diff --git a/client_test.go b/client_test.go
index 7c277e2d9..22495735b 100644
--- a/client_test.go
+++ b/client_test.go
@@ -132,7 +132,9 @@ func TestMain(m *testing.M) {
 			}
 		}
 		if err := cmd.Wait(); err != nil {
-			fmt.Fprintln(os.Stderr, "failed to wait for containerd", err)
+			if _, ok := err.(*exec.ExitError); !ok {
+				fmt.Fprintln(os.Stderr, "failed to wait for containerd", err)
+			}
 		}
 		if err := os.RemoveAll(defaultRoot); err != nil {
 			fmt.Fprintln(os.Stderr, "failed to remove test root dir", err)
diff --git a/linux/runtime.go b/linux/runtime.go
index 43c0b20ed..0430c6943 100644
--- a/linux/runtime.go
+++ b/linux/runtime.go
@@ -211,9 +211,14 @@ func (r *Runtime) Delete(ctx context.Context, c runtime.Task) (*runtime.Exit, er
 	}
 	r.tasks.Delete(ctx, lc)
 
-	bundle := loadBundle(filepath.Join(r.state, namespace, lc.id), filepath.Join(r.root, namespace, lc.id), namespace, r.events)
+	bundle := loadBundle(
+		filepath.Join(r.state, namespace, lc.id),
+		filepath.Join(r.root, namespace, lc.id),
+		namespace,
+		r.events,
+	)
 	if err := bundle.Delete(); err != nil {
-		return nil, err
+		log.G(ctx).WithError(err).Error("failed to delete bundle")
 	}
 	return &runtime.Exit{
 		Status:    rsp.ExitStatus,
diff --git a/linux/shim/client.go b/linux/shim/client.go
index ea634a8f8..2b5016fc5 100644
--- a/linux/shim/client.go
+++ b/linux/shim/client.go
@@ -209,7 +209,18 @@ func (c *Client) KillShim(ctx context.Context) error {
 	if os.Getpid() == pid {
 		return nil
 	}
-	return unix.Kill(pid, unix.SIGKILL)
+	if err := unix.Kill(pid, unix.SIGKILL); err != nil {
+		return err
+	}
+	// wait for shim to die after being SIGKILL'd
+	for {
+		// use kill(pid, 0) here because the shim could have been reparented
+		// and we are no longer able to waitpid(pid, ...) on the shim
+		if err := unix.Kill(pid, 0); err != nil && err == unix.ESRCH {
+			return nil
+		}
+		time.Sleep(10 * time.Millisecond)
+	}
 }
 
 func (c *Client) Close() error {
diff --git a/linux/shim/init.go b/linux/shim/init.go
index 4f4f42933..6777940c8 100644
--- a/linux/shim/init.go
+++ b/linux/shim/init.go
@@ -237,31 +237,33 @@ func (p *initProcess) SetExited(status int) {
 }
 
 func (p *initProcess) Delete(context context.Context) error {
-	status, err := p.Status(context)
-	if err != nil {
-		return err
-	}
-	if status != "stopped" {
-		return fmt.Errorf("cannot delete a running container")
-	}
 	p.killAll(context)
 	p.Wait()
-	err = p.runtime.Delete(context, p.id, nil)
+	err := p.runtime.Delete(context, p.id, nil)
+	// ignore errors if a runtime has already deleted the process
+	// but we still hold metadata and pipes
+	//
+	// this is common during a checkpoint, runc will delete the container state
+	// after a checkpoint and the container will no longer exist within runc
+	if err != nil {
+		if strings.Contains(err.Error(), "does not exist") {
+			err = nil
+		} else {
+			err = p.runtimeError(err, "failed to delete task")
+		}
+	}
 	if p.io != nil {
 		for _, c := range p.closers {
 			c.Close()
 		}
 		p.io.Close()
 	}
-	err = p.runtimeError(err, "OCI runtime delete failed")
-
 	if err2 := mount.UnmountAll(p.rootfs, 0); err2 != nil {
-		log.G(context).WithError(err2).Warn("Failed to cleanup rootfs mount")
+		log.G(context).WithError(err2).Warn("failed to cleanup rootfs mount")
 		if err == nil {
-			err = errors.Wrap(err2, "Failed rootfs umount")
+			err = errors.Wrap(err2, "failed rootfs umount")
 		}
 	}
-
 	return err
 }
 
diff --git a/linux/shim/service.go b/linux/shim/service.go
index be54104dc..7406035a1 100644
--- a/linux/shim/service.go
+++ b/linux/shim/service.go
@@ -147,8 +147,9 @@ func (s *Service) Delete(ctx context.Context, r *google_protobuf.Empty) (*shimap
 		return nil, errdefs.ToGRPCf(errdefs.ErrFailedPrecondition, "container must be created")
 	}
 	p := s.initProcess
-	// TODO (@crosbymichael): how to handle errors here
-	p.Delete(ctx)
+	if err := p.Delete(ctx); err != nil {
+		return nil, err
+	}
 	s.mu.Lock()
 	delete(s.processes, p.ID())
 	s.mu.Unlock()
@@ -178,8 +179,9 @@ func (s *Service) DeleteProcess(ctx context.Context, r *shimapi.DeleteProcessReq
 	if !ok {
 		return nil, errors.Wrapf(errdefs.ErrNotFound, "process %s not found", r.ID)
 	}
-	// TODO (@crosbymichael): how to handle errors here
-	p.Delete(ctx)
+	if err := p.Delete(ctx); err != nil {
+		return nil, err
+	}
 	s.mu.Lock()
 	delete(s.processes, p.ID())
 	s.mu.Unlock()