diff --git a/src/shrpx_downstream.cc b/src/shrpx_downstream.cc
index b2dec66c..f02a0dc5 100644
--- a/src/shrpx_downstream.cc
+++ b/src/shrpx_downstream.cc
@@ -64,6 +64,7 @@ Downstream::Downstream(Upstream *upstream, int stream_id, int priority)
     request_connection_close_(false),
     request_expect_100_continue_(false),
     request_header_key_prev_(false),
+    request_http2_expect_body_(false),
     chunked_response_(false),
     response_connection_close_(false),
     response_header_key_prev_(false),
@@ -393,6 +394,11 @@ bool Downstream::get_chunked_request() const
   return chunked_request_;
 }
 
+void Downstream::set_chunked_request(bool f)
+{
+  chunked_request_ = f;
+}
+
 bool Downstream::get_request_connection_close() const
 {
   return request_connection_close_;
@@ -403,6 +409,16 @@ void Downstream::set_request_connection_close(bool f)
   request_connection_close_ = f;
 }
 
+bool Downstream::get_request_http2_expect_body() const
+{
+  return request_http2_expect_body_;
+}
+
+void Downstream::set_request_http2_expect_body(bool f)
+{
+  request_http2_expect_body_ = f;
+}
+
 bool Downstream::get_expect_100_continue() const
 {
   return request_expect_100_continue_;
diff --git a/src/shrpx_downstream.h b/src/shrpx_downstream.h
index e68706ef..01e04552 100644
--- a/src/shrpx_downstream.h
+++ b/src/shrpx_downstream.h
@@ -137,8 +137,11 @@ public:
   int get_request_minor() const;
   int push_request_headers();
   bool get_chunked_request() const;
+  void set_chunked_request(bool f);
   bool get_request_connection_close() const;
   void set_request_connection_close(bool f);
+  bool get_request_http2_expect_body() const;
+  void set_request_http2_expect_body(bool f);
   bool get_expect_100_continue() const;
   int push_upload_data_chunk(const uint8_t *data, size_t datalen);
   int end_upload_data();
@@ -274,6 +277,7 @@ private:
   bool request_connection_close_;
   bool request_expect_100_continue_;
   bool request_header_key_prev_;
+  bool request_http2_expect_body_;
 
   bool chunked_response_;
   bool response_connection_close_;
diff --git a/src/shrpx_http2_downstream_connection.cc b/src/shrpx_http2_downstream_connection.cc
index 3e7f2cd8..cf9316e3 100644
--- a/src/shrpx_http2_downstream_connection.cc
+++ b/src/shrpx_http2_downstream_connection.cc
@@ -347,11 +347,6 @@ int Http2DownstreamConnection::push_request_headers()
 
   http2::copy_norm_headers_to_nva(nva, downstream_->get_request_headers());
 
-  bool content_length = false;
-  if(downstream_->get_norm_request_header("content-length") != end_headers) {
-    content_length = true;
-  }
-
   bool chunked_encoding = false;
   auto transfer_encoding =
     downstream_->get_norm_request_header("transfer-encoding");
@@ -414,7 +409,7 @@ int Http2DownstreamConnection::push_request_headers()
   }
 
   if(downstream_->get_request_method() == "CONNECT" ||
-     chunked_encoding || content_length) {
+     chunked_encoding || downstream_->get_request_http2_expect_body()) {
     // Request-body is expected.
     nghttp2_data_provider data_prd;
     data_prd.source.ptr = this;
diff --git a/src/shrpx_http2_upstream.cc b/src/shrpx_http2_upstream.cc
index e2c01a49..cd46c308 100644
--- a/src/shrpx_http2_upstream.cc
+++ b/src/shrpx_http2_upstream.cc
@@ -340,26 +340,17 @@ int on_request_headers(Http2Upstream *upstream,
       return 0;
     }
   }
-  if(!is_connect &&
-     (frame->hd.flags & NGHTTP2_FLAG_END_STREAM) == 0) {
-    auto content_length = http2::get_header(nva, "content-length");
-    if(!content_length || http2::value_lws(content_length)) {
-
-      // TODO We still need content-length here?
-
-      if(upstream->error_reply(downstream, 400) != 0) {
-        upstream->rst_stream(downstream, NGHTTP2_PROTOCOL_ERROR);
-      }
-
-      return 0;
-    }
-  }
 
   downstream->set_request_method(http2::value_to_str(method));
   downstream->set_request_http2_scheme(http2::value_to_str(scheme));
   downstream->set_request_http2_authority(http2::value_to_str(authority));
   downstream->set_request_path(http2::value_to_str(path));
 
+
+  if(!(frame->hd.flags & NGHTTP2_FLAG_END_STREAM)) {
+    downstream->set_request_http2_expect_body(true);
+  }
+
   downstream->inspect_http2_request();
 
   auto dconn = upstream->get_client_handler()->get_downstream_connection();
diff --git a/src/shrpx_http_downstream_connection.cc b/src/shrpx_http_downstream_connection.cc
index 576e4f3d..9494f5a2 100644
--- a/src/shrpx_http_downstream_connection.cc
+++ b/src/shrpx_http_downstream_connection.cc
@@ -164,6 +164,13 @@ int HttpDownstreamConnection::push_request_headers()
     hdrs += "\r\n";
   }
 
+  if(downstream_->get_request_http2_expect_body() &&
+     downstream_->get_norm_request_header("content-length") == end_headers) {
+
+    downstream_->set_chunked_request(true);
+    hdrs += "Transfer-Encoding: chunked\r\n";
+  }
+
   if(downstream_->get_request_connection_close()) {
     hdrs += "Connection: close\r\n";
   }
diff --git a/src/shrpx_spdy_upstream.cc b/src/shrpx_spdy_upstream.cc
index 00760069..f5485231 100644
--- a/src/shrpx_spdy_upstream.cc
+++ b/src/shrpx_spdy_upstream.cc
@@ -204,6 +204,10 @@ void on_ctrl_recv_callback
       downstream->set_request_path(path);
     }
 
+    if(!(frame->syn_stream.hd.flags & SPDYLAY_CTRL_FLAG_FIN)) {
+      downstream->set_request_http2_expect_body(true);
+    }
+
     downstream->inspect_http2_request();
 
     if(LOG_ENABLED(INFO)) {