diff --git a/packages/@lwc/engine-core/src/framework/__tests__/context.spec.ts b/packages/@lwc/engine-core/src/framework/__tests__/context.spec.ts
new file mode 100644
index 0000000000..a8b098e2d9
--- /dev/null
+++ b/packages/@lwc/engine-core/src/framework/__tests__/context.spec.ts
@@ -0,0 +1,110 @@
+/*
+ * Copyright (c) 2025, salesforce.com, inc.
+ * All rights reserved.
+ * SPDX-License-Identifier: MIT
+ * For full license text, see the LICENSE file in the repo root or https://opensource.org/licenses/MIT
+ */
+import { describe, it, expect, vi, beforeAll, afterEach, afterAll } from 'vitest';
+import { setTrustedContextSet, setContextKeys } from '@lwc/shared';
+import { logWarnOnce } from '../../shared/logger';
+import { connectContext, disconnectContext } from '../modules/context';
+
+// Mock the logger to inspect console output during tests
+vi.mock('../../shared/logger', () => ({
+    logWarnOnce: vi.fn(),
+}));
+
+// Create mock component with a regular, non-contextful property
+const mockComponent = {};
+Object.setPrototypeOf(mockComponent, {
+    regularProp: 'not contextful',
+});
+
+// Create mock renderer
+const mockRenderer = {
+    registerContextProvider: vi.fn(),
+};
+
+// Create mock VM
+const mockVM = {
+    component: mockComponent,
+    elm: null,
+    renderer: mockRenderer,
+} as any;
+
+if (!(globalThis as any).lwcRuntimeFlags) {
+    Object.defineProperty(globalThis, 'lwcRuntimeFlags', { value: {} });
+}
+
+/**
+ * Need to be able to set and reset the flags at will (lwc/features doesn't provide this)
+ */
+const setFeatureFlag = (name: string, value: boolean) => {
+    (globalThis as any).lwcRuntimeFlags[name] = value;
+};
+
+/**
+ * These tests test that properties are correctly validated within the connectContext and disconnectContext
+ * functions regardless of whether trusted context has been defined or not.
+ * Integration tests have been used for extensive coverage of the LWC context feature, but this particular
+ * scenario is best isolated and unit tested as it involves manipulation of the trusted context API.
+ * See bug fix: #5492
+ */
+describe('context functions', () => {
+    beforeAll(() => {
+        const connectContext = Symbol('connectContext');
+        const disconnectContext = Symbol('disconnectContext');
+        setContextKeys({ connectContext, disconnectContext });
+    });
+
+    afterEach(() => {
+        vi.clearAllMocks();
+    });
+
+    afterAll(() => {
+        setFeatureFlag('ENABLE_LEGACY_SIGNAL_CONTEXT_VALIDATION', false);
+    });
+
+    describe('without setting trusted context', () => {
+        it('should log a warning when trustedContext is not defined and connectContext is called with legacy signal context validation', () => {
+            setFeatureFlag('ENABLE_LEGACY_SIGNAL_CONTEXT_VALIDATION', true);
+            connectContext(mockVM);
+            expect(logWarnOnce).toHaveBeenCalledWith(
+                'Attempted to connect to trusted context but received the following error: component[contextfulKeys[i]][connectContext2] is not a function'
+            );
+        });
+
+        it('should not log a warning when trustedContext is not defined and connectContext is called with non-legacy context validation', () => {
+            setFeatureFlag('ENABLE_LEGACY_SIGNAL_CONTEXT_VALIDATION', false);
+            connectContext(mockVM);
+            expect(logWarnOnce).not.toHaveBeenCalled();
+        });
+
+        it('should log a warning when trustedContext is not defined and disconnectContext is called with legacy signal context validation', () => {
+            setFeatureFlag('ENABLE_LEGACY_SIGNAL_CONTEXT_VALIDATION', true);
+            disconnectContext(mockVM);
+            expect(logWarnOnce).toHaveBeenCalledWith(
+                'Attempted to disconnect from trusted context but received the following error: component[contextfulKeys[i]][disconnectContext2] is not a function'
+            );
+        });
+
+        it('should not log a warning when trustedContext is not defined and disconnectContext is called with non-legacy context validation', () => {
+            setFeatureFlag('ENABLE_LEGACY_SIGNAL_CONTEXT_VALIDATION', false);
+            disconnectContext(mockVM);
+            expect(logWarnOnce).not.toHaveBeenCalled();
+        });
+    });
+
+    describe('with trusted context set', () => {
+        it('should not log warnings when trustedContext is defined', () => {
+            setTrustedContextSet(new WeakSet());
+            setFeatureFlag('ENABLE_LEGACY_SIGNAL_CONTEXT_VALIDATION', true);
