}
       end
 
       test "it should close connections", context do
@@ -105,7 +124,7 @@ defmodule ThousandIsland.SocketTest do
         {:ok, client} = context.client_mod.connect(~c"localhost", port, context.client_opts)
 
         :ok = context.client_mod.send(client, "HELLO")
-        {:ok, ~c"HELLO"} = context.client_mod.recv(client, 0)
+        {:ok, "HELLO"} = context.client_mod.recv(client, 0)
         context.client_mod.close(client)
 
         assert_receive {:telemetry, [:thousand_island, :connection, :recv], measurements,
@@ -151,7 +170,18 @@ defmodule ThousandIsland.SocketTest do
       server_opts = Keyword.put(context.server_opts, :handler_options, test_pid: self())
       {:ok, port} = start_handler(Sendfile, server_opts)
       {:ok, client} = context.client_mod.connect(~c"localhost", port, context.client_opts)
-      assert context.client_mod.recv(client, 9) == {:ok, ~c"ABCDEFBCD"}
+      assert context.client_mod.recv(client, 9) == {:ok, "ABCDEFBCD"}
+      assert_receive {:monitored_by, []}
+    end
+
+    @tag :tmp_dir
+    test "it should send large files", %{tmp_dir: tmp_dir} = context do
+      opts = [test_pid: self(), tmp_dir: tmp_dir]
+      server_opts = Keyword.put(context.server_opts, :handler_options, opts)
+      {:ok, port} = start_handler(LargeSendfile, server_opts)
+      {:ok, client} = context.client_mod.connect(~c"localhost", port, context.client_opts)
+      total_received = receive_all_data(context.client_mod, client, @large_file_size, "")
+      assert byte_size(total_received) == @large_file_size
       assert_receive {:monitored_by, []}
     end
   end
@@ -193,7 +223,18 @@ defmodule ThousandIsland.SocketTest do
       server_opts = Keyword.put(context.server_opts, :handler_options, test_pid: self())
       {:ok, port} = start_handler(Sendfile, server_opts)
       {:ok, client} = context.client_mod.connect(~c"localhost", port, context.client_opts)
-      assert context.client_mod.recv(client, 9) == {:ok, ~c"ABCDEFBCD"}
+      assert context.client_mod.recv(client, 9) == {:ok, "ABCDEFBCD"}
+      assert_receive {:monitored_by, [_pid]}
+    end
+
+    @tag :tmp_dir
+    test "it should send large files", %{tmp_dir: tmp_dir} = context do
+      opts = [test_pid: self(), tmp_dir: tmp_dir]
+      server_opts = Keyword.put(context.server_opts, :handler_options, opts)
+      {:ok, port} = start_handler(LargeSendfile, server_opts)
+      {:ok, client} = context.client_mod.connect(~c"localhost", port, context.client_opts)
+      total_received = receive_all_data(context.client_mod, client, @large_file_size, "")
+      assert byte_size(total_received) == @large_file_size
       assert_receive {:monitored_by, [_pid]}
     end
   end
@@ -204,4 +245,32 @@ defmodule ThousandIsland.SocketTest do
     {:ok, {_ip, port}} = ThousandIsland.listener_info(server_pid)
     {:ok, port}
   end
+
+  defp maybe_create_big_file(tmp_dir) do
+    path = Path.join(tmp_dir, "large_sendfile")
+
+    unless File.exists?(path) and File.stat!(path).size == @large_file_size do
+      # Create a large file by writing 8MB chunks to avoid memory issues
+      chunks_needed = div(@large_file_size, @eight_mb_chunks)
+      chunk_data = :binary.copy(<<0>>, @eight_mb_chunks)
+      {:ok, file} = File.open(path, [:write, :binary])
+      for _i <- 1..chunks_needed, do: IO.binwrite(file, chunk_data)
+      File.close(file)
+    end
+  end
+
+  defp receive_all_data(_, _, total_size, acc) when total_size <= 0, do: acc
+
+  defp receive_all_data(client_mod, client, total_size, acc) do
+    case client_mod.recv(client, @eight_mb_chunks) do
+      {:ok, data} ->
+        receive_all_data(client_mod, client, total_size - byte_size(data), acc <> data)
+
+      {:error, :closed} when byte_size(acc) == total_size ->
+        acc
+
+      {:error, reason} ->
+        raise "Failed to receive data: #{inspect(reason)}"
+    end
+  end
 end