diff --git a/cmd/tailscale/cli/cli.go b/cmd/tailscale/cli/cli.go
index 4e777c2df..9c5a3ab6b 100644
--- a/cmd/tailscale/cli/cli.go
+++ b/cmd/tailscale/cli/cli.go
@@ -8,8 +8,10 @@ package cli
 
 import (
 	"context"
+	"errors"
 	"flag"
 	"fmt"
+	"io"
 	"log"
 	"net"
 	"os"
@@ -169,21 +171,22 @@ func connect(ctx context.Context) (net.Conn, *ipn.BackendClient, context.Context
 }
 
 // pump receives backend messages on conn and pushes them into bc.
-func pump(ctx context.Context, bc *ipn.BackendClient, conn net.Conn) {
+func pump(ctx context.Context, bc *ipn.BackendClient, conn net.Conn) error {
 	defer conn.Close()
 	for ctx.Err() == nil {
 		msg, err := ipn.ReadMsg(conn)
 		if err != nil {
 			if ctx.Err() != nil {
-				return
+				return ctx.Err()
 			}
-			if !gotSignal.Get() {
-				log.Printf("ReadMsg: %v\n", err)
+			if errors.Is(err, io.EOF) || errors.Is(err, net.ErrClosed) {
+				return fmt.Errorf("%w (tailscaled stopped running?)", err)
 			}
-			break
+			return err
 		}
 		bc.GotNotifyMsg(msg)
 	}
+	return ctx.Err()
 }
 
 func strSliceContains(ss []string, s string) bool {
diff --git a/cmd/tailscale/cli/ping.go b/cmd/tailscale/cli/ping.go
index be9261038..3f08cc138 100644
--- a/cmd/tailscale/cli/ping.go
+++ b/cmd/tailscale/cli/ping.go
@@ -80,7 +80,8 @@ func runPing(ctx context.Context, args []string) error {
 			prc <- pr
 		}
 	})
-	go pump(ctx, bc, c)
+	pumpErr := make(chan error, 1)
+	go func() { pumpErr <- pump(ctx, bc, c) }()
 
 	hostOrIP := args[0]
 	ip, err := tailscaleIPFromArg(ctx, hostOrIP)
@@ -101,6 +102,8 @@ func runPing(ctx context.Context, args []string) error {
 		select {
 		case <-timer.C:
 			fmt.Printf("timeout waiting for ping reply\n")
+		case err := <-pumpErr:
+			return err
 		case pr := <-prc:
 			timer.Stop()
 			if pr.Err != "" {
diff --git a/cmd/tailscale/cli/up.go b/cmd/tailscale/cli/up.go
index d5d7fa6f4..911656ad5 100644
--- a/cmd/tailscale/cli/up.go
+++ b/cmd/tailscale/cli/up.go
@@ -344,7 +344,8 @@ func runUp(ctx context.Context, args []string) error {
 
 	startingOrRunning := make(chan bool, 1) // gets value once starting or running
 	gotEngineUpdate := make(chan bool, 1)   // gets value upon an engine update
-	go pump(pumpCtx, bc, c)
+	pumpErr := make(chan error, 1)
+	go func() { pumpErr <- pump(pumpCtx, bc, c) }()
 
 	printed := !simpleUp
 	var loginOnce sync.Once
@@ -404,6 +405,8 @@ func runUp(ctx context.Context, args []string) error {
 	case <-gotEngineUpdate:
 	case <-pumpCtx.Done():
 		return pumpCtx.Err()
+	case err := <-pumpErr:
+		return err
 	}
 
 	// Special case: bare "tailscale up" means to just start
@@ -456,6 +459,8 @@ func runUp(ctx context.Context, args []string) error {
 		default:
 		}
 		return pumpCtx.Err()
+	case err := <-pumpErr:
+		return err
 	}
 }