diff --git a/pkg/deploy/controller.go b/pkg/deploy/controller.go
index 44b0233855..7c999efb31 100644
--- a/pkg/deploy/controller.go
+++ b/pkg/deploy/controller.go
@@ -21,13 +21,18 @@ import (
 	"github.com/rancher/wrangler/pkg/apply"
 	"github.com/rancher/wrangler/pkg/merr"
 	"github.com/rancher/wrangler/pkg/objectset"
+	"github.com/rancher/wrangler/pkg/schemes"
 	"github.com/sirupsen/logrus"
+	corev1 "k8s.io/api/core/v1"
 	"k8s.io/apimachinery/pkg/api/errors"
 	metav1 "k8s.io/apimachinery/pkg/apis/meta/v1"
 	"k8s.io/apimachinery/pkg/apis/meta/v1/unstructured"
 	"k8s.io/apimachinery/pkg/runtime"
 	"k8s.io/apimachinery/pkg/runtime/schema"
 	yamlDecoder "k8s.io/apimachinery/pkg/util/yaml"
+	"k8s.io/client-go/kubernetes"
+	typedcorev1 "k8s.io/client-go/kubernetes/typed/core/v1"
+	"k8s.io/client-go/tools/record"
 )
 
 const (
@@ -36,7 +41,7 @@ const (
 )
 
 // WatchFiles sets up an OnChange callback to start a periodic goroutine to watch files for changes once the controller has started up.
-func WatchFiles(ctx context.Context, apply apply.Apply, addons controllersv1.AddonController, disables map[string]bool, bases ...string) error {
+func WatchFiles(ctx context.Context, client kubernetes.Interface, apply apply.Apply, addons controllersv1.AddonController, disables map[string]bool, bases ...string) error {
 	w := &watcher{
 		apply:      apply,
 		addonCache: addons.Cache(),
@@ -49,7 +54,7 @@ func WatchFiles(ctx context.Context, apply apply.Apply, addons controllersv1.Add
 	addons.Enqueue(metav1.NamespaceNone, startKey)
 	addons.OnChange(ctx, "addon-start", func(key string, _ *apisv1.Addon) (*apisv1.Addon, error) {
 		if key == startKey {
-			go w.start(ctx)
+			go w.start(ctx, client)
 		}
 		return nil, nil
 	})
@@ -64,10 +69,17 @@ type watcher struct {
 	bases      []string
 	disables   map[string]bool
 	modTime    map[string]time.Time
+	recorder   record.EventRecorder
 }
 
 // start calls listFiles at regular intervals to trigger application of manifests that have changed on disk.
-func (w *watcher) start(ctx context.Context) {
+func (w *watcher) start(ctx context.Context, client kubernetes.Interface) {
+	nodeName := os.Getenv("NODE_NAME")
+	broadcaster := record.NewBroadcaster()
+	broadcaster.StartLogging(logrus.Infof)
+	broadcaster.StartRecordingToSink(&typedcorev1.EventSinkImpl{Interface: client.CoreV1().Events(metav1.NamespaceSystem)})
+	w.recorder = broadcaster.NewRecorder(schemes.All, corev1.EventSource{Component: ControllerName, Host: nodeName})
+
 	force := true
 	for {
 		if err := w.listFiles(force); err == nil {
@@ -153,14 +165,28 @@ func (w *watcher) listFilesIn(base string, force bool) error {
 // deploy loads yaml from a manifest on disk, creates an AddOn resource to track its application, and then applies
 // all resources contained within to the cluster.
 func (w *watcher) deploy(path string, compareChecksum bool) error {
-	content, err := ioutil.ReadFile(path)
+	name := basename(path)
+	addon, err := w.getOrCreateAddon(name)
 	if err != nil {
 		return err
 	}
 
-	name := basename(path)
-	addon, err := w.getOrCreateAddon(name)
+	addon.Spec.Source = path
+	addon.Status.GVKs = nil
+
+	// Create the new Addon now so that we can use it to report Events when parsing/applying the manifest
+	// Events need the UID and ObjectRevision set to function properly
+	if addon.UID == "" {
+		newAddon, err := w.addons.Create(&addon)
+		if err != nil {
+			return err
+		}
+		addon = *newAddon
+	}
+
+	content, err := ioutil.ReadFile(path)
 	if err != nil {
+		w.recorder.Eventf(&addon, corev1.EventTypeWarning, "ReadManifestFailed", "Read manifest at %q failed: %v", path, err)
 		return err
 	}
 
