diff --git a/proxy/proxy.go b/proxy/proxy.go
index 81d8e79c..dc6bcfcf 100644
--- a/proxy/proxy.go
+++ b/proxy/proxy.go
@@ -59,7 +59,8 @@ type Config struct {
 
 type wait struct {
 	ident string
-	ch    chan struct{}
+	ch    chan error
+	done  bool
 }
 
 type Proxy struct {
@@ -296,19 +297,17 @@ func (proxy *Proxy) listen(protoAndAddr string) (net.Listener, string, error) {
 // weavedocker.ContainerObserver interface
 func (proxy *Proxy) ContainerStarted(ident string) {
 	container, err := proxy.client.InspectContainer(ident)
-	if err != nil {
-		if _, ok := err.(*docker.NoSuchContainer); !ok {
-			Log.Warningf("unable to attach new container %s since inspecting it failed: %v", ident, err)
+	if err == nil {
+		if containerShouldAttach(container) {
+			err = proxy.attach(container, true)
+		} else if containerIsWeaveRouter(container) {
+			err = proxy.attachRouter(container)
 		}
-		return
 	}
-	// If this was a container we modified the entrypoint for, attach it to the network
-	if containerShouldAttach(container) {
-		proxy.attach(container, true)
-	} else if containerIsWeaveRouter(container) {
-		proxy.attachRouter(container)
+	if _, ok := err.(*docker.NoSuchContainer); err != nil && !ok {
+		Log.Warningf("unable to attach new container %s since inspecting it failed: %v", ident, err)
 	}
-	proxy.notifyWaiters(container.ID)
+	proxy.notifyWaiters(ident, err)
 }
 
 func containerShouldAttach(container *docker.Container) bool {
@@ -321,8 +320,7 @@ func containerIsWeaveRouter(container *docker.Container) bool {
 
 func (proxy *Proxy) createWait(r *http.Request, ident string) {
 	proxy.Lock()
-	ch := make(chan struct{})
-	proxy.waiters[r] = &wait{ident: ident, ch: ch}
+	proxy.waiters[r] = &wait{ident: ident, ch: make(chan error, 1)}
 	proxy.Unlock()
 }
 
@@ -332,19 +330,20 @@ func (proxy *Proxy) removeWait(r *http.Request) {
 	proxy.Unlock()
 }
 
-func (proxy *Proxy) notifyWaiters(ident string) {
+func (proxy *Proxy) notifyWaiters(ident string, err error) {
 	proxy.Lock()
 	for _, wait := range proxy.waiters {
-		if ident == wait.ident && wait.ch != nil {
+		if ident == wait.ident && !wait.done {
+			wait.ch <- err
 			close(wait.ch)
-			wait.ch = nil
+			wait.done = true
 		}
 	}
 	proxy.Unlock()
 }
 
-func (proxy *Proxy) waitForStart(r *http.Request) {
-	var ch chan struct{}
+func (proxy *Proxy) waitForStart(r *http.Request) error {
+	var ch chan error
 	proxy.Lock()
 	wait, found := proxy.waiters[r]
 	if found {
@@ -353,8 +352,9 @@ func (proxy *Proxy) waitForStart(r *http.Request) {
 	proxy.Unlock()
 	if ch != nil {
 		Log.Debugf("Wait for start of container %s", wait.ident)
-		<-ch
+		return <-ch
 	}
+	return nil
 }
 
 func (proxy *Proxy) ContainerDied(ident string) {
diff --git a/proxy/start_container_interceptor.go b/proxy/start_container_interceptor.go
index 1d0d17df..e182a629 100644
--- a/proxy/start_container_interceptor.go
+++ b/proxy/start_container_interceptor.go
@@ -53,6 +53,5 @@ func (i *startContainerInterceptor) InterceptResponse(r *http.Response) error {
 	if r.StatusCode < 200 || r.StatusCode >= 300 { // Docker didn't do the start
 		return nil
 	}
-	i.proxy.waitForStart(r.Request)
-	return nil
+	return i.proxy.waitForStart(r.Request)
 }
diff --git a/test/695_proxy_failure_modes_test.sh b/test/695_proxy_failure_modes_test.sh
new file mode 100755
index 00000000..45679ae4
--- /dev/null
+++ b/test/695_proxy_failure_modes_test.sh
@@ -0,0 +1,12 @@
+#! /bin/bash
+
+. ./config.sh
+
+start_suite "Proxy failure modes"
+
+# docker run should fail when weave router is not running
+weave_on $HOST1 launch-proxy
+assert_raises "proxy docker_on $HOST1 run --rm $SMALL_IMAGE true" 1
+assert_raises "proxy docker_on $HOST1 run --rm $SMALL_IMAGE true 2>&1 1>/dev/null | grep 'Error response from daemon: weave container is not present. Have you launched it?'"
+
+end_suite