+            connectContext(mockVM);
+            disconnectContext(mockVM);
+            setFeatureFlag('ENABLE_LEGACY_SIGNAL_CONTEXT_VALIDATION', false);
+            connectContext(mockVM);
+            disconnectContext(mockVM);
+            expect(logWarnOnce).not.toHaveBeenCalled();
+        });
+    });
+});
diff --git a/packages/@lwc/engine-core/src/framework/__tests__/mutation-tracker.spec.ts b/packages/@lwc/engine-core/src/framework/__tests__/mutation-tracker.spec.ts
new file mode 100644
index 0000000000..9fe774772c
--- /dev/null
+++ b/packages/@lwc/engine-core/src/framework/__tests__/mutation-tracker.spec.ts
@@ -0,0 +1,86 @@
+/*
+ * Copyright (c) 2019, salesforce.com, inc.
+ * All rights reserved.
+ * SPDX-License-Identifier: MIT
+ * For full license text, see the LICENSE file in the repo root or https://opensource.org/licenses/MIT
+ */
+import { describe, it, expect, vi, afterEach, beforeEach, afterAll, beforeAll } from 'vitest';
+import { setTrustedSignalSet } from '@lwc/shared';
+import { componentValueObserved } from '../../framework/mutation-tracker';
+
+// Create a mock VM object with required properties
+const mockVM = {
+    component: {},
+    tro: {
+        isObserving: () => true,
+    },
+} as any;
+
+if (!(globalThis as any).lwcRuntimeFlags) {
+    Object.defineProperty(globalThis, 'lwcRuntimeFlags', { value: {} });
+}
+
+/**
+ * Need to be able to set and reset the flags at will (lwc/features doesn't provide this)
+ */
+const setFeatureFlag = (name: string, value: boolean) => {
+    (globalThis as any).lwcRuntimeFlags[name] = value;
+};
+
+/**
+ * These tests check that properties are correctly validated within the mutation-tracker
+ * regardless of whether trusted context has been defined by a state manager or not.
+ * Integration tests have been used for extensive coverage of the LWC signals feature, but this particular
+ * scenario is best isolated and unit tested as it involves manipulation of the trusted context API.
+ * See bug fix: #5492
+ */
+describe('mutation-tracker', () => {
+    describe('trustedSignal set not defined', () => {
+        it('should not throw when componentValueObserved is called using the new signals validation', () => {
+            setFeatureFlag('ENABLE_LEGACY_SIGNAL_CONTEXT_VALIDATION', false);
+            expect(() => {
+                componentValueObserved(mockVM, 'testKey', {});
+            }).not.toThrow();
+        });
+
+        it('should throw when componentValueObserved is called using legacy signals validation', () => {
+            setFeatureFlag('ENABLE_LEGACY_SIGNAL_CONTEXT_VALIDATION', true);
+            expect(() => {
+                componentValueObserved(mockVM, 'testKey', {});
+            }).toThrow();
+        });
+    });
+
+    describe('trustedSignal set defined', () => {
+        it('should not throw when componentValueObserved is called, regardless of validation type', () => {
+            setTrustedSignalSet(new WeakSet());
+            setFeatureFlag('ENABLE_LEGACY_SIGNAL_CONTEXT_VALIDATION', false);
+            expect(() => {
+                componentValueObserved(mockVM, 'testKey', {});
+            }).not.toThrow();
+
+            setFeatureFlag('ENABLE_LEGACY_SIGNAL_CONTEXT_VALIDATION', true);
+            expect(() => {
+                componentValueObserved(mockVM, 'testKey', {});
+            }).not.toThrow();
+        });
+    });
+
+    beforeAll(() => {
+        setFeatureFlag('ENABLE_EXPERIMENTAL_SIGNALS', true);
+        setFeatureFlag('ENABLE_LEGACY_SIGNAL_CONTEXT_VALIDATION', true);
+    });
+
+    afterAll(() => {
+        setFeatureFlag('ENABLE_EXPERIMENTAL_SIGNALS', false);
+        setFeatureFlag('ENABLE_LEGACY_SIGNAL_CONTEXT_VALIDATION', false);
+    });
+
+    beforeEach(() => {
+        vi.stubEnv('IS_BROWSER', 'true'); // Signals is a browser-only feature
+    });
+
+    afterEach(() => {
+        vi.unstubAllEnvs(); // Reset environment variables after each test
+    });
+});
diff --git a/packages/@lwc/engine-core/src/framework/modules/context.ts b/packages/@lwc/engine-core/src/framework/modules/context.ts
index 4e406f2125..8bbd0b6190 100644
--- a/packages/@lwc/engine-core/src/framework/modules/context.ts
+++ b/packages/@lwc/engine-core/src/framework/modules/context.ts
@@ -12,6 +12,7 @@ import {
     ArrayFilter,
     ContextEventName,
     isTrustedContext,
+    legacyIsTrustedContext,
     type ContextProvidedCallback,
     type ContextBinding as IContextBinding,
 } from '@lwc/shared';
@@ -92,7 +93,17 @@ export function connectContext(vm: VM) {
 
