diff --git a/changelog/fragments/1712305270-fix-upgrade-cmd-fail-when-disconnected.yaml b/changelog/fragments/1712305270-fix-upgrade-cmd-fail-when-disconnected.yaml
new file mode 100644
index 00000000000..6158a0c6f92
--- /dev/null
+++ b/changelog/fragments/1712305270-fix-upgrade-cmd-fail-when-disconnected.yaml
@@ -0,0 +1,5 @@
+kind: bug-fix
+summary: Fix failing upgrade command when gRPC server interrupts connection
+component: "elastic-agent"
+pr: https://github.com/elastic/elastic-agent/pull/4519
+issue: https://github.com/elastic/elastic-agent/issues/3890
diff --git a/internal/pkg/agent/cmd/upgrade.go b/internal/pkg/agent/cmd/upgrade.go
index 6c33fa43498..5b02fc9bfb9 100644
--- a/internal/pkg/agent/cmd/upgrade.go
+++ b/internal/pkg/agent/cmd/upgrade.go
@@ -8,8 +8,11 @@ import (
 	"context"
 	"fmt"
 	"os"
+	"strings"
 
 	"github.com/spf13/cobra"
+	"google.golang.org/grpc/codes"
+	"google.golang.org/grpc/status"
 
 	"github.com/elastic/elastic-agent/pkg/control"
 	"github.com/elastic/elastic-agent/pkg/control/v2/client"
@@ -55,10 +58,14 @@ func newUpgradeCommandWithArgs(_ []string, streams *cli.IOStreams) *cobra.Comman
 }
 
 func upgradeCmd(streams *cli.IOStreams, cmd *cobra.Command, args []string) error {
+	c := client.New()
+	return upgradeCmdWithClient(streams, cmd, args, c)
+}
+
+func upgradeCmdWithClient(streams *cli.IOStreams, cmd *cobra.Command, args []string, c client.Client) error {
 	version := args[0]
 	sourceURI, _ := cmd.Flags().GetString(flagSourceURI)
 
