diff --git a/CHANGES b/CHANGES
index 16463e3cb25..cec55b67025 100644
--- a/CHANGES
+++ b/CHANGES
@@ -1,6 +1,8 @@
                                                          -*- coding: utf-8 -*-
 Changes with Apache Traffic Server 5.0.0
 
+  *) [TS-2584] Fix failed assert transforming and caching negative responses
+
   *) [TS-2582] Make traffic_cop debugging eadier by logging to stdout.
 
   *) [TS-2579] Remove ipv4 limit for FetchSM and TSFetchUrl/TSFetchPages.
diff --git a/plugins/experimental/metalink/test/negativeCaching b/plugins/experimental/metalink/test/negativeCaching
new file mode 100755
index 00000000000..59466572b10
--- /dev/null
+++ b/plugins/experimental/metalink/test/negativeCaching
@@ -0,0 +1,72 @@
+#!/usr/bin/env python
+
+print '''1..1 negativeCaching
+# Negative caching doesn't crash the proxy'''
+
+from twisted.internet import error, protocol, reactor, tcp
+from twisted.web import http
+
+def callback():
+  print 'not ok 1 - Why didn\'t the test finish yet?'
+
+  reactor.stop()
+
+reactor.callLater(1, callback)
+
+class factory(http.HTTPFactory):
+  class protocol(http.HTTPChannel):
+    class requestFactory(http.Request):
+      def requestReceived(ctx, method, target, version):
+
+        ctx.client = None
+        ctx.clientproto = version
+
+        ctx.setResponseCode(404)
+
+        # Don't send a Content-Length header or a final chunk because
+        # HttpTunnel::producer_run() sends an HTTP_TUNNEL_EVENT_PRECOMPLETE
+        # event at the end of the content which causes
+        # HttpSM::tunnel_handler_server() to turn off negative caching.
+        #
+        # Write some content to reach
+        # ink_assert(cache_info->response_get()->valid()) in
+        # HttpTransact::set_headers_for_cache_write().  It's called when
+        # TransformTerminus sends a TRANSFORM_READ_READY event, but the
+        # Metalink transform only reenabled TransformTerminus at the end of the
+        # content or if more content was available.
+        ctx.write('negativeCaching')
+
+server = tcp.Port(0, factory())
+server.startListening()
+
+print '# Listening on {0}:{1}'.format(*server.socket.getsockname())
+
+class factory(protocol.ClientFactory):
+  def clientConnectionFailed(ctx, connector, reason):
+
+    print 'Bail out!'
+    reason.printTraceback()
+
+    reactor.stop()
+
+  class protocol(http.HTTPClient):
+    def connectionLost(ctx, reason):
+      try:
+        reactor.stop()
+
+      except error.ReactorNotRunning:
+        pass
+
+      else:
+        print 'not ok 1 - Did the proxy crash?  (The client connection closed.)'
+
+    connectionMade = lambda ctx: ctx.transport.write('GET {0}:{1} HTTP/1.1\r\n\r\n'.format(*server.socket.getsockname()))
+
+    def handleStatus(ctx, version, status, message):
+      print 'ok 1 - The proxy didn\'t crash (got a reasponse status)'
+
+      reactor.stop()
+
+tcp.Connector('localhost', 8080, factory(), 30, None, reactor).connect()
+
+reactor.run()
diff --git a/proxy/http/HttpTransact.cc b/proxy/http/HttpTransact.cc
index 9692d998a2d..fb16688a2e8 100644
--- a/proxy/http/HttpTransact.cc
+++ b/proxy/http/HttpTransact.cc
@@ -4783,6 +4783,11 @@ HttpTransact::set_headers_for_cache_write(State* s, HTTPInfo* cache_info, HTTPHd
 
   if (!cache_info->valid()) {
     cache_info->create();
+    cache_info->response_set(response);
+  } else if (!s->negative_caching) {
+    cache_info->response_set(response);
+  } else {
+    ink_assert(cache_info->response_get()->valid());
   }
 
   /* Store the requested URI */
@@ -4805,11 +4810,6 @@ HttpTransact::set_headers_for_cache_write(State* s, HTTPInfo* cache_info, HTTPHd
     request->url_set(s->hdr_info.client_request.url_get());
   }
   cache_info->request_set(request);
-  if (!s->negative_caching)
-    cache_info->response_set(response);
-  else {
-    ink_assert(cache_info->response_get()->valid());
-  }
 
   if (s->api_server_request_body_set)
     cache_info->request_get()->method_set(HTTP_METHOD_GET, HTTP_LEN_GET);