diff --git a/packages/eslint-plugin/docs/rules/prefer-optional-chain.mdx b/packages/eslint-plugin/docs/rules/prefer-optional-chain.mdx
index 47fcec6d598f..ee7aa6abf42f 100644
--- a/packages/eslint-plugin/docs/rules/prefer-optional-chain.mdx
+++ b/packages/eslint-plugin/docs/rules/prefer-optional-chain.mdx
@@ -265,7 +265,7 @@ When this option is `true` the rule will skip operands that are not typed with `
 
 <TabItem value="❌ Incorrect for `requireNullish: true`">
 
-```ts option='{ "requireNullish": true }' skipValidation
+```ts option='{ "requireNullish": true }'
 declare const thing1: string | null;
 thing1 && thing1.toString();
 ```
diff --git a/packages/eslint-plugin/src/rules/prefer-optional-chain-utils/analyzeChain.ts b/packages/eslint-plugin/src/rules/prefer-optional-chain-utils/analyzeChain.ts
index 5ebb8e02ae51..24ba787dec77 100644
--- a/packages/eslint-plugin/src/rules/prefer-optional-chain-utils/analyzeChain.ts
+++ b/packages/eslint-plugin/src/rules/prefer-optional-chain-utils/analyzeChain.ts
@@ -20,6 +20,7 @@ import {
   NullThrowsReasons,
   OperatorPrecedence,
 } from '../../util';
+import { checkNullishAndReport } from './checkNullishAndReport';
 import { compareNodes, NodeComparisonResult } from './compareNodes';
 import type { ValidOperand } from './gatherLogicalOperands';
 import { NullishComparisonType } from './gatherLogicalOperands';
@@ -493,20 +494,26 @@ export function analyzeChain(
   ): void => {
     if (subChain.length > 1) {
       const subChainFlat = subChain.flat();
-      context.report({
-        messageId: 'preferOptionalChain',
-        loc: {
-          start: subChainFlat[0].node.loc.start,
-          end: subChainFlat[subChainFlat.length - 1].node.loc.end,
+      checkNullishAndReport(
+        context,
+        parserServices,
+        options,
+        subChainFlat.slice(0, -1).map(({ node }) => node),
+        {
+          messageId: 'preferOptionalChain',
+          loc: {
+            start: subChainFlat[0].node.loc.start,
+            end: subChainFlat[subChainFlat.length - 1].node.loc.end,
+          },
+          ...getFixer(
+            context.sourceCode,
+            parserServices,
+            operator,
+            options,
+            subChainFlat,
+          ),
         },
-        ...getFixer(
-          context.sourceCode,
-          parserServices,
-          operator,
-          options,
-          subChainFlat,
-        ),
-      });
+      );
     }
 
     // we've reached the end of a chain of logical expressions
diff --git a/packages/eslint-plugin/src/rules/prefer-optional-chain-utils/checkNullishAndReport.ts b/packages/eslint-plugin/src/rules/prefer-optional-chain-utils/checkNullishAndReport.ts
new file mode 100644
index 000000000000..404b3736040a
--- /dev/null
+++ b/packages/eslint-plugin/src/rules/prefer-optional-chain-utils/checkNullishAndReport.ts
@@ -0,0 +1,38 @@
+import { isTypeFlagSet } from '@typescript-eslint/type-utils';
+import type {
+  ParserServicesWithTypeInformation,
+  TSESTree,
+} from '@typescript-eslint/utils';
+import type {
+  ReportDescriptor,
+  RuleContext,
+} from '@typescript-eslint/utils/ts-eslint';
+import { unionTypeParts } from 'ts-api-utils';
+import * as ts from 'typescript';
+