@@ -170,26 +196,24 @@ func (w *watcher) deploy(path string, compareChecksum bool) error {
 		return nil
 	}
 
+	// Attempt to parse the YAML/JSON into objects. Failure at this point would be due to bad file content - not YAML/JSON,
+	// YAML/JSON that can't be converted to Kubernetes objects, etc.
 	objectSet, err := objectSet(content)
 	if err != nil {
+		w.recorder.Eventf(&addon, corev1.EventTypeWarning, "ParseManifestFailed", "Parse manifest at %q failed: %v", path, err)
 		return err
 	}
 
+	// Attempt to apply the changes. Failure at this point would be due to more complicated issues - invalid changes to
+	// existing objects, rejected by validating webhooks, etc.
+	w.recorder.Eventf(&addon, corev1.EventTypeNormal, "ApplyingManifest", "Applying manifest at %q", path)
 	if err := w.apply.WithOwner(&addon).Apply(objectSet); err != nil {
+		w.recorder.Eventf(&addon, corev1.EventTypeWarning, "ApplyManifestFailed", "Applying manifest at %q failed: %v", path, err)
 		return err
 	}
 
-	addon.Spec.Source = path
-	addon.Spec.Checksum = checksum
-	addon.Status.GVKs = nil
-
-	// Create the new Addon now so that we can use it to report Events when parsing/applying the manifest
-	// Events need the UID and ObjectRevision set to function properly
-	if addon.UID == "" {
-		_, err := w.addons.Create(&addon)
-		return err
-	}
-
+	// Emit event, Update Addon checksum and modtime only if apply was successful
+	w.recorder.Eventf(&addon, corev1.EventTypeNormal, "AppliedManifest", "Applied manifest at %q", path)
 	_, err = w.addons.Update(&addon)
 	return err
 }
@@ -203,24 +227,29 @@ func (w *watcher) delete(path string) error {
 		return err
 	}
 
-	// ensure that the addon is completely removed before deleting the objectSet,
-	// so return when err == nil, otherwise pods may get stuck terminating
-	if err := w.addons.Delete(addon.Namespace, addon.Name, &metav1.DeleteOptions{}); err == nil || !errors.IsNotFound(err) {
-		return err
-	}
-
 	content, err := ioutil.ReadFile(path)
 	if err != nil {
+		w.recorder.Eventf(&addon, corev1.EventTypeWarning, "ReadManifestFailed", "Read manifest at %q failed: %v", path, err)
 		return err
 	}
+
 	objectSet, err := objectSet(content)
 	if err != nil {
+		w.recorder.Eventf(&addon, corev1.EventTypeWarning, "ParseManifestFailed", "Parse manifest at %q failed: %v", path, err)
 		return err
 	}
 	var gvk []schema.GroupVersionKind
 	for k := range objectSet.ObjectsByGVK() {
 		gvk = append(gvk, k)
 	}
+
+	// ensure that the addon is completely removed before deleting the objectSet,
+	// so return when err == nil, otherwise pods may get stuck terminating
+	w.recorder.Eventf(&addon, corev1.EventTypeNormal, "DeletingManifest", "Deleting manifest at %q", path)
+	if err := w.addons.Delete(addon.Namespace, addon.Name, &metav1.DeleteOptions{}); err == nil || !errors.IsNotFound(err) {
+		return err
+	}
+
 	// apply an empty set with owner & gvk data to delete
 	if err := w.apply.WithOwner(&addon).WithGVK(gvk...).Apply(nil); err != nil {
 		return err
diff --git a/pkg/server/server.go b/pkg/server/server.go
index ead447c57c..c20a1485ab 100644
--- a/pkg/server/server.go
+++ b/pkg/server/server.go
@@ -248,6 +248,7 @@ func stageFiles(ctx context.Context, sc *Context, controlConfig *config.Control)
 	}
 
 	return deploy.WatchFiles(ctx,
+		sc.K8s,
 		sc.Apply,
 		sc.K3s.K3s().V1().Addon(),
 		controlConfig.Disables,