diff --git a/net/http/http_basic_stream.cc b/net/http/http_basic_stream.cc
index d82e153..1dcf2b0 100644
--- a/net/http/http_basic_stream.cc
+++ b/net/http/http_basic_stream.cc
@@ -176,11 +176,11 @@
   parser()->GetSSLCertRequestInfo(cert_request_info);
 }
 
-bool HttpBasicStream::GetRemoteEndpoint(IPEndPoint* endpoint) {
+int HttpBasicStream::GetRemoteEndpoint(IPEndPoint* endpoint) {
   if (!state_.connection() || !state_.connection()->socket())
-    return false;
+    return ERR_SOCKET_NOT_CONNECTED;
 
-  return state_.connection()->socket()->GetPeerAddress(endpoint) == OK;
+  return state_.connection()->socket()->GetPeerAddress(endpoint);
 }
 
 void HttpBasicStream::Drain(HttpNetworkSession* session) {
diff --git a/net/http/http_basic_stream.h b/net/http/http_basic_stream.h
index 8c765a8..2d1c561 100644
--- a/net/http/http_basic_stream.h
+++ b/net/http/http_basic_stream.h
@@ -87,7 +87,7 @@
 
   void GetSSLCertRequestInfo(SSLCertRequestInfo* cert_request_info) override;
 
-  bool GetRemoteEndpoint(IPEndPoint* endpoint) override;
+  int GetRemoteEndpoint(IPEndPoint* endpoint) override;
 
   void Drain(HttpNetworkSession* session) override;
 
diff --git a/net/http/http_network_transaction.cc b/net/http/http_network_transaction.cc
index 977b28c..a28530c 100644
--- a/net/http/http_network_transaction.cc
+++ b/net/http/http_network_transaction.cc
@@ -908,9 +908,18 @@
   // HttpStream::GetAcceptChViaAlps() needs the HttpRequestInfo to retrieve
   // the ACCEPT_CH frame payload.
   stream_->RegisterRequest(request_);
-  stream_->GetRemoteEndpoint(&remote_endpoint_);
   next_state_ = STATE_CONNECTED_CALLBACK_COMPLETE;
 
+  int result = stream_->GetRemoteEndpoint(&remote_endpoint_);
+  if (result != OK) {
+    // `GetRemoteEndpoint()` fails when the underlying socket is not connected
+    // anymore, even though the peer's address is known. This can happen when
+    // we picked a socket from socket pools while it was still connected, but
+    // the remote side closes it before we get a chance to send our request.
+    // See if we should retry the request based on the error code we got.
+    return HandleIOError(result);
+  }
+
   if (connected_callback_.is_null()) {
     return OK;
   }
@@ -1581,9 +1590,10 @@
 }
 
 // This method determines whether it is safe to resend the request after an
-// IO error.  It can only be called in response to request header or body
-// write errors or response header read errors.  It should not be used in
-// other cases, such as a Connect error.
+// IO error. It should only be called in response to errors received before
+// final set of response headers have been successfully parsed, that the
+// transaction may need to be retried on.
+// It should not be used in other cases, such as a Connect error.
 int HttpNetworkTransaction::HandleIOError(int error) {
   // Because the peer may request renegotiation with client authentication at
   // any time, check and handle client authentication errors.
@@ -1730,9 +1740,7 @@
   // NOTE: we resend a request only if we reused a keep-alive connection.
   // This automatically prevents an infinite resend loop because we'll run
   // out of the cached keep-alive connections eventually.
-  if (connection_is_proven && !has_received_headers)
-    return true;
-  return false;
+  return connection_is_proven && !has_received_headers;
 }
 
 bool HttpNetworkTransaction::HasExceededMaxRetries() const {
diff --git a/net/http/http_response_body_drainer_unittest.cc b/net/http/http_response_body_drainer_unittest.cc
index ed70a0d..a8ffe04 100644
--- a/net/http/http_response_body_drainer_unittest.cc
+++ b/net/http/http_response_body_drainer_unittest.cc
@@ -125,7 +125,9 @@
   }
   void GetSSLInfo(SSLInfo* ssl_info) override {}
   void GetSSLCertRequestInfo(SSLCertRequestInfo* cert_request_info) override {}
-  bool GetRemoteEndpoint(IPEndPoint* endpoint) override { return false; }
+  int GetRemoteEndpoint(IPEndPoint* endpoint) override {
+    return ERR_UNEXPECTED;
+  }
 
   // Mocked API
   int ReadResponseBody(IOBuffer* buf,
diff --git a/net/http/http_stream.h b/net/http/http_stream.h
index 04d1507f..80712a6 100644
--- a/net/http/http_stream.h
+++ b/net/http/http_stream.h
@@ -171,9 +171,9 @@
   virtual void GetSSLCertRequestInfo(SSLCertRequestInfo* cert_request_info) = 0;
 
