diff --git a/internal/dockeragent/agent.go b/internal/dockeragent/agent.go
index 45c23ca61..0a0beb72e 100644
--- a/internal/dockeragent/agent.go
+++ b/internal/dockeragent/agent.go
@@ -939,9 +939,16 @@ func (a *Agent) handleCheckUpdatesCommand(ctx context.Context, target TargetConf
 		a.registryChecker.ForceCheck()
 	}
 
-	// Send intermediate completion ack
+	// Send intermediate completion ack. Don't propagate the error — the
+	// report was already delivered successfully. Propagating causes the
+	// report to be buffered and retried, which re-fetches the same command
+	// and creates a loop (issue #1504).
 	if err := a.sendCommandAck(ctx, target, command.ID, agentsdocker.CommandStatusCompleted, "Registry cache cleared; checking for updates on next report cycle"); err != nil {
-		return fmt.Errorf("send check updates acknowledgement: %w", err)
+		a.logger.Warn().
+			Err(err).
+			Str("commandID", command.ID).
+			Str("target", target.URL).
+			Msg("Failed to send check updates acknowledgement")
 	}
 
 	// Trigger an immediate collection cycle to report updates.
diff --git a/internal/dockeragent/agent_http_test.go b/internal/dockeragent/agent_http_test.go
index 6e10cd59d..aef7b3655 100644
--- a/internal/dockeragent/agent_http_test.go
+++ b/internal/dockeragent/agent_http_test.go
@@ -600,7 +600,7 @@ func TestHandleCommand(t *testing.T) {
 		}
 	})
 
-	t.Run("check updates command ack error", func(t *testing.T) {
+	t.Run("check updates command ack error does not propagate", func(t *testing.T) {
 		registryChecker := NewRegistryChecker(zerolog.Nop())
 		registryChecker.MarkChecked()
 		registryChecker.cacheDigest("cached-key", "sha256:cached")
@@ -610,13 +610,14 @@ func TestHandleCommand(t *testing.T) {
 			hostID:          "host1",
 			registryChecker: registryChecker,
 		}
+		t.Cleanup(func() { _ = agent.Close() })
 
 		err := agent.handleCheckUpdatesCommand(context.Background(), TargetConfig{URL: "http://example.com/\x7f", Token: "token"}, agentsdocker.Command{
 			ID:   "cmd4",
 			Type: agentsdocker.CommandTypeCheckUpdates,
 		})
-		if err == nil || !strings.Contains(err.Error(), "send check updates acknowledgement") {
-			t.Fatalf("expected check-updates ack error, got %v", err)
+		if err != nil {
+			t.Fatalf("expected nil error on ack failure, got: %v", err)
 		}
 
 		registryChecker.mu.RLock()
diff --git a/internal/monitoring/docker_commands.go b/internal/monitoring/docker_commands.go
index 87f10fb8a..856a02fb2 100644
--- a/internal/monitoring/docker_commands.go
+++ b/internal/monitoring/docker_commands.go
@@ -400,12 +400,17 @@ func (m *Monitor) getDockerCommandPayload(hostID string) (map[string]any, *model
 		return nil, nil
 	}
 
-	// Update dispatch metadata
-	if cmd.status.Status == DockerCommandStatusQueued {
-		cmd.markDispatched()
-		m.state.SetDockerHostCommand(hostID, &cmd.status)
+	// Only return the command on the first dispatch (queued → dispatched).
+	// Re-sending an already-dispatched command causes the agent to re-execute
+	// it on every report cycle until the ack succeeds, creating an infinite
+	// loop when the ack HTTP call fails (issue #1504).
+	if cmd.status.Status != DockerCommandStatusQueued {
+		return nil, nil
 	}
 
+	cmd.markDispatched()
+	m.state.SetDockerHostCommand(hostID, &cmd.status)
+
 	statusCopy := cmd.status
 	return cmd.payload, &statusCopy
 }
diff --git a/internal/monitoring/docker_commands_test.go b/internal/monitoring/docker_commands_test.go
index 320f74cb0..355823118 100644
--- a/internal/monitoring/docker_commands_test.go
+++ b/internal/monitoring/docker_commands_test.go
@@ -891,7 +891,7 @@ func TestGetDockerCommandPayload(t *testing.T) {
 		}
 	})
 
-	t.Run("already dispatched command is not re-marked", func(t *testing.T) {
+	t.Run("already dispatched command is not re-sent", func(t *testing.T) {
 		t.Parallel()
 
 		monitor := newTestMonitorForCommands(t)
@@ -910,39 +910,24 @@ func TestGetDockerCommandPayload(t *testing.T) {
 			t.Fatalf("queue stop command: %v", err)
 		}
 
-		// First fetch - marks as dispatched
+		// First fetch - marks as dispatched and returns status
 		_, status1 := monitor.getDockerCommandPayload(host.ID)
 		if status1 == nil {
 			t.Fatal("expected status from first fetch")
 		}
-		firstDispatchedAt := status1.DispatchedAt
-		firstUpdatedAt := status1.UpdatedAt
-
-		// Small delay to ensure time would change if re-marked
-		time.Sleep(time.Millisecond)
-
-		// Second fetch - should NOT re-mark
-		_, status2 := monitor.getDockerCommandPayload(host.ID)
-		if status2 == nil {
-			t.Fatal("expected status from second fetch")
+		if status1.Status != DockerCommandStatusDispatched {
+			t.Fatalf("expected dispatched status, got %q", status1.Status)
 		}
 
-		// DispatchedAt should be the same
-		if status2.DispatchedAt == nil {
-			t.Fatal("expected DispatchedAt to still be set")
+		// Second fetch - should return nil. The command was already delivered
+		// in the first dispatch response; re-sending it causes the agent to
+		// re-execute the command on every report cycle (issue #1504).
+		payload2, status2 := monitor.getDockerCommandPayload(host.ID)
+		if payload2 != nil {
+			t.Fatalf("expected nil payload from second fetch, got %v", payload2)
 		}
-		if !status2.DispatchedAt.Equal(*firstDispatchedAt) {
-			t.Fatalf("DispatchedAt changed: first=%v, second=%v", *firstDispatchedAt, *status2.DispatchedAt)
-		}
-
-		// UpdatedAt should be the same (not re-updated)
-		if !status2.UpdatedAt.Equal(firstUpdatedAt) {
-			t.Fatalf("UpdatedAt changed: first=%v, second=%v", firstUpdatedAt, status2.UpdatedAt)
-		}
-
-		// Status should still be dispatched
-		if status2.Status != DockerCommandStatusDispatched {
-			t.Fatalf("expected dispatched status, got %q", status2.Status)
+		if status2 != nil {
+			t.Fatalf("expected nil status from second fetch, got %+v", status2)
 		}
 	})