+import type {
+  PreferOptionalChainMessageIds,
+  PreferOptionalChainOptions,
+} from './PreferOptionalChainOptions';
+
+export function checkNullishAndReport(
+  context: RuleContext<
+    PreferOptionalChainMessageIds,
+    [PreferOptionalChainOptions]
+  >,
+  parserServices: ParserServicesWithTypeInformation,
+  { requireNullish }: PreferOptionalChainOptions,
+  maybeNullishNodes: TSESTree.Expression[],
+  descriptor: ReportDescriptor<PreferOptionalChainMessageIds>,
+): void {
+  if (
+    !requireNullish ||
+    maybeNullishNodes.some(node =>
+      unionTypeParts(parserServices.getTypeAtLocation(node)).some(t =>
+        isTypeFlagSet(t, ts.TypeFlags.Null | ts.TypeFlags.Undefined),
+      ),
+    )
+  ) {
+    context.report(descriptor);
+  }
+}
diff --git a/packages/eslint-plugin/src/rules/prefer-optional-chain-utils/gatherLogicalOperands.ts b/packages/eslint-plugin/src/rules/prefer-optional-chain-utils/gatherLogicalOperands.ts
index 4b90947da0ed..54c44f4edda9 100644
--- a/packages/eslint-plugin/src/rules/prefer-optional-chain-utils/gatherLogicalOperands.ts
+++ b/packages/eslint-plugin/src/rules/prefer-optional-chain-utils/gatherLogicalOperands.ts
@@ -90,10 +90,6 @@ function isValidFalseBooleanCheckType(
     }
   }
 
-  if (options.requireNullish === true) {
-    return types.some(t => isTypeFlagSet(t, NULLISH_FLAGS));
-  }
-
   let allowedFlags = NULLISH_FLAGS | ts.TypeFlags.Object;
   if (options.checkAny === true) {
     allowedFlags |= ts.TypeFlags.Any;
diff --git a/packages/eslint-plugin/src/rules/prefer-optional-chain.ts b/packages/eslint-plugin/src/rules/prefer-optional-chain.ts
index 605045b99fd2..18acdd72caf2 100644
--- a/packages/eslint-plugin/src/rules/prefer-optional-chain.ts
+++ b/packages/eslint-plugin/src/rules/prefer-optional-chain.ts
@@ -10,6 +10,7 @@ import {
   OperatorPrecedence,
 } from '../util';
 import { analyzeChain } from './prefer-optional-chain-utils/analyzeChain';
+import { checkNullishAndReport } from './prefer-optional-chain-utils/checkNullishAndReport';
 import type { ValidOperand } from './prefer-optional-chain-utils/gatherLogicalOperands';
 import {
   gatherLogicalOperands,
@@ -141,9 +142,9 @@ export default createRule<
 
           return leftPrecedence < OperatorPrecedence.LeftHandSide;
         }
-        context.report({
-          node: parentNode,
+        checkNullishAndReport(context, parserServices, options, [leftNode], {
           messageId: 'preferOptionalChain',
+          node: parentNode,
           suggest: [
             {
               messageId: 'optionalChainSuggest',
diff --git a/packages/eslint-plugin/tests/docs-eslint-output-snapshots/prefer-optional-chain.shot b/packages/eslint-plugin/tests/docs-eslint-output-snapshots/prefer-optional-chain.shot
index 36130171307f..980b3f8058df 100644
--- a/packages/eslint-plugin/tests/docs-eslint-output-snapshots/prefer-optional-chain.shot
+++ b/packages/eslint-plugin/tests/docs-eslint-output-snapshots/prefer-optional-chain.shot
@@ -202,6 +202,7 @@ Options: { "requireNullish": true }
 
 declare const thing1: string | null;
 thing1 && thing1.toString();
+~~~~~~~~~~~~~~~~~~~~~~~~~~~ Prefer using an optional chain expression instead, as it's more concise and easier to read.