   // Gets the remote endpoint of the socket that the HTTP stream is using, if
-  // any. Returns true and fills in |endpoint| if it is available; returns false
-  // and does not modify |endpoint| if it is unavailable.
-  virtual bool GetRemoteEndpoint(IPEndPoint* endpoint) = 0;
+  // any. Returns OK and fills in |endpoint| if it is available; returns an
+  // error and does not modify |endpoint| otherwise.
+  virtual int GetRemoteEndpoint(IPEndPoint* endpoint) = 0;
 
   // In the case of an HTTP error or redirect, flush the response body (usually
   // a simple error or "this page has moved") so that we can re-use the
diff --git a/net/http/http_stream_factory_unittest.cc b/net/http/http_stream_factory_unittest.cc
index 7145365..6f5f552 100644
--- a/net/http/http_stream_factory_unittest.cc
+++ b/net/http/http_stream_factory_unittest.cc
@@ -163,7 +163,9 @@
   }
   void GetSSLInfo(SSLInfo* ssl_info) override {}
   void GetSSLCertRequestInfo(SSLCertRequestInfo* cert_request_info) override {}
-  bool GetRemoteEndpoint(IPEndPoint* endpoint) override { return false; }
+  int GetRemoteEndpoint(IPEndPoint* endpoint) override {
+    return ERR_UNEXPECTED;
+  }
   void Drain(HttpNetworkSession* session) override {}
   void PopulateNetErrorDetails(NetErrorDetails* details) override { return; }
   void SetPriority(RequestPriority priority) override {}
diff --git a/net/quic/quic_chromium_client_session.cc b/net/quic/quic_chromium_client_session.cc
index b54e6e5..2f9d8e5 100644
--- a/net/quic/quic_chromium_client_session.cc
+++ b/net/quic/quic_chromium_client_session.cc
@@ -1409,9 +1409,9 @@
   return crypto_stream_.get();
 }
 
-bool QuicChromiumClientSession::GetRemoteEndpoint(IPEndPoint* endpoint) {
+int QuicChromiumClientSession::GetRemoteEndpoint(IPEndPoint* endpoint) {
   *endpoint = ToIPEndPoint(peer_address());
-  return true;
+  return OK;
 }
 
 // TODO(rtenneti): Add unittests for GetSSLInfo which exercise the various ways
diff --git a/net/quic/quic_chromium_client_session.h b/net/quic/quic_chromium_client_session.h
index 806fa2a..58c70a036 100644
--- a/net/quic/quic_chromium_client_session.h
+++ b/net/quic/quic_chromium_client_session.h
@@ -699,7 +699,7 @@
   void OnStreamClosed(quic::QuicStreamId stream_id) override;
 
   // MultiplexedSession methods:
-  bool GetRemoteEndpoint(IPEndPoint* endpoint) override;
+  int GetRemoteEndpoint(IPEndPoint* endpoint) override;
   bool GetSSLInfo(SSLInfo* ssl_info) const override;
   base::StringPiece GetAcceptChViaAlps(
       const url::SchemeHostPort& scheme_host_port) const override;
diff --git a/net/spdy/multiplexed_http_stream.cc b/net/spdy/multiplexed_http_stream.cc
index 236fb40..b4e47bc 100644
--- a/net/spdy/multiplexed_http_stream.cc
+++ b/net/spdy/multiplexed_http_stream.cc
@@ -19,7 +19,7 @@
 
 MultiplexedHttpStream::~MultiplexedHttpStream() = default;
 
-bool MultiplexedHttpStream::GetRemoteEndpoint(IPEndPoint* endpoint) {
+int MultiplexedHttpStream::GetRemoteEndpoint(IPEndPoint* endpoint) {
   return session_->GetRemoteEndpoint(endpoint);
 }
 
diff --git a/net/spdy/multiplexed_http_stream.h b/net/spdy/multiplexed_http_stream.h
index 27d4ce5c..56e1cd0 100644
--- a/net/spdy/multiplexed_http_stream.h
+++ b/net/spdy/multiplexed_http_stream.h
@@ -21,7 +21,7 @@
       std::unique_ptr<MultiplexedSessionHandle> session);
   ~MultiplexedHttpStream() override;
 
-  bool GetRemoteEndpoint(IPEndPoint* endpoint) override;
+  int GetRemoteEndpoint(IPEndPoint* endpoint) override;
   void GetSSLInfo(SSLInfo* ssl_info) override;
   void GetSSLCertRequestInfo(SSLCertRequestInfo* cert_request_info) override;
   void Drain(HttpNetworkSession* session) override;
diff --git a/net/spdy/multiplexed_session.cc b/net/spdy/multiplexed_session.cc
index 06bd12a..f51ccde 100644
--- a/net/spdy/multiplexed_session.cc
+++ b/net/spdy/multiplexed_session.cc
@@ -14,9 +14,9 @@
 
