diff --git a/go/vt/vitessdriver/driver.go b/go/vt/vitessdriver/driver.go
index 63c00ab730e..66f6e52528b 100644
--- a/go/vt/vitessdriver/driver.go
+++ b/go/vt/vitessdriver/driver.go
@@ -209,6 +209,15 @@ func (c *conn) dial() error {
 	return nil
 }
 
+func (c *conn) Ping(ctx context.Context) error {
+	if c.Streaming {
+		return errors.New("Ping not allowed for streaming connections")
+	}
+
+	_, err := c.ExecContext(ctx, "select 1", nil)
+	return err
+}
+
 func (c *conn) Prepare(query string) (driver.Stmt, error) {
 	return &stmt{c: c, query: query}, nil
 }
diff --git a/go/vt/vtadmin/vtsql/config.go b/go/vt/vtadmin/vtsql/config.go
index 285925c5959..8655bfd7c9f 100644
--- a/go/vt/vtadmin/vtsql/config.go
+++ b/go/vt/vtadmin/vtsql/config.go
@@ -18,6 +18,7 @@ package vtsql
 
 import (
 	"fmt"
+	"time"
 
 	"github.com/spf13/pflag"
 
@@ -34,6 +35,8 @@ type Config struct {
 	DiscoveryTags []string
 	Credentials   Credentials
 
+	DialPingTimeout time.Duration
+
 	// CredentialsPath is used only to power vtadmin debug endpoints; there may
 	// be a better way where we don't need to put this in the config, because
 	// it's not really an "option" in normal use.
@@ -65,6 +68,8 @@ func Parse(cluster *vtadminpb.Cluster, disco discovery.Discovery, args []string)
 func (c *Config) Parse(args []string) error {
 	fs := pflag.NewFlagSet("", pflag.ContinueOnError)
 
+	fs.DurationVar(&c.DialPingTimeout, "dial-ping-timeout", time.Millisecond*500,
+		"Timeout to use when pinging an existing connection during calls to Dial.")
 	fs.StringSliceVar(&c.DiscoveryTags, "discovery-tags", []string{},
 		"repeated, comma-separated list of tags to use when discovering a vtgate to connect to. "+
 			"the semantics of the tags may depend on the specific discovery implementation used")
diff --git a/go/vt/vtadmin/vtsql/config_test.go b/go/vt/vtadmin/vtsql/config_test.go
index e32b6855a4f..84f877f234a 100644
--- a/go/vt/vtadmin/vtsql/config_test.go
+++ b/go/vt/vtadmin/vtsql/config_test.go
@@ -23,6 +23,7 @@ import (
 	"path/filepath"
 	"strings"
 	"testing"
+	"time"
 
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
@@ -143,6 +144,7 @@ func TestConfigParse(t *testing.T) {
 				Id:   "cid",
 				Name: "testcluster",
 			},
+			DialPingTimeout: time.Millisecond * 500,
 			DiscoveryTags:   expectedTags,
 			Credentials:     expectedCreds,
 			CredentialsPath: path,
diff --git a/go/vt/vtadmin/vtsql/vtsql.go b/go/vt/vtadmin/vtsql/vtsql.go
index 6a1b9b3c82c..c5fe327ec49 100644
--- a/go/vt/vtadmin/vtsql/vtsql.go
+++ b/go/vt/vtadmin/vtsql/vtsql.go
@@ -21,11 +21,13 @@ import (
 	"database/sql"
 	"errors"
 	"fmt"
+	"time"
 
 	"google.golang.org/grpc"
 
