diff --git a/runtime/v2/shim.go b/runtime/v2/shim.go
index 0fc94e80e..86d2e40d6 100644
--- a/runtime/v2/shim.go
+++ b/runtime/v2/shim.go
@@ -29,8 +29,8 @@ import (
 
 	"github.com/containerd/ttrpc"
 	"github.com/hashicorp/go-multierror"
-	"github.com/sirupsen/logrus"
 	"google.golang.org/grpc"
+	"google.golang.org/grpc/connectivity"
 	"google.golang.org/grpc/credentials/insecure"
 
 	eventstypes "github.com/containerd/containerd/api/events"
@@ -221,7 +221,7 @@ func makeConnection(ctx context.Context, address string, onClose func()) (_ io.C
 		params.Protocol = "ttrpc"
 	}
 
-	log.G(ctx).WithFields(logrus.Fields{
+	log.G(ctx).WithFields(log.Fields{
 		"address":  params.Address,
 		"protocol": params.Protocol,
 	}).Debug("shim bootstrap parameters")
@@ -238,38 +238,78 @@ func makeConnection(ctx context.Context, address string, onClose func()) (_ io.C
 			}
 		}()
 
-		ttrpcClient := ttrpc.NewClient(conn, ttrpc.WithOnClose(onClose))
-		defer func() {
-			if retErr != nil {
-				ttrpcClient.Close()
-			}
-		}()
-
-		return ttrpcClient, nil
+		return ttrpc.NewClient(conn, ttrpc.WithOnClose(onClose)), nil
 	case "grpc":
+		ctx, cancel := context.WithTimeout(ctx, time.Second*100)
+		defer cancel()
+
 		gopts := []grpc.DialOption{
 			grpc.WithTransportCredentials(insecure.NewCredentials()),
+			grpc.WithBlock(),
 		}
-
-		conn, err := grpc.DialContext(ctx, dialer.DialAddress(params.Address), gopts...)
-		if err != nil {
-			return nil, fmt.Errorf("failed to create GRPC connection: %w", err)
-		}
-
-		defer func() {
-			if retErr != nil {
-				conn.Close()
-			}
-		}()
-
-		// TODO: figure out how to invoke onCloseWithShimLog callback when shim connection is closed.
-
-		return conn, nil
+		return grpcDialContext(ctx, dialer.DialAddress(params.Address), onClose, gopts...)
 	default:
 		return nil, fmt.Errorf("unexpected protocol: %q", params.Protocol)
 	}
 }
 
+// grpcDialContext and the underlying grpcConn type exist solely
+// so we can have something similar to ttrpc.WithOnClose to have
+// a callback run when the connection is severed or explicitly closed.
+func grpcDialContext(
+	ctx context.Context,
+	target string,
+	onClose func(),
+	gopts ...grpc.DialOption,
+) (*grpcConn, error) {
+	client, err := grpc.DialContext(ctx, target, gopts...)
+	if err != nil {
+		return nil, fmt.Errorf("failed to create GRPC connection: %w", err)
+	}
+
+	done := make(chan struct{})
+	go func() {
+		gctx := context.Background()
+		sourceState := connectivity.Ready
+		for {
+			if client.WaitForStateChange(gctx, sourceState) {
+				state := client.GetState()
+				if state == connectivity.Idle || state == connectivity.Shutdown {
+					break
+				}
+				// Could be transient failure. Lets see if we can get back to a working
+				// state.
+				log.G(gctx).WithFields(log.Fields{
+					"state": state,
+					"addr":  target,
+				}).Warn("shim grpc connection unexpected state")
+				sourceState = state
+			}
+		}
+		onClose()
+		close(done)
+	}()
+
+	return &grpcConn{
+		ClientConn:  client,
+		onCloseDone: done,
+	}, nil
+}
+
+type grpcConn struct {
+	*grpc.ClientConn
+	onCloseDone chan struct{}
+}
+
+func (gc *grpcConn) UserOnCloseWait(ctx context.Context) error {
+	select {
+	case <-gc.onCloseDone:
+		return nil
+	case <-ctx.Done():
+		return ctx.Err()
+	}
+}
+
 type shim struct {
 	bundle *Bundle
 	client any
@@ -300,6 +340,10 @@ func (s *shim) Close() error {
 		return ttrpcClient.Close()
 	}
 
+	if grpcClient, ok := s.client.(*grpcConn); ok {
+		return grpcClient.Close()
+	}
+
 	return nil
 }
 
@@ -318,6 +362,16 @@ func (s *shim) Delete(ctx context.Context) error {
 		}
 	}
 
+	if grpcClient, ok := s.client.(*grpcConn); ok {
+		if err := grpcClient.Close(); err != nil {
+			result = multierror.Append(result, fmt.Errorf("failed to close grpc client: %w", err))
+		}
+
+		if err := grpcClient.UserOnCloseWait(ctx); err != nil {
+			result = multierror.Append(result, fmt.Errorf("close wait error: %w", err))
+		}
+	}
+
 	if err := s.bundle.Delete(); err != nil {
 		log.G(ctx).WithField("id", s.ID()).WithError(err).Error("failed to delete bundle")
 		result = multierror.Append(result, fmt.Errorf("failed to delete bundle: %w", err))