diff --git a/pkg/sql/colflow/colrpc/colrpc_test.go b/pkg/sql/colflow/colrpc/colrpc_test.go
index 22cad5c56d5a..d924f85a92e1 100644
--- a/pkg/sql/colflow/colrpc/colrpc_test.go
+++ b/pkg/sql/colflow/colrpc/colrpc_test.go
@@ -642,7 +642,8 @@ func TestOutboxStreamIDPropagation(t *testing.T) {
 			roachpb.NodeID(0),
 			execinfrapb.FlowID{UUID: uuid.MakeV4()},
 			outboxStreamID,
-			nil,
+			nil, /* cancelFn */
+			0,   /* connectionTimeout */
 		)
 		outboxDone <- struct{}{}
 	}()
diff --git a/pkg/sql/colflow/colrpc/outbox.go b/pkg/sql/colflow/colrpc/outbox.go
index 85d13ba946c7..ec4acab0d34f 100644
--- a/pkg/sql/colflow/colrpc/outbox.go
+++ b/pkg/sql/colflow/colrpc/outbox.go
@@ -15,21 +15,21 @@ import (
 	"context"
 	"io"
 	"sync/atomic"
+	"time"
 
 	"github.com/cockroachdb/cockroach/pkg/col/coldata"
 	"github.com/cockroachdb/cockroach/pkg/col/colserde"
 	"github.com/cockroachdb/cockroach/pkg/roachpb"
-	"github.com/cockroachdb/cockroach/pkg/rpc"
 	"github.com/cockroachdb/cockroach/pkg/sql/colexec"
 	"github.com/cockroachdb/cockroach/pkg/sql/colexecbase"
 	"github.com/cockroachdb/cockroach/pkg/sql/colexecbase/colexecerror"
 	"github.com/cockroachdb/cockroach/pkg/sql/colmem"
+	"github.com/cockroachdb/cockroach/pkg/sql/execinfra"
 	"github.com/cockroachdb/cockroach/pkg/sql/execinfrapb"
 	"github.com/cockroachdb/cockroach/pkg/sql/types"
 	"github.com/cockroachdb/cockroach/pkg/util/log"
 	"github.com/cockroachdb/errors"
 	"github.com/cockroachdb/logtags"
-	"google.golang.org/grpc"
 )
 
 // flowStreamClient is a utility interface used to mock out the RPC layer.
@@ -39,13 +39,6 @@ type flowStreamClient interface {
 	CloseSend() error
 }
 
-// Dialer is used for dialing based on node IDs. It extracts out the single
-// method that Outbox.Run needs from nodedialer.Dialer so that we can mock it
-// in tests outside of this package.
-type Dialer interface {
-	Dial(context.Context, roachpb.NodeID, rpc.ConnectionClass) (*grpc.ClientConn, error)
-}
-
 // Outbox is used to push data from local flows to a remote endpoint. Run may
 // be called with the necessary information to establish a connection to a
 // given remote endpoint.
@@ -130,11 +123,12 @@ func (o *Outbox) close(ctx context.Context) {
 //    Outbox goes through the same steps as 1).
 func (o *Outbox) Run(
 	ctx context.Context,
-	dialer Dialer,
+	dialer execinfra.Dialer,
 	nodeID roachpb.NodeID,
 	flowID execinfrapb.FlowID,
 	streamID execinfrapb.StreamID,
 	cancelFn context.CancelFunc,
+	connectionTimeout time.Duration,
 ) {
 	o.runnerCtx = ctx
 	ctx = logtags.AddTag(ctx, "streamID", streamID)
@@ -142,7 +136,7 @@ func (o *Outbox) Run(
 
 	var stream execinfrapb.DistSQL_FlowStreamClient
 	if err := func() error {
-		conn, err := dialer.Dial(ctx, nodeID, rpc.DefaultClass)
+		conn, err := execinfra.GetConnForOutbox(ctx, dialer, nodeID, connectionTimeout)
 		if err != nil {
 			log.Warningf(
 				ctx,
diff --git a/pkg/sql/colflow/vectorized_flow.go b/pkg/sql/colflow/vectorized_flow.go
index 52d824164f63..fa71db13ad23 100644
--- a/pkg/sql/colflow/vectorized_flow.go
+++ b/pkg/sql/colflow/vectorized_flow.go
@@ -586,7 +586,15 @@ func (s *vectorizedFlowCreator) setupRemoteOutputStream(
 		// derive a separate child context for each outbox.
 		var outboxCancelFn context.CancelFunc
 		ctx, outboxCancelFn = context.WithCancel(ctx)
-		outbox.Run(ctx, s.nodeDialer, stream.TargetNodeID, s.flowID, stream.StreamID, outboxCancelFn)
+		outbox.Run(
+			ctx,
+			s.nodeDialer,
+			stream.TargetNodeID,
+			s.flowID,
+			stream.StreamID,
+			outboxCancelFn,
+			flowinfra.SettingFlowStreamTimeout.Get(&flowCtx.Cfg.Settings.SV),
+		)
 		currentOutboxes := atomic.AddInt32(&s.numOutboxes, -1)
 		// When the last Outbox on this node exits, we want to make sure that
 		// everything is shutdown; namely, we need to call cancelFn if:
diff --git a/pkg/sql/colflow/vectorized_flow_shutdown_test.go b/pkg/sql/colflow/vectorized_flow_shutdown_test.go
index 6fe06540055e..e167e1e15169 100644
--- a/pkg/sql/colflow/vectorized_flow_shutdown_test.go
+++ b/pkg/sql/colflow/vectorized_flow_shutdown_test.go
@@ -258,7 +258,15 @@ func TestVectorizedFlowShutdown(t *testing.T) {
 					require.NoError(t, err)
 					wg.Add(1)
 					go func(id int) {
-						outbox.Run(ctx, dialer, execinfra.StaticNodeID, flowID, execinfrapb.StreamID(id), cancelFn)
+						outbox.Run(
+							ctx,
+							dialer,
+							execinfra.StaticNodeID,
+							flowID,
+							execinfrapb.StreamID(id),
+							cancelFn,
+							0, /* connectionTimeout */
+						)
 						wg.Done()
 					}(id)
 