 "
 `;
 
diff --git a/packages/eslint-plugin/tests/rules/prefer-optional-chain/prefer-optional-chain.test.ts b/packages/eslint-plugin/tests/rules/prefer-optional-chain/prefer-optional-chain.test.ts
index 99b6362132cf..55ab44f1a069 100644
--- a/packages/eslint-plugin/tests/rules/prefer-optional-chain/prefer-optional-chain.test.ts
+++ b/packages/eslint-plugin/tests/rules/prefer-optional-chain/prefer-optional-chain.test.ts
@@ -815,22 +815,64 @@ describe('hand-crafted cases', () => {
           declare const x: string;
           x && x.length;
         `,
-        options: [
-          {
-            requireNullish: true,
-          },
-        ],
+        options: [{ requireNullish: true }],
+      },
+      {
+        code: `
+          declare const foo: string;
+          foo && foo.toString();
+        `,
+        options: [{ requireNullish: true }],
       },
       {
         code: `
           declare const x: string | number | boolean | object;
           x && x.toString();
         `,
-        options: [
-          {
-            requireNullish: true,
-          },
-        ],
+        options: [{ requireNullish: true }],
+      },
+      {
+        code: `
+          declare const foo: { bar: string };
+          foo && foo.bar && foo.bar.toString();
+        `,
+        options: [{ requireNullish: true }],
+      },
+      {
+        code: `
+          declare const foo: string;
+          foo && foo.toString() && foo.toString();
+        `,
+        options: [{ requireNullish: true }],
+      },
+      {
+        code: `
+          declare const foo: { bar: string };
+          foo && foo.bar && foo.bar.toString() && foo.bar.toString();
+        `,
+        options: [{ requireNullish: true }],
+      },
+      {
+        code: `
+          declare const foo1: { bar: string | null };
+          foo1 && foo1.bar;
+        `,
+        options: [{ requireNullish: true }],
+      },
+      {
+        code: `
+          declare const foo: string;
+          (foo || {}).toString();
+        `,
+        options: [{ requireNullish: true }],
+      },
+
+      {
+        code: `
+          declare const foo: string | null;
+          (foo || 'a' || {}).toString();
+        `,
+        options: [{ requireNullish: true }],
       },
       {
         code: `
@@ -1895,6 +1937,80 @@ describe('hand-crafted cases', () => {
         ],
       },
 
+      // requireNullish
+      {
+        code: `
+          declare const thing1: string | null;
+          thing1 && thing1.toString();
+        `,
+        options: [{ requireNullish: true }],
+        errors: [{ messageId: 'preferOptionalChain' }],
+      },
+      {
+        code: `
+          declare const thing1: string | null;
+          thing1 && thing1.toString() && true;
+        `,
+        options: [{ requireNullish: true }],
+        errors: [{ messageId: 'preferOptionalChain' }],
+      },
+      {
+        code: `
+          declare const foo: string | null;
+          foo && foo.toString() && foo.toString();
+        `,
+        options: [{ requireNullish: true }],
+        errors: [{ messageId: 'preferOptionalChain' }],
+      },
+      {
+        code: `
+          declare const foo: { bar: string | null | undefined } | null | undefined;
+          foo && foo.bar && foo.bar.toString();
+        `,
+        output: `
+          declare const foo: { bar: string | null | undefined } | null | undefined;
+          foo?.bar?.toString();
+        `,
+        options: [{ requireNullish: true }],
+        errors: [{ messageId: 'preferOptionalChain' }],
+      },
+      {
+        code: `
+          declare const foo: { bar: string | null | undefined } | null | undefined;
+          foo && foo.bar && foo.bar.toString() && foo.bar.toString();
+        `,
+        output: `
+          declare const foo: { bar: string | null | undefined } | null | undefined;
+          foo?.bar?.toString() && foo.bar.toString();
+        `,
+        options: [{ requireNullish: true }],
+        errors: [{ messageId: 'preferOptionalChain' }],
+      },
+      {
+        code: `
+          declare const foo: string | null;
+          (foo || {}).toString();
+        `,
+        options: [{ requireNullish: true }],
+        errors: [{ messageId: 'preferOptionalChain' }],
+      },
+      {
+        code: `
+          declare const foo: string;
+          (foo || undefined || {}).toString();
+        `,
+        options: [{ requireNullish: true }],
+        errors: [{ messageId: 'preferOptionalChain' }],
+      },
+      {
+        code: `
+          declare const foo: string | null;
+          (foo || undefined || {}).toString();
+        `,
+        options: [{ requireNullish: true }],
+        errors: [{ messageId: 'preferOptionalChain' }],
+      },
+
       // allowPotentiallyUnsafeFixesThatModifyTheReturnTypeIKnowWhatImDoing
       {
         code: `