diff --git a/.eslintrc.js b/.eslintrc.js
index 8b4cfa2db36a..2c69c6ecfedf 100644
--- a/.eslintrc.js
+++ b/.eslintrc.js
@@ -32,6 +32,16 @@ module.exports = {
     // our plugin :D
     //
 
+    '@typescript-eslint/ban-ts-comment': [
+      'error',
+      {
+        'ts-expect-error': 'allow-with-description',
+        'ts-ignore': true,
+        'ts-nocheck': true,
+        'ts-check': false,
+        minimumDescriptionLength: 5,
+      },
+    ],
     '@typescript-eslint/consistent-type-definitions': ['error', 'interface'],
     '@typescript-eslint/explicit-function-return-type': 'error',
     '@typescript-eslint/explicit-module-boundary-types': 'off',
diff --git a/packages/eslint-plugin/package.json b/packages/eslint-plugin/package.json
index 8ba7451b3889..c1b56bc9f0d8 100644
--- a/packages/eslint-plugin/package.json
+++ b/packages/eslint-plugin/package.json
@@ -43,6 +43,7 @@
   },
   "dependencies": {
     "@typescript-eslint/experimental-utils": "3.3.0",
+    "debug": "^4.1.1",
     "functional-red-black-tree": "^1.0.1",
     "regexpp": "^3.0.0",
     "semver": "^7.3.2",
diff --git a/packages/eslint-plugin/src/rules/await-thenable.ts b/packages/eslint-plugin/src/rules/await-thenable.ts
index 78b7ad129393..9858bad8ba2a 100644
--- a/packages/eslint-plugin/src/rules/await-thenable.ts
+++ b/packages/eslint-plugin/src/rules/await-thenable.ts
@@ -1,5 +1,4 @@
 import * as tsutils from 'tsutils';
-import * as ts from 'typescript';
 
 import * as util from '../util';
 
@@ -30,8 +29,8 @@ export default util.createRule({
         const type = checker.getTypeAtLocation(originalNode.expression);
 
         if (
-          !tsutils.isTypeFlagSet(type, ts.TypeFlags.Any) &&
-          !tsutils.isTypeFlagSet(type, ts.TypeFlags.Unknown) &&
+          !util.isTypeAnyType(type) &&
+          !util.isTypeUnknownType(type) &&
           !tsutils.isThenableType(checker, originalNode.expression, type)
         ) {
           context.report({
diff --git a/packages/eslint-plugin/src/rules/no-throw-literal.ts b/packages/eslint-plugin/src/rules/no-throw-literal.ts
index b85e0cc742db..67ba9e52ebe5 100644
--- a/packages/eslint-plugin/src/rules/no-throw-literal.ts
+++ b/packages/eslint-plugin/src/rules/no-throw-literal.ts
@@ -110,7 +110,8 @@ export default util.createRule({
         }
 
         if (
-          type.flags & (ts.TypeFlags.Any | ts.TypeFlags.Unknown) ||
+          util.isTypeAnyType(type) ||
+          util.isTypeUnknownType(type) ||
           isErrorLike(type)
         ) {
           return;
diff --git a/packages/eslint-plugin/src/rules/no-unnecessary-condition.ts b/packages/eslint-plugin/src/rules/no-unnecessary-condition.ts
index bed2ac82e55d..1147957a20cb 100644
--- a/packages/eslint-plugin/src/rules/no-unnecessary-condition.ts
+++ b/packages/eslint-plugin/src/rules/no-unnecessary-condition.ts
@@ -22,6 +22,8 @@ import {
   NullThrowsReasons,
   isMemberOrOptionalMemberExpression,
   isIdentifier,
+  isTypeAnyType,
+  isTypeUnknownType,
 } from '../util';
 