     const enumerableKeys = keys(getPrototypeOf(component));
     const contextfulKeys = ArrayFilter.call(enumerableKeys, (enumerableKey) =>
-        isTrustedContext((component as any)[enumerableKey])
+        /**
+         * The legacy validation behavior was that this check should only
+         * be performed for runtimes that have provided a trustedContext set.
+         * However, this resulted in a bug as all object values were
+         * being considered context in environments where the trustedContext
+         * set had not been provided. The runtime flag has been added as a killswitch
+         * in case the fix needs to be reverted.
+         */
+        lwcRuntimeFlags.ENABLE_LEGACY_SIGNAL_CONTEXT_VALIDATION
+            ? legacyIsTrustedContext((component as any)[enumerableKey])
+            : isTrustedContext((component as any)[enumerableKey])
     );
 
     if (contextfulKeys.length === 0) {
@@ -128,7 +139,17 @@ export function disconnectContext(vm: VM) {
 
     const enumerableKeys = keys(getPrototypeOf(component));
     const contextfulKeys = ArrayFilter.call(enumerableKeys, (enumerableKey) =>
-        isTrustedContext((component as any)[enumerableKey])
+        /**
+         * The legacy validation behavior was that this check should only
+         * be performed for runtimes that have provided a trustedContext set.
+         * However, this resulted in a bug as all object values were
+         * being considered context in environments where the trustedContext
+         * set had not been provided. The runtime flag has been added as a killswitch
+         * in case the fix needs to be reverted.
+         */
+        lwcRuntimeFlags.ENABLE_LEGACY_SIGNAL_CONTEXT_VALIDATION
+            ? legacyIsTrustedContext((component as any)[enumerableKey])
+            : isTrustedContext((component as any)[enumerableKey])
     );
 
