diff --git a/apps/cli/src/service-container/service-container.ts b/apps/cli/src/service-container/service-container.ts
index 21e8f9f208..ce944db78f 100644
--- a/apps/cli/src/service-container/service-container.ts
+++ b/apps/cli/src/service-container/service-container.ts
@@ -17,6 +17,7 @@ import {
   PinService,
   PinServiceAbstraction,
   UserDecryptionOptionsService,
+  Executor,
 } from "@bitwarden/auth/common";
 import { EventCollectionService as EventCollectionServiceAbstraction } from "@bitwarden/common/abstractions/event/event-collection.service";
 import { EventUploadService as EventUploadServiceAbstraction } from "@bitwarden/common/abstractions/event/event-upload.service";
@@ -614,6 +615,11 @@ export class ServiceContainer {
       this.configService,
     );
 
+    // Execute any authn session timeout logic without any wrapping logic.
+    // An executor is required to ensure the logic is executed in an Angular context when it
+    // it is available.
+    const authnSessionTimeoutExecutor: Executor = (fn) => fn();
+
     this.loginStrategyService = new LoginStrategyService(
       this.accountService,
       this.masterPasswordService,
@@ -640,6 +646,7 @@ export class ServiceContainer {
       this.vaultTimeoutSettingsService,
       this.kdfConfigService,
       this.taskSchedulerService,
+      authnSessionTimeoutExecutor,
     );
 
     // FIXME: CLI does not support autofill
diff --git a/libs/angular/src/services/injection-tokens.ts b/libs/angular/src/services/injection-tokens.ts
index 86c5642a0c..69a1ed3f61 100644
--- a/libs/angular/src/services/injection-tokens.ts
+++ b/libs/angular/src/services/injection-tokens.ts
@@ -1,7 +1,7 @@
 import { InjectionToken } from "@angular/core";
 import { Observable, Subject } from "rxjs";
 
-import { LogoutReason } from "@bitwarden/auth/common";
+import { Executor, LogoutReason } from "@bitwarden/auth/common";
 import { ClientType } from "@bitwarden/common/enums";
 import { RegionConfig } from "@bitwarden/common/platform/abstractions/environment.service";
 import {
@@ -68,3 +68,7 @@ export const REFRESH_ACCESS_TOKEN_ERROR_CALLBACK = new SafeInjectionToken<() =>
 export const ENV_ADDITIONAL_REGIONS = new SafeInjectionToken<RegionConfig[]>(
   "ENV_ADDITIONAL_REGIONS",
 );
+
+export const AUTHN_SESSION_TIMEOUT_EXECUTOR = new SafeInjectionToken<Executor>(
+  "AuthnSessionTimeoutExecutor",
+);
diff --git a/libs/angular/src/services/jslib-services.module.ts b/libs/angular/src/services/jslib-services.module.ts
index a43f1fa07a..8637e26a2b 100644
--- a/libs/angular/src/services/jslib-services.module.ts
+++ b/libs/angular/src/services/jslib-services.module.ts
@@ -1,4 +1,4 @@
-import { ErrorHandler, LOCALE_ID, NgModule } from "@angular/core";
+import { ErrorHandler, LOCALE_ID, NgModule, NgZone } from "@angular/core";
 import { Subject } from "rxjs";
 
 import {
@@ -319,6 +319,7 @@ import {
   CLIENT_TYPE,
   REFRESH_ACCESS_TOKEN_ERROR_CALLBACK,
   ENV_ADDITIONAL_REGIONS,
+  AUTHN_SESSION_TIMEOUT_EXECUTOR,
 } from "./injection-tokens";
 import { ModalService } from "./modal.service";
 
@@ -411,6 +412,11 @@ const safeProviders: SafeProvider[] = [
       TokenServiceAbstraction,
     ],
   }),
+  safeProvider({
+    provide: AUTHN_SESSION_TIMEOUT_EXECUTOR,
+    useFactory: (ngZone: NgZone) => (fn: () => void) => ngZone.run(fn),
+    deps: [NgZone],
+  }),
   safeProvider({
     provide: LoginStrategyServiceAbstraction,
     useClass: LoginStrategyService,
@@ -440,6 +446,7 @@ const safeProviders: SafeProvider[] = [
       VaultTimeoutSettingsServiceAbstraction,
       KdfConfigService,
       TaskSchedulerService,
+      AUTHN_SESSION_TIMEOUT_EXECUTOR,
     ],
   }),
   safeProvider({
diff --git a/libs/auth/src/common/services/login-strategies/login-strategy.service.ts b/libs/auth/src/common/services/login-strategies/login-strategy.service.ts
index 99e3c057e1..1d5001f1f0 100644
--- a/libs/auth/src/common/services/login-strategies/login-strategy.service.ts
+++ b/libs/auth/src/common/services/login-strategies/login-strategy.service.ts
@@ -71,6 +71,8 @@ import {
 
 const sessionTimeoutLength = 5 * 60 * 1000; // 5 minutes
 
+export type Executor = (fn: () => void) => void;
+
 export class LoginStrategyService implements LoginStrategyServiceAbstraction {
   private sessionTimeoutSubscription: Subscription;
   private currentAuthnTypeState: GlobalState<AuthenticationType | null>;
@@ -118,6 +120,7 @@ export class LoginStrategyService implements LoginStrategyServiceAbstraction {
     protected vaultTimeoutSettingsService: VaultTimeoutSettingsService,
     protected kdfConfigService: KdfConfigService,
     protected taskSchedulerService: TaskSchedulerService,
+    private authnSessionTimeoutExecutor: Executor = (fn) => fn(), // Default to no-op
   ) {
     this.currentAuthnTypeState = this.stateProvider.get(CURRENT_LOGIN_STRATEGY_KEY);
     this.loginStrategyCacheState = this.stateProvider.get(CACHE_KEY);
@@ -128,12 +131,14 @@ export class LoginStrategyService implements LoginStrategyServiceAbstraction {
     this.taskSchedulerService.registerTaskHandler(
       ScheduledTaskNames.loginStrategySessionTimeout,
       async () => {
-        this.twoFactorTimeoutSubject.next(true);
-        try {
-          await this.clearCache();
-        } catch (e) {
-          this.logService.error("Failed to clear cache during session timeout", e);
-        }
+        this.authnSessionTimeoutExecutor(async () => {
+          this.twoFactorTimeoutSubject.next(true);
+          try {
+            await this.clearCache();
+          } catch (e) {
+            this.logService.error("Failed to clear cache during session timeout", e);
+          }
+        });
       },
     );