diff --git a/src/gateway/server.auth.e2e.test.ts b/src/gateway/server.auth.e2e.test.ts
index bbfbbf29c3..7ee747abf5 100644
--- a/src/gateway/server.auth.e2e.test.ts
+++ b/src/gateway/server.auth.e2e.test.ts
@@ -925,11 +925,25 @@ describe("gateway server auth/connect", () => {
       client,
       device: buildDevice(["operator.admin"]),
     });
-    expect(res.ok).toBe(true);
+    expect(res.ok).toBe(false);
+    expect(res.error?.message ?? "").toContain("pairing required");
+
+    await approvePendingPairingIfNeeded();
+    ws2.close();
+
+    const ws3 = new WebSocket(`ws://127.0.0.1:${port}`);
+    await new Promise<void>((resolve) => ws3.once("open", resolve));
+    const approved = await connectReq(ws3, {
+      token: "secret",
+      scopes: ["operator.admin"],
+      client,
+      device: buildDevice(["operator.admin"]),
+    });
+    expect(approved.ok).toBe(true);
     paired = await getPairedDevice(identity.deviceId);
     expect(paired?.scopes).toContain("operator.admin");
 
-    ws2.close();
+    ws3.close();
     await server.close();
     restoreGatewayToken(prevToken);
   });
diff --git a/src/gateway/server/ws-connection/message-handler.ts b/src/gateway/server/ws-connection/message-handler.ts
index 7a50d1cc8a..e7496c51b1 100644
--- a/src/gateway/server/ws-connection/message-handler.ts
+++ b/src/gateway/server/ws-connection/message-handler.ts
@@ -1,6 +1,10 @@
 import type { IncomingMessage } from "node:http";
-import os from "node:os";
 import type { WebSocket } from "ws";
+import os from "node:os";
+import type { createSubsystemLogger } from "../../../logging/subsystem.js";
+import type { GatewayAuthResult, ResolvedGatewayAuth } from "../../auth.js";
+import type { GatewayRequestContext, GatewayRequestHandlers } from "../../server-methods/types.js";
+import type { GatewayWsClient } from "../ws-types.js";
 import { loadConfig } from "../../../config/config.js";
 import {
   deriveDeviceIdFromPublicKey,
@@ -20,7 +24,6 @@ import { recordRemoteNodeInfo, refreshRemoteNodeBins } from "../../../infra/skil
 import { upsertPresence } from "../../../infra/system-presence.js";
 import { loadVoiceWakeConfig } from "../../../infra/voicewake.js";
 import { rawDataToString } from "../../../infra/ws.js";
-import type { createSubsystemLogger } from "../../../logging/subsystem.js";
 import { isGatewayCliClient, isWebchatClient } from "../../../utils/message-channel.js";
 import { resolveRuntimeServiceVersion } from "../../../version.js";
 import {
@@ -28,7 +31,6 @@ import {
   AUTH_RATE_LIMIT_SCOPE_SHARED_SECRET,
   type AuthRateLimiter,
 } from "../../auth-rate-limit.js";
-import type { GatewayAuthResult, ResolvedGatewayAuth } from "../../auth.js";
 import { authorizeGatewayConnect, isLocalDirectRequest } from "../../auth.js";
 import { buildDeviceAuthPayload } from "../../device-auth.js";
 import { isLoopbackAddress, isTrustedProxyAddress, resolveGatewayClientIp } from "../../net.js";
@@ -48,7 +50,6 @@ import {
 } from "../../protocol/index.js";
 import { MAX_BUFFERED_BYTES, MAX_PAYLOAD_BYTES, TICK_INTERVAL_MS } from "../../server-constants.js";
 import { handleGatewayRequest } from "../../server-methods.js";
-import type { GatewayRequestContext, GatewayRequestHandlers } from "../../server-methods/types.js";
 import { formatError } from "../../server-utils.js";
 import { formatForLog, logWs } from "../../ws-log.js";
 import { truncateCloseReason } from "../close-reason.js";
@@ -59,7 +60,6 @@ import {
   incrementPresenceVersion,
   refreshGatewayHealthSnapshot,
 } from "../health-state.js";
-import type { GatewayWsClient } from "../ws-types.js";
 import { formatGatewayAuthFailureMessage, type AuthProvidedKind } from "./auth-messages.js";
 
