diff --git a/packages/expect/package.json b/packages/expect/package.json
index f712b10e53e3..d2a5cfea10dd 100644
--- a/packages/expect/package.json
+++ b/packages/expect/package.json
@@ -36,7 +36,7 @@
   "dependencies": {
     "@vitest/spy": "workspace:*",
     "@vitest/utils": "workspace:*",
-    "chai": "^4.3.10"
+    "chai": "^5.0.3"
   },
   "devDependencies": {
     "@types/chai": "4.3.6",
diff --git a/packages/expect/src/jest-extend.ts b/packages/expect/src/jest-extend.ts
index 27c53f843e71..bbe27df36ddd 100644
--- a/packages/expect/src/jest-extend.ts
+++ b/packages/expect/src/jest-extend.ts
@@ -1,4 +1,4 @@
-import { util } from 'chai'
+import { use, util } from 'chai'
 import type {
   ChaiPlugin,
   ExpectStatic,
@@ -55,8 +55,8 @@ class JestExtendError extends Error {
   }
 }
 
-function JestExtendPlugin(expect: ExpectStatic, matchers: MatchersObject): ChaiPlugin {
-  return (c, utils) => {
+function JestExtendPlugin(c: Chai.ChaiStatic, expect: ExpectStatic, matchers: MatchersObject): ChaiPlugin {
+  return (_, utils) => {
     Object.entries(matchers).forEach(([expectAssertionName, expectAssertion]) => {
       function expectWrapper(this: Chai.AssertionStatic & Chai.Assertion, ...args: any[]) {
         const { state, isNot, obj } = getMatcherState(this, expect)
@@ -139,6 +139,6 @@ function JestExtendPlugin(expect: ExpectStatic, matchers: MatchersObject): ChaiP
 
 export const JestExtend: ChaiPlugin = (chai, utils) => {
   utils.addMethod(chai.expect, 'extend', (expect: ExpectStatic, expects: MatchersObject) => {
-    chai.use(JestExtendPlugin(expect, expects))
+    use(JestExtendPlugin(chai, expect, expects))
   })
 }
diff --git a/packages/vitest/package.json b/packages/vitest/package.json
index e2a7924b667d..2af428bd6eff 100644
--- a/packages/vitest/package.json
+++ b/packages/vitest/package.json
@@ -152,7 +152,7 @@
     "@vitest/snapshot": "workspace:*",
     "@vitest/spy": "workspace:*",
     "@vitest/utils": "workspace:*",
-    "chai": "^4.3.10",
+    "chai": "^5.1.0",
     "debug": "^4.3.4",
     "execa": "^8.0.1",
     "magic-string": "^0.30.5",
diff --git a/pnpm-lock.yaml b/pnpm-lock.yaml
index 56a9f2b207a0..13bc6e06b69a 100644
--- a/pnpm-lock.yaml
+++ b/pnpm-lock.yaml
@@ -634,8 +634,8 @@ importers:
         specifier: workspace:*
         version: link:../utils
       chai:
-        specifier: ^4.3.10
-        version: 4.3.10
+        specifier: ^5.0.3
+        version: 5.0.3
     devDependencies:
       '@types/chai':
         specifier: 4.3.6
@@ -876,8 +876,8 @@ importers:
         specifier: workspace:*
         version: link:../utils
       chai:
-        specifier: ^4.3.10
-        version: 4.3.10
+        specifier: ^5.1.0
+        version: 5.1.0
       debug:
         specifier: ^4.3.4
         version: 4.3.4(supports-color@8.1.1)
@@ -7375,6 +7375,12 @@ packages:
 
   /assertion-error@1.1.0:
     resolution: {integrity: sha512-jgsaNduz+ndvGyFt3uSuWqvy4lCnIJiovtouQN5JZHOKCS2QuhEdbcQHFhVksz2N2U9hXJo8odG7ETyWlEeuDw==}
+    dev: true
+
+  /assertion-error@2.0.1:
+    resolution: {integrity: sha512-Izi8RQcffqCeNVgFigKli1ssklIbpHnCYc6AknXGYoB6grJqyeby7jv12JUQgmTAnIDnbck1uxksT4dzN3PWBA==}
+    engines: {node: '>=12'}
+    dev: false
 
