diff --git a/mdm/checkin.go b/mdm/checkin.go
index 0b996957..b11adbb0 100644
--- a/mdm/checkin.go
+++ b/mdm/checkin.go
@@ -27,6 +27,12 @@ func (svc *MDMService) Checkin(ctx context.Context, event CheckinEvent) error {
 		return errors.Wrap(err, "get checkin topic from message")
 	}
 
+	if topic == AuthenticateTopic {
+		if err := svc.queue.Clear(ctx, event); err != nil {
+			return errors.Wrap(err, "clearing queue on enrollment attempt")
+		}
+	}
+
 	err = svc.pub.Publish(ctx, topic, msg)
 	return errors.Wrapf(err, "publish checkin on topic: %s", topic)
 }
diff --git a/mdm/service.go b/mdm/service.go
index d71fa3c5..64958ebd 100644
--- a/mdm/service.go
+++ b/mdm/service.go
@@ -23,6 +23,7 @@ const (
 // Queue is an MDM Command Queue.
 type Queue interface {
 	Next(context.Context, Response) ([]byte, error)
+	Clear(context.Context, CheckinEvent) error
 }
 
 type MDMService struct {
diff --git a/platform/queue/queue.go b/platform/queue/queue.go
index a45d1766..298bdc13 100644
--- a/platform/queue/queue.go
+++ b/platform/queue/queue.go
@@ -54,6 +54,28 @@ func (db *Store) Next(ctx context.Context, resp mdm.Response) ([]byte, error) {
 	return cmd.Payload, nil
 }
 
+func (db *Store) Clear(ctx context.Context, event mdm.CheckinEvent) error {
+	udid := event.Command.UDID
+	if event.Command.UserID != "" {
+		udid = event.Command.UserID
+	}
+	if event.Command.EnrollmentID != "" {
+		udid = event.Command.EnrollmentID
+	}
+
+	dc, err := db.DeviceCommand(udid)
+	if isNotFound(err) {
+		return nil
+	} else if err != nil {
+		return errors.Wrapf(err, "get device to clear queue, udid: %s", udid)
+	}
+
+	dc.Commands = nil
+	dc.NotNow = nil
+
+	return db.Save(dc)
+}
+
 func (db *Store) nextCommand(ctx context.Context, resp mdm.Response) (*Command, error) {
 	// The UDID is the primary key for the queue.
 	// Depending on the enrollment type, replace the UDID with a different ID type.