     if (contextfulKeys.length === 0) {
diff --git a/packages/@lwc/engine-core/src/framework/mutation-tracker.ts b/packages/@lwc/engine-core/src/framework/mutation-tracker.ts
index 3ed830fc64..d28bd0225e 100644
--- a/packages/@lwc/engine-core/src/framework/mutation-tracker.ts
+++ b/packages/@lwc/engine-core/src/framework/mutation-tracker.ts
@@ -4,7 +4,7 @@
  * SPDX-License-Identifier: MIT
  * For full license text, see the LICENSE file in the repo root or https://opensource.org/licenses/MIT
  */
-import { isNull, isObject, isTrustedSignal } from '@lwc/shared';
+import { isNull, isObject, isTrustedSignal, legacyIsTrustedSignal } from '@lwc/shared';
 import { ReactiveObserver, valueMutated, valueObserved } from '../libs/mutation-tracker';
 import { subscribeToSignal } from '../libs/signal-tracker';
 import type { Signal } from '@lwc/signals';
@@ -41,13 +41,26 @@ export function componentValueObserved(vm: VM, key: PropertyKey, target: any = {
         lwcRuntimeFlags.ENABLE_EXPERIMENTAL_SIGNALS &&
         isObject(target) &&
         !isNull(target) &&
-        isTrustedSignal(target) &&
         process.env.IS_BROWSER &&
         // Only subscribe if a template is being rendered by the engine
         tro.isObserving()
     ) {
-        // Subscribe the template reactive observer's notify method, which will mark the vm as dirty and schedule hydration.
-        subscribeToSignal(component, target as Signal<unknown>, tro.notify.bind(tro));
+        /**
+         * The legacy validation behavior was that this check should only
+         * be performed for runtimes that have provided a trustedSignals set.
+         * However, this resulted in a bug as all object values were
+         * being considered signals in environments where the trustedSignals
+         * set had not been defined. The runtime flag has been added as a killswitch
+         * in case the fix needs to be reverted.
+         */
+        if (
+            lwcRuntimeFlags.ENABLE_LEGACY_SIGNAL_CONTEXT_VALIDATION
+                ? legacyIsTrustedSignal(target)
+                : isTrustedSignal(target)
+        ) {
+            // Subscribe the template reactive observer's notify method, which will mark the vm as dirty and schedule hydration.
+            subscribeToSignal(component, target as Signal<unknown>, tro.notify.bind(tro));
+        }
     }
 }
 
diff --git a/packages/@lwc/features/src/index.ts b/packages/@lwc/features/src/index.ts
index 2c4608d7b0..3b8c54543c 100644
--- a/packages/@lwc/features/src/index.ts
+++ b/packages/@lwc/features/src/index.ts
@@ -19,6 +19,7 @@ const features: FeatureFlagMap = {
     ENABLE_LEGACY_SCOPE_TOKENS: null,
     ENABLE_FORCE_SHADOW_MIGRATE_MODE: null,
     ENABLE_EXPERIMENTAL_SIGNALS: null,
+    ENABLE_LEGACY_SIGNAL_CONTEXT_VALIDATION: null,
     DISABLE_SYNTHETIC_SHADOW: null,
     DISABLE_SCOPE_TOKEN_VALIDATION: null,
     LEGACY_LOCKER_ENABLED: null,
diff --git a/packages/@lwc/features/src/types.ts b/packages/@lwc/features/src/types.ts
index ab7984b7a8..f72698d373 100644
--- a/packages/@lwc/features/src/types.ts
+++ b/packages/@lwc/features/src/types.ts
@@ -70,6 +70,13 @@ export interface FeatureFlagMap {
      */
     ENABLE_EXPERIMENTAL_SIGNALS: FeatureFlagValue;
 