diff --git a/pkg/sql/execinfra/outboxbase.go b/pkg/sql/execinfra/outboxbase.go
new file mode 100644
index 000000000000..d0ce09c6626f
--- /dev/null
+++ b/pkg/sql/execinfra/outboxbase.go
@@ -0,0 +1,53 @@
+// Copyright 2020 The Cockroach Authors.
+//
+// Use of this software is governed by the Business Source License
+// included in the file licenses/BSL.txt.
+//
+// As of the Change Date specified in that file, in accordance with
+// the Business Source License, use of this software will be governed
+// by the Apache License, Version 2.0, included in the file
+// licenses/APL.txt.
+
+package execinfra
+
+import (
+	"context"
+	"time"
+
+	"github.com/cockroachdb/cockroach/pkg/base"
+	"github.com/cockroachdb/cockroach/pkg/roachpb"
+	"github.com/cockroachdb/cockroach/pkg/rpc"
+	"github.com/cockroachdb/cockroach/pkg/util/retry"
+	"github.com/cockroachdb/cockroach/pkg/util/timeutil"
+	"google.golang.org/grpc"
+)
+
+// Dialer is used for dialing based on node IDs. It extracts out the single
+// method that outboxes need from nodedialer.Dialer so that we can mock it
+// in tests outside of this package.
+type Dialer interface {
+	DialNoBreaker(context.Context, roachpb.NodeID, rpc.ConnectionClass) (*grpc.ClientConn, error)
+}
+
+// GetConnForOutbox is a shared function between the rowexec and colexec
+// outboxes. It attempts to dial the destination ignoring the breaker, up to the
+// given timeout and returns the connection or an error.
+// This connection attempt is retried since failure results in a query error. In
+// the past, we have seen cases where a gateway node, n1, would send a flow
+// request to n2, but n2 would be unable to connect back to n1 due to this
+// connection attempt failing.
+// Retrying here alleviates these flakes and causes no impact to the end
+// user, since the receiver at the other end will hang for
+// SettingFlowStreamTimeout waiting for a successful connection attempt.
+func GetConnForOutbox(
+	ctx context.Context, dialer Dialer, nodeID roachpb.NodeID, timeout time.Duration,
+) (conn *grpc.ClientConn, err error) {
+	firstConnectionAttempt := timeutil.Now()
+	for r := retry.StartWithCtx(ctx, base.DefaultRetryOptions()); r.Next(); {
+		conn, err = dialer.DialNoBreaker(ctx, nodeID, rpc.DefaultClass)
+		if err == nil || timeutil.Since(firstConnectionAttempt) > timeout {
+			break
+		}
+	}
+	return
+}
diff --git a/pkg/sql/execinfrapb/testutils.go b/pkg/sql/execinfrapb/testutils.go
index ec2504119bc1..eda740d7cb4a 100644
--- a/pkg/sql/execinfrapb/testutils.go
+++ b/pkg/sql/execinfrapb/testutils.go
@@ -134,8 +134,8 @@ type MockDialer struct {
 	}
 }
 
-// Dial establishes a grpc connection once.
-func (d *MockDialer) Dial(
+// DialNoBreaker establishes a grpc connection once.
+func (d *MockDialer) DialNoBreaker(
 	context.Context, roachpb.NodeID, rpc.ConnectionClass,
 ) (*grpc.ClientConn, error) {
 	d.mu.Lock()
diff --git a/pkg/sql/flowinfra/outbox.go b/pkg/sql/flowinfra/outbox.go
index b92af740271b..1525082dd8da 100644
--- a/pkg/sql/flowinfra/outbox.go
+++ b/pkg/sql/flowinfra/outbox.go
@@ -18,7 +18,6 @@ import (
 	"time"
 
 	"github.com/cockroachdb/cockroach/pkg/roachpb"
-	"github.com/cockroachdb/cockroach/pkg/rpc"
 	"github.com/cockroachdb/cockroach/pkg/sql/execinfra"
 	"github.com/cockroachdb/cockroach/pkg/sql/execinfrapb"
 	"github.com/cockroachdb/cockroach/pkg/sql/sqlbase"
@@ -29,7 +28,6 @@ import (
 	"github.com/cockroachdb/cockroach/pkg/util/timeutil"
 	"github.com/cockroachdb/cockroach/pkg/util/tracing"
 	opentracing "github.com/opentracing/opentracing-go"
-	"google.golang.org/grpc"
 )
 
 const outboxBufRows = 16
@@ -221,9 +219,9 @@ func (m *Outbox) mainLoop(ctx context.Context) error {
 	}()
 
 	if m.stream == nil {
-		var conn *grpc.ClientConn
-		var err error
-		conn, err = m.flowCtx.Cfg.NodeDialer.DialNoBreaker(ctx, m.nodeID, rpc.DefaultClass)
+		conn, err := execinfra.GetConnForOutbox(
+			ctx, m.flowCtx.Cfg.NodeDialer, m.nodeID, SettingFlowStreamTimeout.Get(&m.flowCtx.Cfg.Settings.SV),
+		)
 		if err != nil {
 			// Log any Dial errors. This does not have a verbosity check due to being
 			// a critical part of query execution: if this step doesn't work, the