 MultiplexedSessionHandle::~MultiplexedSessionHandle() = default;
 
-bool MultiplexedSessionHandle::GetRemoteEndpoint(IPEndPoint* endpoint) {
+int MultiplexedSessionHandle::GetRemoteEndpoint(IPEndPoint* endpoint) {
   if (!session_)
-    return false;
+    return ERR_SOCKET_NOT_CONNECTED;
 
   return session_->GetRemoteEndpoint(endpoint);
 }
diff --git a/net/spdy/multiplexed_session.h b/net/spdy/multiplexed_session.h
index c5110cc..0aaa2669 100644
--- a/net/spdy/multiplexed_session.h
+++ b/net/spdy/multiplexed_session.h
@@ -26,9 +26,9 @@
   virtual bool GetSSLInfo(SSLInfo* ssl_info) const = 0;
 
   // Gets the remote endpoint of the socket that the HTTP stream is using, if
-  // any. Returns true and fills in |endpoint| if it is available; returns false
-  // and does not modify |endpoint| if it is unavailable.
-  virtual bool GetRemoteEndpoint(IPEndPoint* endpoint) = 0;
+  // any. Returns OK and fills in |endpoint| if it is available; returns an
+  // error and does not modify |endpoint| otherwise.
+  virtual int GetRemoteEndpoint(IPEndPoint* endpoint) = 0;
 
   // The value corresponding to |scheme_host_port| in the ACCEPT_CH frame
   // received during TLS handshake via the ALPS extension, or the empty string
@@ -50,9 +50,9 @@
   virtual ~MultiplexedSessionHandle();
 
   // Gets the remote endpoint of the socket that the HTTP stream is using, if
-  // any. Returns true and fills in |endpoint| if it is available; returns false
-  // and does not modify |endpoint| if it is unavailable.
-  bool GetRemoteEndpoint(IPEndPoint* endpoint);
+  // any. Returns OK and fills in |endpoint| if it is available; returns an
+  // error and does not modify |endpoint| otherwise.
+  int GetRemoteEndpoint(IPEndPoint* endpoint);
 
   // Fills SSL info in |ssl_info| and returns true when SSL is in use.
   bool GetSSLInfo(SSLInfo* ssl_info) const;
diff --git a/net/spdy/spdy_http_stream.cc b/net/spdy/spdy_http_stream.cc
index 09525d2..f4db5b6 100644
--- a/net/spdy/spdy_http_stream.cc
+++ b/net/spdy/spdy_http_stream.cc
@@ -704,11 +704,11 @@
   std::move(response_callback_).Run(rv);
 }
 
-bool SpdyHttpStream::GetRemoteEndpoint(IPEndPoint* endpoint) {
+int SpdyHttpStream::GetRemoteEndpoint(IPEndPoint* endpoint) {
   if (!spdy_session_)
-    return false;
+    return ERR_SOCKET_NOT_CONNECTED;
 
-  return spdy_session_->GetPeerAddress(endpoint) == OK;
+  return spdy_session_->GetPeerAddress(endpoint);
 }
 
 void SpdyHttpStream::PopulateNetErrorDetails(NetErrorDetails* details) {
diff --git a/net/spdy/spdy_http_stream.h b/net/spdy/spdy_http_stream.h
index ddf9e25..7dfc6e8 100644
--- a/net/spdy/spdy_http_stream.h
+++ b/net/spdy/spdy_http_stream.h
@@ -86,7 +86,7 @@
   bool GetAlternativeService(
       AlternativeService* alternative_service) const override;
   bool GetLoadTimingInfo(LoadTimingInfo* load_timing_info) const override;
-  bool GetRemoteEndpoint(IPEndPoint* endpoint) override;
+  int GetRemoteEndpoint(IPEndPoint* endpoint) override;
   void PopulateNetErrorDetails(NetErrorDetails* details) override;
   void SetPriority(RequestPriority priority) override;
   const std::set<std::string>& GetDnsAliases() const override;
diff --git a/net/spdy/spdy_session.cc b/net/spdy/spdy_session.cc
index d0f186b..0733e87 100644
--- a/net/spdy/spdy_session.cc
+++ b/net/spdy/spdy_session.cc
@@ -1507,8 +1507,8 @@
   return LOAD_STATE_IDLE;
 }
 
