diff --git a/lib/tesla/middleware/compression.ex b/lib/tesla/middleware/compression.ex
index 93fe3a2c..ee5c819c 100644
--- a/lib/tesla/middleware/compression.ex
+++ b/lib/tesla/middleware/compression.ex
@@ -67,9 +67,14 @@ defmodule Tesla.Middleware.Compression do
   def decompress({:ok, env}), do: {:ok, decompress(env)}
   def decompress({:error, reason}), do: {:error, reason}
 
+  # HEAD requests may be used to obtain information on the transfer size and properties
+  # and their empty bodies are not actually valid for the possibly indicated encodings
+  # thus we want to preserve them unchanged.
+  def decompress(%Tesla.Env{method: :head} = env), do: env
+
   def decompress(env) do
     codecs = compression_algorithms(Tesla.get_header(env, "content-encoding"))
-    {decompressed_body, unknown_codecs} = decompress_body(codecs, env.body, [])
+    {decompressed_body, unknown_codecs} = decompress_body(codecs, env.body)
 
     env
     |> put_decompressed_body(decompressed_body)
@@ -84,28 +89,24 @@ defmodule Tesla.Middleware.Compression do
     Tesla.put_header(env, "content-encoding", Enum.join(unknown_codecs, ", "))
   end
 
-  defp decompress_body(_codecs, "" = body, acc) do
-    {body, acc}
-  end
-
-  defp decompress_body([gzip | rest], body, acc) when gzip in ["gzip", "x-gzip"] do
-    decompress_body(rest, :zlib.gunzip(body), acc)
+  defp decompress_body([gzip | rest], body) when gzip in ["gzip", "x-gzip"] do
+    decompress_body(rest, :zlib.gunzip(body))
   end
 
-  defp decompress_body(["deflate" | rest], body, acc) do
-    decompress_body(rest, :zlib.unzip(body), acc)
+  defp decompress_body(["deflate" | rest], body) do
+    decompress_body(rest, :zlib.unzip(body))
   end
 
-  defp decompress_body(["identity" | rest], body, acc) do
-    decompress_body(rest, body, acc)
+  defp decompress_body(["identity" | rest], body) do
+    decompress_body(rest, body)
   end
 
-  defp decompress_body([codec | rest], body, acc) do
-    decompress_body(rest, body, [codec | acc])
+  defp decompress_body([codec | rest], body) do
+    {body, Enum.reverse([codec | rest])}
   end
 
-  defp decompress_body([], body, acc) do
-    {body, acc}
+  defp decompress_body([], body) do
+    {body, []}
   end
 
   defp compression_algorithms(nil) do
@@ -123,7 +124,27 @@ defmodule Tesla.Middleware.Compression do
   defp put_decompressed_body(env, body) do
     env
     |> Tesla.put_body(body)
-    |> Tesla.delete_header("content-length")
+    |> update_content_length(body)
+  end
+
+  # The value of the content-length header wil be inaccurate after decompression.
+  # But setting it is mandatory or strongly encouraged in HTTP/1.0 and HTTP/1.1.
+  # Except, when transfer-encoding is used defining content-length is invalid.
+  # Thus we can neither just drop it nor indiscriminately add it, but will update it if it already exist.
+  # Furthermore, content-length is technically allowed to be specified mutliple times if all values match,
+  # to ensure consistency we must therefore make sure to drop any duplicate definitions while updating.
+  defp update_content_length(env, body) when is_binary(body) do
+    if Tesla.get_header(env, "content-length") != nil do
+      env
+      |> Tesla.delete_header("content-length")
+      |> Tesla.put_header("content-length", "#{byte_size(body)}")
+    else
+      env
+    end
+  end
+
+  defp update_content_length(env, _) do
+    env
   end
 end
 
diff --git a/test/tesla/middleware/compression_test.exs b/test/tesla/middleware/compression_test.exs
index 44d2a739..9b0f5be7 100644
--- a/test/tesla/middleware/compression_test.exs
+++ b/test/tesla/middleware/compression_test.exs
@@ -59,11 +59,33 @@ defmodule Tesla.Middleware.CompressionTest do
             {200, [{"content-type", "text/plain"}, {"content-encoding", "deflate"}],
              :zlib.zip("decompressed deflate")}
 
+          "/multiple-encodings" ->
+            {200, [{"content-type", "text/plain"}, {"content-encoding", "gzip, zstd, gzip"}],
+             :zlib.gzip("decompressed gzip")}
+
           "/response-identity" ->
             {200, [{"content-type", "text/plain"}, {"content-encoding", "identity"}], "unchanged"}
 
           "/response-empty" ->
             {200, [{"content-type", "text/plain"}, {"content-encoding", "gzip"}], ""}
+
+          "/response-with-content-length" ->
+            body = :zlib.gzip("decompressed gzip")
+
+            {200,
+             [
+               {"content-type", "text/plain"},
+               {"content-encoding", "gzip"},
+               {"content-length", "#{byte_size(body)}"}
+             ], body}
+
+          "/response-empty-with-content-length" ->
+            {200,
+             [
+               {"content-type", "text/plain"},
+               {"content-encoding", "gzip"},
+               {"content-length", "4194304"}
+             ], ""}
         end
 
       {:ok, %{env | status: status, headers: headers, body: body}}
@@ -81,16 +103,44 @@ defmodule Tesla.Middleware.CompressionTest do
     assert env.body == "decompressed deflate"
   end
 
+  test "stops decompressing on first unsupported content-encoding" do
+    assert {:ok, env} = CompressionResponseClient.get("/multiple-encodings")
+    assert env.body == "decompressed gzip"
+    assert env.headers == [{"content-type", "text/plain"}, {"content-encoding", "gzip, zstd"}]
+  end
+
   test "return unchanged response for unsupported content-encoding" do
     assert {:ok, env} = CompressionResponseClient.get("/response-identity")
     assert env.body == "unchanged"
     assert env.headers == [{"content-type", "text/plain"}]
   end
 
-  test "return unchanged response for empty body (gzip)" do
-    assert {:ok, env} = CompressionResponseClient.get("/response-empty")
+  test "raises on invalid empty-body response (gzip)" do
+    assert_raise(ErlangError, "Erlang error: :data_error", fn ->
+      CompressionResponseClient.get("/response-empty")
+    end)
+  end
+
+  test "updates existing content-length header" do
+    expected_body = "decompressed gzip"
+    assert {:ok, env} = CompressionResponseClient.get("/response-with-content-length")
+    assert env.body == expected_body
+
+    assert env.headers == [
+             {"content-type", "text/plain"},
+             {"content-length", "#{byte_size(expected_body)}"}
+           ]
+  end
+
+  test "preserves compression headers for HEAD requests" do
+    assert {:ok, env} = CompressionResponseClient.head("/response-empty-with-content-length")
     assert env.body == ""
-    assert env.headers == [{"content-type", "text/plain"}]
+
+    assert env.headers == [
+             {"content-type", "text/plain"},
+             {"content-encoding", "gzip"},
+             {"content-length", "4194304"}
+           ]
   end
 
   defmodule CompressRequestDecompressResponseClient do