diff --git a/pkg/container/docker/client.go b/pkg/container/docker/client.go
index a0909fcfc7..e05c5155ea 100644
--- a/pkg/container/docker/client.go
+++ b/pkg/container/docker/client.go
@@ -1638,9 +1638,11 @@ func mergeEnvVars(base, extra map[string]string) map[string]string {
 // the workload and returns the host-side port it is bound on.
 func (c *Client) setupIngressContainer(ctx context.Context, containerName string, upstreamPort int, attachStdio bool,
 	externalEndpointsConfig map[string]*network.EndpointSettings, networkPermissions *permissions.NetworkPermissions) (int, error) {
-	squidPort, err := networking.FindOrUsePort(upstreamPort + 1)
+	// A random port avoids every same-image workload racing to bind the same
+	// preferred port when starting concurrently (see #6063).
+	squidPort, err := networking.FindOrUsePort(0)
 	if err != nil {
-		return 0, fmt.Errorf("failed to find or use port %d: %w", squidPort, err)
+		return 0, fmt.Errorf("failed to find an available port: %w", err)
 	}
 	squidExposedPorts := map[string]struct{}{
 		fmt.Sprintf("%d/tcp", squidPort): {},
diff --git a/pkg/container/docker/envoy.go b/pkg/container/docker/envoy.go
index 60b0be40d9..38decd6176 100644
--- a/pkg/container/docker/envoy.go
+++ b/pkg/container/docker/envoy.go
@@ -886,7 +886,9 @@ func (e *envoyProxy) SetupIngress(ctx context.Context, spec proxySpec, _ egressR
 
 	var ingressPort int
 	if spec.TransportType != "stdio" && spec.UpstreamPort > 0 {
-		port, err := networking.FindOrUsePort(spec.UpstreamPort + 1)
+		// A random port avoids every same-image workload racing to bind the
+		// same preferred port when starting concurrently (see #6063).
+		port, err := networking.FindOrUsePort(0)
 		if err != nil {
 			return 0, fmt.Errorf("failed to find ingress port: %w", err)
 		}
diff --git a/pkg/container/docker/envoy_test.go b/pkg/container/docker/envoy_test.go
index e5bfafdbd3..a45c8b0bef 100644
--- a/pkg/container/docker/envoy_test.go
+++ b/pkg/container/docker/envoy_test.go
@@ -6,10 +6,12 @@ package docker
 import (
 	"context"
 	"encoding/json"
+	"fmt"
 	"os"
 	"os/exec"
 	"regexp"
 	"strings"
+	"sync"
 	"testing"
 	"time"
 
@@ -821,6 +823,70 @@ func TestEnvoyProxy_SetupOrchestration(t *testing.T) {
 	}
 }
 
+// TestEnvoyProxy_SetupIngress_ConcurrentSameUpstreamPort guards against a
+// deterministic ingress port collision: two workloads built from the same
+// image share the same fixed UpstreamPort, so deriving the ingress port from
+// UpstreamPort+1 made every concurrently-starting instance request the
+// identical host port. The fix picks a random port instead, so concurrent
+// SetupIngress calls sharing UpstreamPort must land on different ports.
+func TestEnvoyProxy_SetupIngress_ConcurrentSameUpstreamPort(t *testing.T) {
+	t.Parallel()
+
+	const upstreamPort = 8080
+	const workloadCount = 4
+
+	ports := make([]int, workloadCount)
+	errs := make([]error, workloadCount)
+
+	var wg sync.WaitGroup
+	for i := range workloadCount {
+		wg.Add(1)
+		go func(idx int) {
+			defer wg.Done()
+			api := &fakeDockerAPI{
+				createFunc: func(_ context.Context, _ *container.Config, _ *container.HostConfig,
+					_ *network.NetworkingConfig, _ *v1.Platform, _ string) (container.CreateResponse, error) {
+					return container.CreateResponse{ID: "cid-envoy"}, nil
+				},
+				startFunc: func(_ context.Context, _ string, _ mobyclient.ContainerStartOptions) error { return nil },
+			}
+			e := &envoyProxy{client: &Client{
+				api:          api,
+				imageManager: &fakeImageManager{availableImages: map[string]struct{}{defaultEnvoyImage: {}}},
+			}}
+			spec := proxySpec{
+				WorkloadName:  fmt.Sprintf("app-%d", idx),
+				TransportType: "streamable-http",
+				UpstreamPort:  upstreamPort,
+				GatewayIP:     dockerDefaultBridgeGatewayIP,
+				Endpoints:     map[string]*network.EndpointSettings{},
+			}
+			port, err := e.SetupIngress(t.Context(), spec, egressResult{})
+			ports[idx] = port
+			errs[idx] = err
+		}(i)
+	}
+
+	done := make(chan struct{})
+	go func() {
+		wg.Wait()
+		close(done)
+	}()
+	select {
+	case <-done:
+	case <-time.After(10 * time.Second):
+		t.Fatal("timeout waiting for concurrent SetupIngress calls")
+	}
+
+	seen := make(map[int]bool, workloadCount)
+	for i, port := range ports {
+		require.NoError(t, errs[i])
+		assert.NotEqual(t, upstreamPort+1, port, "ingress port must not be derived from UpstreamPort+1")
+		assert.False(t, seen[port], "port %d was reserved by more than one concurrent workload", port)
+		seen[port] = true
+	}
+}
+
 // TestListenerTimeoutsDisabledForStreaming guards against Envoy's 15s default
 // RouteAction.timeout (a hard total-response cap) and 5m stream_idle_timeout
 // truncating long-lived MCP streams (SSE / streamable-http). Both the ingress