diff --git a/src/talaria/outbounder.go b/src/talaria/outbounder.go
index 97aac4bc..b1abbb76 100644
--- a/src/talaria/outbounder.go
+++ b/src/talaria/outbounder.go
@@ -53,7 +53,7 @@ type listener struct {
 	requestFactory requestFactory
 }
 
-func (l *listener) OnDeviceEvent(e *device.Event) {
+func (l *listener) onDeviceEvent(e *device.Event) {
 	if e.Type != device.MessageReceived {
 		return
 	}
@@ -65,9 +65,10 @@ func (l *listener) OnDeviceEvent(e *device.Event) {
 	}
 
 	select {
-	case l.outbounds <- outbound:
-	default:
+	case <-outbound.request.Context().Done():
 		l.logger.Error("Dropping outbound message for device [%s]: %s->%s", e.Device.ID(), e.Message.From(), e.Message.To())
+		outbound.cancel()
+	case l.outbounds <- outbound:
 	}
 }
 
@@ -79,7 +80,9 @@ type workerPool struct {
 	transactor func(*http.Request) (*http.Response, error)
 }
 
-func (wp *workerPool) send(outbound *outboundEnvelope) {
+// transact performs all the logic necessary to fulfill and outbound request.
+// This method ensures that the Context associated with the request is properly cancelled.
+func (wp *workerPool) transact(outbound *outboundEnvelope) {
 	defer outbound.cancel()
 
 	response, err := wp.transactor(outbound.request)
@@ -100,7 +103,7 @@ func (wp *workerPool) send(outbound *outboundEnvelope) {
 
 func (wp *workerPool) worker() {
 	for outbound := range wp.outbounds {
-		wp.send(outbound)
+		wp.transact(outbound)
 	}
 }
 
@@ -239,5 +242,5 @@ func (o *Outbounder) Start() device.Listener {
 	)
 
 	workerPool.run(o.WorkerPoolSize)
-	return listener.OnDeviceEvent
+	return listener.onDeviceEvent
 }