-bool SpdySession::GetRemoteEndpoint(IPEndPoint* endpoint) {
-  return GetPeerAddress(endpoint) == OK;
+int SpdySession::GetRemoteEndpoint(IPEndPoint* endpoint) {
+  return GetPeerAddress(endpoint);
 }
 
 bool SpdySession::GetSSLInfo(SSLInfo* ssl_info) const {
diff --git a/net/spdy/spdy_session.h b/net/spdy/spdy_session.h
index 5dfc306..4566fbe 100644
--- a/net/spdy/spdy_session.h
+++ b/net/spdy/spdy_session.h
@@ -530,7 +530,7 @@
   LoadState GetLoadState() const;
 
   // MultiplexedSession methods:
-  bool GetRemoteEndpoint(IPEndPoint* endpoint) override;
+  int GetRemoteEndpoint(IPEndPoint* endpoint) override;
   bool GetSSLInfo(SSLInfo* ssl_info) const override;
   base::StringPiece GetAcceptChViaAlps(
       const url::SchemeHostPort& scheme_host_port) const override;
diff --git a/net/websockets/websocket_basic_handshake_stream.cc b/net/websockets/websocket_basic_handshake_stream.cc
index d72fe99..2b20820 100644
--- a/net/websockets/websocket_basic_handshake_stream.cc
+++ b/net/websockets/websocket_basic_handshake_stream.cc
@@ -363,11 +363,11 @@
   parser()->GetSSLCertRequestInfo(cert_request_info);
 }
 
-bool WebSocketBasicHandshakeStream::GetRemoteEndpoint(IPEndPoint* endpoint) {
+int WebSocketBasicHandshakeStream::GetRemoteEndpoint(IPEndPoint* endpoint) {
   if (!state_.connection() || !state_.connection()->socket())
-    return false;
+    return ERR_SOCKET_NOT_CONNECTED;
 
-  return state_.connection()->socket()->GetPeerAddress(endpoint) == OK;
+  return state_.connection()->socket()->GetPeerAddress(endpoint);
 }
 
 void WebSocketBasicHandshakeStream::PopulateNetErrorDetails(
diff --git a/net/websockets/websocket_basic_handshake_stream.h b/net/websockets/websocket_basic_handshake_stream.h
index 78b5444..8496184 100644
--- a/net/websockets/websocket_basic_handshake_stream.h
+++ b/net/websockets/websocket_basic_handshake_stream.h
@@ -76,7 +76,7 @@
   bool GetLoadTimingInfo(LoadTimingInfo* load_timing_info) const override;
   void GetSSLInfo(SSLInfo* ssl_info) override;
   void GetSSLCertRequestInfo(SSLCertRequestInfo* cert_request_info) override;
-  bool GetRemoteEndpoint(IPEndPoint* endpoint) override;
+  int GetRemoteEndpoint(IPEndPoint* endpoint) override;
   void Drain(HttpNetworkSession* session) override;
   void SetPriority(RequestPriority priority) override;
   void PopulateNetErrorDetails(NetErrorDetails* details) override;
diff --git a/net/websockets/websocket_http2_handshake_stream.cc b/net/websockets/websocket_http2_handshake_stream.cc
index 65d2fc6..c0d9c83 100644
--- a/net/websockets/websocket_http2_handshake_stream.cc
+++ b/net/websockets/websocket_http2_handshake_stream.cc
@@ -219,8 +219,11 @@
   NOTREACHED();
 }
 
-bool WebSocketHttp2HandshakeStream::GetRemoteEndpoint(IPEndPoint* endpoint) {
-  return session_ && session_->GetRemoteEndpoint(endpoint);
+int WebSocketHttp2HandshakeStream::GetRemoteEndpoint(IPEndPoint* endpoint) {
+  if (!session_)
+    return ERR_SOCKET_NOT_CONNECTED;
+
+  return session_->GetRemoteEndpoint(endpoint);
 }
 
 void WebSocketHttp2HandshakeStream::PopulateNetErrorDetails(
diff --git a/net/websockets/websocket_http2_handshake_stream.h b/net/websockets/websocket_http2_handshake_stream.h
index 341c5210..d0a425a 100644
--- a/net/websockets/websocket_http2_handshake_stream.h
+++ b/net/websockets/websocket_http2_handshake_stream.h
@@ -88,7 +88,7 @@
   bool GetLoadTimingInfo(LoadTimingInfo* load_timing_info) const override;
   void GetSSLInfo(SSLInfo* ssl_info) override;
   void GetSSLCertRequestInfo(SSLCertRequestInfo* cert_request_info) override;
-  bool GetRemoteEndpoint(IPEndPoint* endpoint) override;
+  int GetRemoteEndpoint(IPEndPoint* endpoint) override;
   void Drain(HttpNetworkSession* session) override;
   void SetPriority(RequestPriority priority) override;
   void PopulateNetErrorDetails(NetErrorDetails* details) override;