   /ast-types@0.13.4:
     resolution: {integrity: sha512-x1FCFnFifvYDDzTaLII71vG5uvDwgtmDTEVWAxrgeiR8VjMONcCXJx7E+USjDtHlwFmt9MysbqgF9b9Vjr6w+w==}
@@ -7806,17 +7812,26 @@ packages:
       type-detect: 1.0.0
     dev: true
 
-  /chai@4.3.10:
-    resolution: {integrity: sha512-0UXG04VuVbruMUYbJ6JctvH0YnC/4q3/AkT18q4NaITo91CUm0liMS9VqzT9vZhVQ/1eqPanMWjBM+Juhfb/9g==}
-    engines: {node: '>=4'}
+  /chai@5.0.3:
+    resolution: {integrity: sha512-wKGCtYv2kVY5WEjKqQ3fSIZWtTFveZCtzinhTZbx3/trVkxefiwovhpU9kRVCwxvKKCEjTWXPdM1/T7zPoDgow==}
+    engines: {node: '>=12'}
     dependencies:
-      assertion-error: 1.1.0
-      check-error: 1.0.3
-      deep-eql: 4.1.3
-      get-func-name: 2.0.2
-      loupe: 2.3.6
-      pathval: 1.1.1
-      type-detect: 4.0.8
+      assertion-error: 2.0.1
+      check-error: 2.0.0
+      deep-eql: 5.0.1
+      loupe: 3.1.0
+      pathval: 2.0.0
+    dev: false
+
+  /chai@5.1.0:
+    resolution: {integrity: sha512-kDZ7MZyM6Q1DhR9jy7dalKohXQ2yrlXkk59CR52aRKxJrobmlBNqnFQxX9xOX8w+4mz8SYlKJa/7D7ddltFXCw==}
+    engines: {node: '>=12'}
+    dependencies:
+      assertion-error: 2.0.1
+      check-error: 2.0.0
+      deep-eql: 5.0.1
+      loupe: 3.1.0
+      pathval: 2.0.0
     dev: false
 
   /chainsaw@0.1.0:
@@ -7880,10 +7895,9 @@ packages:
     resolution: {integrity: sha512-mT8iDcrh03qDGRRmoA2hmBJnxpllMR+0/0qlzjqZES6NdiWDcZkCNAk4rPFZ9Q85r27unkiNNg8ZOiwZXBHwcA==}
     dev: true
 
-  /check-error@1.0.3:
-    resolution: {integrity: sha512-iKEoDYaRmd1mxM90a2OEfWhjsjPpYPuQ+lMYsoxB126+t8fw7ySEO48nmDg5COTjxDI65/Y2OWpeEHk3ZOe8zg==}
-    dependencies:
-      get-func-name: 2.0.2
+  /check-error@2.0.0:
+    resolution: {integrity: sha512-tjLAOBHKVxtPoHe/SA7kNOMvhCRdCJ3vETdeY0RuAc9popf+hyaSV6ZEg9hr4cpWF7jmo/JSWEnLDrnijS9Tog==}
+    engines: {node: '>= 16'}
     dev: false
 
   /check-more-types@2.24.0:
@@ -8640,11 +8654,9 @@ packages:
       type-detect: 0.1.1
     dev: true
 
-  /deep-eql@4.1.3:
-    resolution: {integrity: sha512-WaEtAOpRA1MQ0eohqZjpGD8zdI0Ovsm8mmFhaDN8dvDZzyoUMcYDnf5Y6iu7HTXxf8JDS23qWa4a+hKCDyOPzw==}
+  /deep-eql@5.0.1:
+    resolution: {integrity: sha512-nwQCf6ne2gez3o1MxWifqkciwt0zhl0LO1/UwVu4uMBuPmflWM4oQ70XMqHqnBJA+nhzncaqL9HVL6KkHJ28lw==}
     engines: {node: '>=6'}
-    dependencies:
-      type-detect: 4.0.8
     dev: false
 