 type SubsystemLogger = ReturnType<typeof createSubsystemLogger>;
@@ -616,7 +616,34 @@ export function attachGatewayWsMessageHandler(params: {
 
         const skipPairing = allowControlUiBypass && sharedAuthOk;
         if (device && devicePublicKey && !skipPairing) {
-          const requirePairing = async (reason: string, _paired?: { deviceId: string }) => {
+          const formatAuditList = (items: string[] | undefined): string => {
+            if (!items || items.length === 0) {
+              return "<none>";
+            }
+            const out = new Set<string>();
+            for (const item of items) {
+              const trimmed = item.trim();
+              if (trimmed) {
+                out.add(trimmed);
+              }
+            }
+            if (out.size === 0) {
+              return "<none>";
+            }
+            return [...out].toSorted().join(",");
+          };
+          const logUpgradeAudit = (
+            reason: "role-upgrade" | "scope-upgrade",
+            currentRoles: string[] | undefined,
+            currentScopes: string[] | undefined,
+          ) => {
+            logGateway.warn(
+              `security audit: device access upgrade requested reason=${reason} device=${device.id} ip=${reportedClientIp ?? "unknown-ip"} auth=${authMethod} roleFrom=${formatAuditList(currentRoles)} roleTo=${role} scopesFrom=${formatAuditList(currentScopes)} scopesTo=${formatAuditList(scopes)} client=${connectParams.client.id} conn=${connId}`,
+            );
+          };
+          const requirePairing = async (
+            reason: "not-paired" | "role-upgrade" | "scope-upgrade",
+          ) => {
             const pairing = await requestDevicePairing({
               deviceId: device.id,
               publicKey: devicePublicKey,
@@ -627,7 +654,7 @@ export function attachGatewayWsMessageHandler(params: {
               role,
               scopes,
               remoteIp: reportedClientIp,
-              silent: isLocalClient,
+              silent: isLocalClient && reason === "not-paired",
             });
             const context = buildRequestContext();
             if (pairing.request.silent === true) {
@@ -679,16 +706,21 @@ export function attachGatewayWsMessageHandler(params: {
               return;
             }
           } else {
-            const allowedRoles = new Set(
-              Array.isArray(paired.roles) ? paired.roles : paired.role ? [paired.role] : [],
-            );
+            const pairedRoles = Array.isArray(paired.roles)
+              ? paired.roles
+              : paired.role
+                ? [paired.role]
+                : [];
+            const allowedRoles = new Set(pairedRoles);
             if (allowedRoles.size === 0) {
-              const ok = await requirePairing("role-upgrade", paired);
+              logUpgradeAudit("role-upgrade", pairedRoles, paired.scopes);
+              const ok = await requirePairing("role-upgrade");
               if (!ok) {
                 return;
               }
             } else if (!allowedRoles.has(role)) {
-              const ok = await requirePairing("role-upgrade", paired);
+              logUpgradeAudit("role-upgrade", pairedRoles, paired.scopes);
+              const ok = await requirePairing("role-upgrade");
               if (!ok) {
                 return;
               }
@@ -697,7 +729,8 @@ export function attachGatewayWsMessageHandler(params: {
             const pairedScopes = Array.isArray(paired.scopes) ? paired.scopes : [];
             if (scopes.length > 0) {
               if (pairedScopes.length === 0) {
-                const ok = await requirePairing("scope-upgrade", paired);
+                logUpgradeAudit("scope-upgrade", pairedRoles, pairedScopes);
+                const ok = await requirePairing("scope-upgrade");
                 if (!ok) {
                   return;
                 }
@@ -705,7 +738,8 @@ export function attachGatewayWsMessageHandler(params: {
                 const allowedScopes = new Set(pairedScopes);
                 const missingScope = scopes.find((scope) => !allowedScopes.has(scope));
                 if (missingScope) {
-                  const ok = await requirePairing("scope-upgrade", paired);
+                  logUpgradeAudit("scope-upgrade", pairedRoles, pairedScopes);
+                  const ok = await requirePairing("scope-upgrade");
                   if (!ok) {
                     return;
                   }