 // Truthiness utilities
@@ -181,13 +183,11 @@ export default createRule<Options, MessageId>({
       // Conditional is always necessary if it involves:
       //    `any` or `unknown` or a naked type parameter
       if (
-        unionTypeParts(type).some(part =>
-          isTypeFlagSet(
-            part,
-            ts.TypeFlags.Any |
-              ts.TypeFlags.Unknown |
-              ts.TypeFlags.TypeParameter,
-          ),
+        unionTypeParts(type).some(
+          part =>
+            isTypeAnyType(part) ||
+            isTypeUnknownType(part) ||
+            isTypeFlagSet(part, ts.TypeFlags.TypeParameter),
         )
       ) {
         return;
@@ -214,7 +214,7 @@ export default createRule<Options, MessageId>({
       }
       const type = getNodeType(node);
       // Conditional is always necessary if it involves `any` or `unknown`
-      if (isTypeFlagSet(type, ts.TypeFlags.Any | ts.TypeFlags.Unknown)) {
+      if (isTypeAnyType(type) || isTypeUnknownType(type)) {
         return;
       }
       const messageId = isTypeFlagSet(type, ts.TypeFlags.Never)
@@ -469,8 +469,8 @@ export default createRule<Options, MessageId>({
         ? !isNullableOriginFromPrev(node)
         : true;
       return (
-        isTypeFlagSet(type, ts.TypeFlags.Any) ||
-        isTypeFlagSet(type, ts.TypeFlags.Unknown) ||
+        isTypeAnyType(type) ||
+        isTypeUnknownType(type) ||
         (isNullableType(type, { allowUndefined: true }) && isOwnNullable)
       );
     }
diff --git a/packages/eslint-plugin/src/rules/restrict-template-expressions.ts b/packages/eslint-plugin/src/rules/restrict-template-expressions.ts
index a3cbb0b6f3bf..a4756266ffca 100644
--- a/packages/eslint-plugin/src/rules/restrict-template-expressions.ts
+++ b/packages/eslint-plugin/src/rules/restrict-template-expressions.ts
@@ -72,7 +72,7 @@ export default util.createRule<Options, MessageId>({
         return true;
       }
 
-      if (options.allowAny && util.isTypeFlagSet(type, ts.TypeFlags.Any)) {
+      if (options.allowAny && util.isTypeAnyType(type)) {
         return true;
       }
 
diff --git a/packages/eslint-plugin/src/rules/strict-boolean-expressions.ts b/packages/eslint-plugin/src/rules/strict-boolean-expressions.ts
index df2b59e12ec8..747cbefb7ebe 100644
--- a/packages/eslint-plugin/src/rules/strict-boolean-expressions.ts
+++ b/packages/eslint-plugin/src/rules/strict-boolean-expressions.ts
@@ -325,8 +325,8 @@ export default util.createRule<Options, MessageId>({
       }
 
       if (
-        types.some(type =>
-          tsutils.isTypeFlagSet(type, ts.TypeFlags.Any | ts.TypeFlags.Unknown),
+        types.some(
+          type => util.isTypeAnyType(type) || util.isTypeUnknownType(type),
         )
       ) {
         variantTypes.add('any');
diff --git a/packages/eslint-plugin/src/util/types.ts b/packages/eslint-plugin/src/util/types.ts
index 08a67cd7e5d9..2bd7e1997392 100644
--- a/packages/eslint-plugin/src/util/types.ts
+++ b/packages/eslint-plugin/src/util/types.ts
@@ -1,3 +1,4 @@
+import debug from 'debug';
 import {
   isCallExpression,
   isJsxExpression,
@@ -13,6 +14,8 @@ import {
 } from 'tsutils';
 import * as ts from 'typescript';
 
+const log = debug('typescript-eslint:eslint-plugin:utils:types');
+
 /**
  * Checks if the given type is either an array type,
  * or a union made up solely of array types.
@@ -326,11 +329,24 @@ export function getTypeArguments(
   return type.typeArguments ?? [];
 }
 
+/**
+ * @returns true if the type is `unknown`
+ */
+export function isTypeUnknownType(type: ts.Type): boolean {
+  return isTypeFlagSet(type, ts.TypeFlags.Unknown);
+}
+
 /**
  * @returns true if the type is `any`
  */
 export function isTypeAnyType(type: ts.Type): boolean {
-  return isTypeFlagSet(type, ts.TypeFlags.Any);
+  if (isTypeFlagSet(type, ts.TypeFlags.Any)) {
+    if (type.intrinsicName === 'error') {
+      log('Found an "error" any type');
+    }
+    return true;
+  }
+  return false;
 }
 
 /**
diff --git a/packages/eslint-plugin/typings/typescript.d.ts b/packages/eslint-plugin/typings/typescript.d.ts
index 7c9089158b4b..73304155ee74 100644
--- a/packages/eslint-plugin/typings/typescript.d.ts
+++ b/packages/eslint-plugin/typings/typescript.d.ts
@@ -23,4 +23,11 @@ declare module 'typescript' {
      */
     getTypeOfPropertyOfType(type: Type, propertyName: string): Type | undefined;
   }
+
+  interface Type {
+    /**
+     * If the type is `any`, and this is set to "error", then TS was unable to resolve the type
+     */
+    intrinsicName?: string;
+  }
 }