+    /**
+     * If true, legacy signal validation is used, where all component properties are considered signals or context
+     * if a trustedSignalSet and trustedContextSet have not been provided via setTrustedSignalSet and setTrustedContextSet.
+     * This is a killswitch for a bug fix: #5492
+     */
+    ENABLE_LEGACY_SIGNAL_CONTEXT_VALIDATION: FeatureFlagValue;
+
     /**
      * If true, ignore `@lwc/synthetic-shadow` even if it's loaded on the page. Instead, run all components in
      * native shadow mode.
diff --git a/packages/@lwc/shared/src/__tests__/context.spec.ts b/packages/@lwc/shared/src/__tests__/context.spec.ts
index d5fdf67093..74847d0741 100644
--- a/packages/@lwc/shared/src/__tests__/context.spec.ts
+++ b/packages/@lwc/shared/src/__tests__/context.spec.ts
@@ -12,6 +12,7 @@ describe('context', () => {
     let setTrustedContextSet: (signals: WeakSet<object>) => void;
     let addTrustedContext: (signal: object) => void;
     let isTrustedContext: (target: object) => boolean;
+    let legacyIsTrustedContext: (target: object) => boolean;
 
     beforeEach(async () => {
         vi.resetModules();
@@ -21,6 +22,7 @@ describe('context', () => {
         setTrustedContextSet = contextModule.setTrustedContextSet;
         addTrustedContext = contextModule.addTrustedContext;
         isTrustedContext = contextModule.isTrustedContext;
+        legacyIsTrustedContext = contextModule.legacyIsTrustedContext;
     });
 
     it('should set and get context keys', () => {
@@ -96,8 +98,12 @@ describe('context', () => {
             expect(isTrustedContext({})).toBe(false);
         });
 
-        it('should return true for all calls when trustedContexts is not set', () => {
-            expect(isTrustedContext({})).toBe(true);
+        it('should return false for all calls when trustedContexts is not set', () => {
+            expect(isTrustedContext({})).toBe(false);
+        });
+
+        it('legacyIsTrustedContext should return true when trustedContexts is not set', () => {
+            expect(legacyIsTrustedContext({})).toBe(true);
         });
     });
 });
diff --git a/packages/@lwc/shared/src/__tests__/signals.spec.ts b/packages/@lwc/shared/src/__tests__/signals.spec.ts
index b958052a79..81f5243d1f 100644
--- a/packages/@lwc/shared/src/__tests__/signals.spec.ts
+++ b/packages/@lwc/shared/src/__tests__/signals.spec.ts
@@ -10,6 +10,7 @@ describe('signals', () => {
     let setTrustedSignalSet: (signals: WeakSet<object>) => void;
     let addTrustedSignal: (signal: object) => void;
     let isTrustedSignal: (target: object) => boolean;
+    let legacyIsTrustedSignal: (target: object) => boolean;
 
     beforeEach(async () => {
         vi.resetModules();
@@ -17,6 +18,7 @@ describe('signals', () => {
         setTrustedSignalSet = signalsModule.setTrustedSignalSet;
         addTrustedSignal = signalsModule.addTrustedSignal;
         isTrustedSignal = signalsModule.isTrustedSignal;
+        legacyIsTrustedSignal = signalsModule.legacyIsTrustedSignal;
     });
 
     describe('setTrustedSignalSet', () => {
@@ -53,8 +55,12 @@ describe('signals', () => {
             expect(isTrustedSignal({})).toBe(false);
         });
 
-        it('should return true for all calls when trustedSignals is not set', () => {
-            expect(isTrustedSignal({})).toBe(true);
+        it('should return false for all calls when trustedSignals is not set', () => {
+            expect(isTrustedSignal({})).toBe(false);
+        });
+
+        it('legacyIsTrustedSignal should return true when trustedSignals is not set', () => {
+            expect(legacyIsTrustedSignal({})).toBe(true);
         });
     });
 });
diff --git a/packages/@lwc/shared/src/context.ts b/packages/@lwc/shared/src/context.ts
index a75ac4402c..d8f0adf168 100644
--- a/packages/@lwc/shared/src/context.ts
+++ b/packages/@lwc/shared/src/context.ts
@@ -47,11 +47,19 @@ export function setTrustedContextSet(context: WeakSet<object>) {
 }
 
 export function addTrustedContext(contextParticipant: object) {
-    // This should be a no-op when the trustedSignals set isn't set by runtime
+    // This should be a no-op when the trustedContext set isn't set by runtime
     trustedContext?.add(contextParticipant);
 }
 