 	"vitess.io/vitess/go/trace"
 	"vitess.io/vitess/go/vt/callerid"
+	"vitess.io/vitess/go/vt/log"
 	"vitess.io/vitess/go/vt/vitessdriver"
 	"vitess.io/vitess/go/vt/vtadmin/cluster/discovery"
 	"vitess.io/vitess/go/vt/vtadmin/vtadminproto"
@@ -71,7 +73,8 @@ type VTGateProxy struct {
 	// DialFunc is called to open a new database connection. In production this
 	// should always be vitessdriver.OpenWithConfiguration, but it is exported
 	// for testing purposes.
-	DialFunc func(cfg vitessdriver.Configuration) (*sql.DB, error)
+	DialFunc        func(cfg vitessdriver.Configuration) (*sql.DB, error)
+	dialPingTimeout time.Duration
 
 	host string
 	conn *sql.DB
@@ -96,11 +99,12 @@ func New(cfg *Config) *VTGateProxy {
 	}
 
 	return &VTGateProxy{
-		cluster:       cfg.Cluster,
-		discovery:     cfg.Discovery,
-		discoveryTags: discoveryTags,
-		creds:         cfg.Credentials,
-		DialFunc:      vitessdriver.OpenWithConfiguration,
+		cluster:         cfg.Cluster,
+		discovery:       cfg.Discovery,
+		discoveryTags:   discoveryTags,
+		creds:           cfg.Credentials,
+		DialFunc:        vitessdriver.OpenWithConfiguration,
+		dialPingTimeout: cfg.DialPingTimeout,
 	}
 }
 
@@ -132,13 +136,27 @@ func (vtgate *VTGateProxy) Dial(ctx context.Context, target string, opts ...grpc
 	vtgate.annotateSpan(span)
 
 	if vtgate.conn != nil {
-		span.Annotate("is_noop", true)
-
-		// (TODO:@amason): consider a quick Ping() check in this case, and get a
-		// new connection if that fails.
-		return nil
+		ctx, cancel := context.WithTimeout(ctx, vtgate.dialPingTimeout)
+		defer cancel()
+
+		err := vtgate.PingContext(ctx)
+		switch err {
+		case nil:
+			log.Infof("Have valid connection to %s, reusing it.", vtgate.host)
+			span.Annotate("is_noop", true)
+
+			return nil
+		default:
+			log.Warningf("Ping failed on host %s: %s; Rediscovering a vtgate to get new connection", vtgate.host, err)
+
+			if err := vtgate.Close(); err != nil {
+				log.Warningf("Error when closing connection to vtgate %s: %s; Continuing anyway ...", vtgate.host, err)
+			}
+		}
 	}
 
+	span.Annotate("is_noop", false)
+
 	if vtgate.host == "" {
 		gate, err := vtgate.discovery.DiscoverVTGateAddr(ctx, vtgate.discoveryTags)
 		if err != nil {
@@ -150,6 +168,8 @@ func (vtgate *VTGateProxy) Dial(ctx context.Context, target string, opts ...grpc
 		span.Annotate("vtgate_host", gate)
 	}
 
+	log.Infof("Dialing %s ...", vtgate.host)
+
 	conf := vitessdriver.Configuration{
 		Protocol:        fmt.Sprintf("grpc_%s", vtgate.cluster.Id),
 		Address:         vtgate.host,
diff --git a/go/vt/vtadmin/vtsql/vtsql_test.go b/go/vt/vtadmin/vtsql/vtsql_test.go
index 17c1b503398..c0ddd84e170 100644
--- a/go/vt/vtadmin/vtsql/vtsql_test.go
+++ b/go/vt/vtadmin/vtsql/vtsql_test.go
@@ -20,6 +20,7 @@ import (
 	"context"
 	"database/sql"
 	"testing"
+	"time"
 
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
@@ -100,8 +101,9 @@ func TestDial(t *testing.T) {
 		{
 			name: "existing conn",
 			proxy: &VTGateProxy{
-				cluster: &vtadminpb.Cluster{},
-				conn:    sql.OpenDB(&fakevtsql.Connector{}),
+				cluster:         &vtadminpb.Cluster{},
+				conn:            sql.OpenDB(&fakevtsql.Connector{}),
+				dialPingTimeout: time.Millisecond * 10,
 			},
 			shouldErr: false,
 		},