-	c := client.New()
 	err := c.Connect(context.Background())
 	if err != nil {
 		return errors.New(err, "Failed communicating to running daemon", errors.TypeNetwork, errors.M("socket", control.Address()))
@@ -106,7 +113,14 @@ func upgradeCmd(streams *cli.IOStreams, cmd *cobra.Command, args []string) error
 	skipDefaultPgp, _ := cmd.Flags().GetBool(flagSkipDefaultPgp)
 	version, err = c.Upgrade(context.Background(), version, sourceURI, skipVerification, skipDefaultPgp, pgpChecks...)
 	if err != nil {
-		return errors.New(err, "Failed trigger upgrade of daemon")
+		s, ok := status.FromError(err)
+		// Sometimes the gRPC server shuts down before replying to the command which is expected
+		// we can determine this state by the EOF error coming from the server.
+		// If the server is just unavailable/not running, we should not succeed.
+		isConnectionInterrupted := ok && s.Code() == codes.Unavailable && strings.Contains(s.Message(), "EOF")
+		if !isConnectionInterrupted {
+			return errors.New(err, "Failed trigger upgrade of daemon")
+		}
 	}
 	fmt.Fprintf(streams.Out, "Upgrade triggered to version %s, Elastic Agent is currently restarting\n", version)
 	return nil
diff --git a/internal/pkg/agent/cmd/upgrade_test.go b/internal/pkg/agent/cmd/upgrade_test.go
new file mode 100644
index 00000000000..efdc6864802
--- /dev/null
+++ b/internal/pkg/agent/cmd/upgrade_test.go
@@ -0,0 +1,90 @@
+// Copyright Elasticsearch B.V. and/or licensed to Elasticsearch B.V. under one
+// or more contributor license agreements. Licensed under the Elastic License;
+// you may not use this file except in compliance with the Elastic License.
+
+package cmd
+
+import (
+	"context"
+	"net"
+	"sync/atomic"
+	"testing"
+	"time"
+
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+	"google.golang.org/grpc"
+
+	"github.com/elastic/elastic-agent/internal/pkg/cli"
+	"github.com/elastic/elastic-agent/pkg/control/v2/client"
+	"github.com/elastic/elastic-agent/pkg/control/v2/cproto"
+)
+
+func TestUpgradeCmd(t *testing.T) {
+	t.Run("no error when connection gets interrupted", func(t *testing.T) {
+		tcpServer, err := net.Listen("tcp", "127.0.0.1:")
+		require.NoError(t, err)
+		defer tcpServer.Close()
+
+		s := grpc.NewServer()
+		defer s.Stop()
+
+		upgradeCh := make(chan struct{})
+		mock := &mockServer{upgradeStop: upgradeCh}
+		cproto.RegisterElasticAgentControlServer(s, mock)
+		go func() {
+			err := s.Serve(tcpServer)
+			assert.NoError(t, err)
+		}()
+
+		clientCh := make(chan struct{})
+		// use HTTP prefix for the dialer to use TCP, otherwise it's a unix socket/named pipe
+		c := client.New(client.WithAddress("http://" + tcpServer.Addr().String()))
+		args := []string{"--skip-verify", "8.13.0"}
+		streams := cli.NewIOStreams()
+		cmd := newUpgradeCommandWithArgs(args, streams)
+
+		// the upgrade command will hang until the server shut down
+		go func() {
+			err = upgradeCmdWithClient(streams, cmd, args, c)
+			assert.NoError(t, err)
+			// verify that we actually talked to the server
+			counter := atomic.LoadInt32(&mock.upgrades)
+			assert.Equal(t, int32(1), counter, "server should have handled one upgrade")
+			// unblock the further test execution
+			close(clientCh)
+		}()
+
+		// we will know that the client reached the server watching the `mock.upgrades` counter
+		require.Eventually(t, func() bool {
+			counter := atomic.LoadInt32(&mock.upgrades)
+			return counter > 0
+		}, 5*time.Second, 100*time.Millisecond)
+
+		// then we close the tcp server which is supposed to interrupt the connection
+		s.Stop()
+		// this stops the mock server
+		close(upgradeCh)
+		// this makes sure all client assertions are done
+		<-clientCh
+	})
+}
+
+type mockServer struct {
+	cproto.ElasticAgentControlServer
+	upgradeStop <-chan struct{}
+	upgrades    int32
+}
+
+func (s *mockServer) Upgrade(ctx context.Context, r *cproto.UpgradeRequest) (resp *cproto.UpgradeResponse, err error) {
+	atomic.AddInt32(&s.upgrades, 1)
+	<-s.upgradeStop
+	return nil, nil
+}
+
+func (s *mockServer) State(ctx context.Context, r *cproto.Empty) (resp *cproto.StateResponse, err error) {
+	return &cproto.StateResponse{
+		State: cproto.State_HEALTHY,
+		Info:  &cproto.StateAgentInfo{},
+	}, nil
+}
diff --git a/testing/upgradetest/upgrader.go b/testing/upgradetest/upgrader.go
index 184c7efd213..8c36bb7581e 100644
--- a/testing/upgradetest/upgrader.go
+++ b/testing/upgradetest/upgrader.go
@@ -12,6 +12,7 @@ import (
 	"os"
 	"path/filepath"
 	"runtime"
+	"strings"
 	"time"
 
 	"github.com/otiai10/copy"
@@ -325,7 +326,14 @@ func PerformUpgrade(
 
 	upgradeOutput, err := startFixture.Exec(ctx, upgradeCmdArgs)
 	if err != nil {
-		return fmt.Errorf("failed to start agent upgrade to version %q: %w\n%s", endVersionInfo.Binary.Version, err, upgradeOutput)
+		// Sometimes the gRPC server shuts down before replying to the command which is expected
+		// we can determine this state by the EOF error coming from the server.
+		// If the server is just unavailable/not running, we should not succeed.
+		// Starting with version 8.13.2, this is handled by the upgrade command itself.
+		isConnectionInterrupted := strings.Contains(err.Error(), "Unavailable") && strings.Contains(err.Error(), "EOF")
+		if !isConnectionInterrupted {
+			return fmt.Errorf("failed to start agent upgrade to version %q: %w\n%s", endVersionInfo.Binary.Version, err, upgradeOutput)
+		}
 	}
 
 	// wait for the watcher to show up