diff --git a/lib/internal/util/comparisons.js b/lib/internal/util/comparisons.js
index d86e59adae9880..8a9b4128c2efdc 100644
--- a/lib/internal/util/comparisons.js
+++ b/lib/internal/util/comparisons.js
@@ -43,6 +43,8 @@ const {
   isSymbolObject,
   isFloat32Array,
   isFloat64Array,
+  isKeyObject,
+  isCryptoKey,
 } = types;
 const {
   constants: {
@@ -60,6 +62,8 @@ const kIsArray = 1;
 const kIsSet = 2;
 const kIsMap = 3;
 
+let kKeyObject;
+
 // Check if they have the same source and flags
 function areSimilarRegExps(a, b) {
   return a.source === b.source &&
@@ -249,6 +253,20 @@ function innerDeepEqual(val1, val2, strict, memos) {
              isNativeError(val2) ||
              val2 instanceof Error) {
     return false;
+  } else if (isKeyObject(val1)) {
+    if (!isKeyObject(val2) || !val1.equals(val2)) {
+      return false;
+    }
+  } else if (isCryptoKey(val1)) {
+    kKeyObject ??= require('internal/crypto/util').kKeyObject;
+    if (!isCryptoKey(val2) ||
+      val1.extractable !== val2.extractable ||
+      !innerDeepEqual(val1.algorithm, val2.algorithm, strict, memos) ||
+      !innerDeepEqual(val1.usages, val2.usages, strict, memos) ||
+      !innerDeepEqual(val1[kKeyObject], val2[kKeyObject], strict, memos)
+    ) {
+      return false;
+    }
   }
   return keyCheck(val1, val2, strict, memos, kNoIterator);
 }
diff --git a/test/parallel/test-assert-deep.js b/test/parallel/test-assert-deep.js
index f7489993aa60ba..f147be1b41f2a8 100644
--- a/test/parallel/test-assert-deep.js
+++ b/test/parallel/test-assert-deep.js
@@ -1,6 +1,6 @@
 'use strict';
 
-require('../common');
+const common = require('../common');
 const assert = require('assert');
 const util = require('util');
 const { AssertionError } = assert;
@@ -1220,3 +1220,60 @@ assert.throws(
 
   assertNotDeepOrStrict(a, b);
 }
+
+// eslint-disable-next-line node-core/crypto-check
+if (common.hasCrypto) {
+  const crypto = require('crypto');
+  const { subtle } = globalThis.crypto;
+
+  {
+    const a = crypto.createSecretKey(Buffer.alloc(1, 0));
+    const b = crypto.createSecretKey(Buffer.alloc(1, 1));
+
+    assertNotDeepOrStrict(a, b);
+  }
+
+  {
+    const a = crypto.createSecretKey(Buffer.alloc(0));
+    const b = crypto.createSecretKey(Buffer.alloc(0));
+
+    assertDeepAndStrictEqual(a, b);
+  }
+
+  (async () => {
+    {
+      const a = await subtle.importKey('raw', Buffer.alloc(1, 0), { name: 'HMAC', hash: 'SHA-256' }, true, ['sign']);
+      const b = await subtle.importKey('raw', Buffer.alloc(1, 1), { name: 'HMAC', hash: 'SHA-256' }, true, ['sign']);
+
+      assertNotDeepOrStrict(a, b);
+    }
+
+    {
+      const a = await subtle.importKey('raw', Buffer.alloc(1), { name: 'HMAC', hash: 'SHA-256' }, true, ['sign']);
+      const b = await subtle.importKey('raw', Buffer.alloc(1), { name: 'HMAC', hash: 'SHA-256' }, false, ['sign']);
+
+      assertNotDeepOrStrict(a, b);
+    }
+
+    {
+      const a = await subtle.importKey('raw', Buffer.alloc(1), { name: 'HMAC', hash: 'SHA-256' }, true, ['sign']);
+      const b = await subtle.importKey('raw', Buffer.alloc(1), { name: 'HMAC', hash: 'SHA-384' }, true, ['sign']);
+
+      assertNotDeepOrStrict(a, b);
+    }
+
+    {
+      const a = await subtle.importKey('raw', Buffer.alloc(1), { name: 'HMAC', hash: 'SHA-256' }, true, ['sign']);
+      const b = await subtle.importKey('raw', Buffer.alloc(1), { name: 'HMAC', hash: 'SHA-256' }, true, ['verify']);
+
+      assertNotDeepOrStrict(a, b);
+    }
+
+    {
+      const a = await subtle.importKey('raw', Buffer.alloc(1), { name: 'HMAC', hash: 'SHA-256' }, true, ['sign']);
+      const b = await subtle.importKey('raw', Buffer.alloc(1), { name: 'HMAC', hash: 'SHA-256' }, true, ['sign']);
+
+      assertDeepAndStrictEqual(a, b);
+    }
+  })().then(common.mustCall());
+}