   /deep-equal@2.2.1:
@@ -12071,14 +12083,14 @@ packages:
     dependencies:
       js-tokens: 4.0.0
 
-  /loupe@2.3.6:
-    resolution: {integrity: sha512-RaPMZKiMy8/JruncMU5Bt6na1eftNoo++R4Y+N2FrxkDVTrGvcyzFTsaGif4QTeKESheMGegbhw6iUAq+5A8zA==}
+  /loupe@2.3.7:
+    resolution: {integrity: sha512-zSMINGVYkdpYSOBmLi0D1Uo7JU9nVdQKrHxC8eYlV+9YKK9WePqAlL7lSlorG/U2Fw1w0hTBmaa/jrQ3UbPHtA==}
     dependencies:
       get-func-name: 2.0.2
     dev: false
 
-  /loupe@2.3.7:
-    resolution: {integrity: sha512-zSMINGVYkdpYSOBmLi0D1Uo7JU9nVdQKrHxC8eYlV+9YKK9WePqAlL7lSlorG/U2Fw1w0hTBmaa/jrQ3UbPHtA==}
+  /loupe@3.1.0:
+    resolution: {integrity: sha512-qKl+FrLXUhFuHUoDJG7f8P8gEMHq9NFS0c6ghXG1J0rldmZFQZoNVv/vyirE9qwCIhWZDsvEFd1sbFu3GvRQFg==}
     dependencies:
       get-func-name: 2.0.2
     dev: false
@@ -13268,8 +13280,9 @@ packages:
     resolution: {integrity: sha512-whLdWMYL2TwI08hn8/ZqAbrVemu0LNaNNJZX73O6qaIdCTfXutsLhMkjdENX0qhsQ9uIimo4/aQOmXkoon2nDQ==}
     dev: true
 
-  /pathval@1.1.1:
-    resolution: {integrity: sha512-Dp6zGqpTdETdR63lehJYPeIOqpiNBNtc7BpWSLrOje7UaIsE5aY92r/AunQA7rsXvet3lrJ3JnZX29UPTKXyKQ==}
+  /pathval@2.0.0:
+    resolution: {integrity: sha512-vE7JKRyES09KiunauX7nd2Q9/L7lhok4smP9RZTDeD4MVs72Dp2qNFVz39Nz5a0FVEW0BJR6C0DYrq6unoziZA==}
+    engines: {node: '>= 14.16'}
     dev: false
 
   /pend@1.2.0:
@@ -15451,6 +15464,7 @@ packages:
   /type-detect@4.0.8:
     resolution: {integrity: sha512-0fr/mIH1dlO+x7TlcMy+bIDqKPsw/70tVyeHW787goQjhmqaZe10uwLujubK9q9Lg6Fiho1KUKDYz0Z7k7g5/g==}
     engines: {node: '>=4'}
+    dev: true
 
   /type-fest@0.16.0:
     resolution: {integrity: sha512-eaBzG6MxNzEn9kiwvtre90cXaNLkmadMWa1zQMs3XORCXNbsH/OewwbxC5ia9dCxIxnTAsSxXJaa/p5y8DlvJg==}
diff --git a/test/reporters/tests/__snapshots__/html.test.ts.snap b/test/reporters/tests/__snapshots__/html.test.ts.snap
index 8f765c937cfe..58d0059bfcb5 100644
--- a/test/reporters/tests/__snapshots__/html.test.ts.snap
+++ b/test/reporters/tests/__snapshots__/html.test.ts.snap
@@ -55,6 +55,7 @@ exports[`html reporter > resolves to "failing" status for test file "json-fail"
                 "message": "expected 2 to deeply equal 1",
                 "name": "AssertionError",
                 "nameStr": "AssertionError",
+                "ok": false,
                 "operator": "strictEqual",
                 "showDiff": true,
                 "stack": "AssertionError: expected 2 to deeply equal 1",