-export function isTrustedContext(target: object): boolean {
+/**
+ * The legacy validation behavior was that this check should only
+ * be performed for runtimes that have provided a trustedContext set.
+ * However, this resulted in a bug as all object values were
+ * being considered context in environments where the trustedContext
+ * set had not been provided. The runtime flag has been added as a killswitch
+ * in case the fix needs to be reverted.
+ */
+export function legacyIsTrustedContext(target: object): boolean {
     if (!trustedContext) {
         // The runtime didn't set a trustedContext set
         // this check should only be performed for runtimes that care about filtering context participants to track
@@ -59,3 +67,10 @@ export function isTrustedContext(target: object): boolean {
     }
     return trustedContext.has(target);
 }
+
+export function isTrustedContext(target: object): boolean {
+    if (!trustedContext) {
+        return false;
+    }
+    return trustedContext.has(target);
+}
diff --git a/packages/@lwc/shared/src/signals.ts b/packages/@lwc/shared/src/signals.ts
index 5bfb66b27c..9a5cccd3e4 100644
--- a/packages/@lwc/shared/src/signals.ts
+++ b/packages/@lwc/shared/src/signals.ts
@@ -19,7 +19,15 @@ export function addTrustedSignal(signal: object) {
     trustedSignals?.add(signal);
 }
 
-export function isTrustedSignal(target: object): boolean {
+/**
+ * The legacy validation behavior was that this check should only
+ * be performed for runtimes that have provided a trustedSignals set.
+ * However, this resulted in a bug as all object values were
+ * being considered signals in environments where the trustedSignals
+ * set had not been defined. The runtime flag has been added as a killswitch
+ * in case the fix needs to be reverted.
+ */
+export function legacyIsTrustedSignal(target: object): boolean {
     if (!trustedSignals) {
         // The runtime didn't set a trustedSignals set
         // this check should only be performed for runtimes that care about filtering signals to track
@@ -28,3 +36,10 @@ export function isTrustedSignal(target: object): boolean {
     }
     return trustedSignals.has(target);
 }
+
+export function isTrustedSignal(target: object): boolean {
+    if (!trustedSignals) {
+        return false;
+    }
+    return trustedSignals.has(target);
+}
diff --git a/packages/@lwc/ssr-runtime/src/context.ts b/packages/@lwc/ssr-runtime/src/context.ts
index 280b2053ca..6bcf4961ee 100644
--- a/packages/@lwc/ssr-runtime/src/context.ts
+++ b/packages/@lwc/ssr-runtime/src/context.ts
@@ -8,6 +8,7 @@ import {
     type ContextProvidedCallback,
     type ContextBinding as IContextBinding,
     isTrustedContext,
+    legacyIsTrustedContext,
     getContextKeys,
     isUndefined,
     keys,
@@ -66,8 +67,11 @@ export function connectContext(le: LightningElement) {
     const { connectContext } = contextKeys;
 
     const enumerableKeys = keys(le);
+
     const contextfulKeys = ArrayFilter.call(enumerableKeys, (enumerableKey) =>
-        isTrustedContext((le as any)[enumerableKey])
+        lwcRuntimeFlags.ENABLE_LEGACY_SIGNAL_CONTEXT_VALIDATION
+            ? legacyIsTrustedContext((le as any)[enumerableKey])
+            : isTrustedContext((le as any)[enumerableKey])
     );
 
     if (contextfulKeys.length === 0) {
diff --git a/scripts/bundlesize/bundlesize.config.json b/scripts/bundlesize/bundlesize.config.json
index 941a42f360..624cd12230 100644
--- a/scripts/bundlesize/bundlesize.config.json
+++ b/scripts/bundlesize/bundlesize.config.json
@@ -2,7 +2,7 @@
     "files": [
         {
             "path": "packages/@lwc/engine-dom/dist/index.js",
-            "maxSize": "24.68KB"
+            "maxSize": "24.73KB"
         },
         {
             "path": "packages/@lwc/synthetic-shadow/dist/index.js",