diff --git a/browser-versions.json b/browser-versions.json
index 4e3334648db7..beec05263965 100644
--- a/browser-versions.json
+++ b/browser-versions.json
@@ -1,4 +1,4 @@
 {
-  "chrome:beta": "98.0.4758.80",
+  "chrome:beta": "99.0.4844.27",
   "chrome:stable": "98.0.4758.80"
 }
diff --git a/packages/driver/src/cy/chai/inspect.ts b/packages/driver/src/cy/chai/inspect.ts
index 512336709ff4..5dfccd83fdc0 100644
--- a/packages/driver/src/cy/chai/inspect.ts
+++ b/packages/driver/src/cy/chai/inspect.ts
@@ -54,6 +54,18 @@ export function create (chai) {
       typeof object.nodeName === 'string'
   }
 
+  // We can't just check if object instanceof ShadowRoot, because it might be the document of an iframe,
+  // which in Chrome 99+ is a separate class, and instanceof ShadowRoot returns false.
+  const isShadowRoot = function (object) {
+    return isDOMElement(object.host) && object.host.shadowRoot === object
+  }
+
+  // We can't just check if object instanceof Document, because it might be the document of an iframe,
+  // which in Chrome 99+ is a separate class, and instanceof Document returns false.
+  const isDocument = function (object) {
+    return object.defaultView && object.defaultView === object.defaultView.window
+  }
+
   let formatValueHook
 
   const setFormatValueHook = (fn) => formatValueHook = fn
@@ -124,6 +136,14 @@ export function create (chai) {
       }
     }
 
+    if (isShadowRoot(value)) {
+      return value.innerHTML
+    }
+
+    if (isDocument(value)) {
+      return value.documentElement.outerHTML
+    }
+
     // Look up the keys of the object.
     let visibleKeys = getEnumerableProperties(value)
     let keys = ctx.showHidden ? getProperties(value) : visibleKeys
diff --git a/packages/driver/src/cypress/stack_utils.ts b/packages/driver/src/cypress/stack_utils.ts
index 0a3d2a188d3d..4b9f771e3224 100644
--- a/packages/driver/src/cypress/stack_utils.ts
+++ b/packages/driver/src/cypress/stack_utils.ts
@@ -139,13 +139,21 @@ const captureUserInvocationStack = (ErrorConstructor, userInvocationStack?) => {
   if (!userInvocationStack) {
     const newErr = new ErrorConstructor('userInvocationStack')
 
+    userInvocationStack = newErr.stack
+
     // if browser natively supports Error.captureStackTrace, use it (chrome) (must be bound)
     // otherwise use our polyfill on top.Error
     const captureStackTrace = ErrorConstructor.captureStackTrace ? ErrorConstructor.captureStackTrace.bind(ErrorConstructor) : Error.captureStackTrace
 
     captureStackTrace(newErr, captureUserInvocationStack)
 
-    userInvocationStack = newErr.stack
+    // On Chrome 99+, captureStackTrace strips away the whole stack,
+    // leaving nothing beyond the error message. If we get back a single line
+    // (just the error message with no stack trace), then use the original value
+    // instead of the trimmed one.
+    if (newErr.stack.match('\n')) {
+      userInvocationStack = newErr.stack
+    }
   }
 
   userInvocationStack = normalizedUserInvocationStack(userInvocationStack)