diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index 84b111555df7e..c66b079df1cf1 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -8,6 +8,7 @@ import {
     addSyntheticLeadingComment,
     AliasDeclarationNode,
     AllAccessorDeclarations,
+    AllowRequireESM,
     AmbientModuleDeclaration,
     and,
     AnonymousType,
@@ -138,6 +139,7 @@ import {
     Decorator,
     deduplicate,
     DefaultClause,
+    DefaultIsModuleExports,
     defaultMaximumTruncationLength,
     DeferredTypeReference,
     DeleteExpression,
@@ -245,6 +247,7 @@ import {
     GetAccessorDeclaration,
     getAliasDeclarationFromName,
     getAllJSDocTags,
+    getAllowRequireESM,
     getAllowSyntheticDefaultImports,
     getAncestor,
     getAssignedExpandoInitializer,
@@ -268,6 +271,7 @@ import {
     getDeclarationsOfKind,
     getDeclaredExpandoInitializer,
     getDecorators,
+    getDefaultIsModuleExports,
     getDirectoryPath,
     getEffectiveBaseTypeNode,
     getEffectiveConstraintOfTypeParameter,
@@ -3634,7 +3638,9 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
         const usageMode = file && getEmitSyntaxForModuleSpecifierExpression(usage);
         if (file && usageMode !== undefined) {
             const targetMode = host.getImpliedNodeFormatForEmit(file);
-            if (usageMode === ModuleKind.ESNext && targetMode === ModuleKind.CommonJS && ModuleKind.Node16 <= moduleKind && moduleKind <= ModuleKind.NodeNext) {
+            const defaultIsModuleExports = getDefaultIsModuleExports(compilerOptions);
+            const usesNodeLikeInteropRules = DefaultIsModuleExports.Node16 <= defaultIsModuleExports && defaultIsModuleExports <= DefaultIsModuleExports.NodeNext;
+            if (usageMode === ModuleKind.ESNext && targetMode !== ModuleKind.ESNext && usesNodeLikeInteropRules) {
                 // In Node.js, CommonJS modules always have a synthetic default when imported into ESM
                 return true;
             }
@@ -3649,6 +3655,10 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
         }
         // Declaration files (and ambient modules)
         if (!file || file.isDeclarationFile) {
+            // Unambiguously ESM files do not have a synthetic default
+            if (file && host.getImpliedNodeFormatForEmit(file) === ModuleKind.ESNext) {
+                return false;
+            }
             // Definitely cannot have a synthetic default if they have a syntactic default member specified
             const defaultExportSymbol = resolveExportByName(moduleSymbol, InternalSymbolName.Default, /*sourceNode*/ undefined, /*dontResolveAlias*/ true); // Dont resolve alias because we want the immediately exported symbol's declaration
             if (defaultExportSymbol && some(defaultExportSymbol.declarations, isSyntacticDefault)) {
@@ -4571,7 +4581,9 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
         const mode = contextSpecifier && isStringLiteralLike(contextSpecifier)
             ? host.getModeForUsageLocation(currentSourceFile, contextSpecifier)
             : host.getDefaultResolutionModeForFile(currentSourceFile);
+        const importingFileIsJavaScript = isSourceFileJS(currentSourceFile);
         const moduleResolutionKind = getEmitModuleResolutionKind(compilerOptions);
+        const allowRequireESM = getAllowRequireESM(compilerOptions);
         const resolvedModule = host.getResolvedModule(currentSourceFile, moduleReference, mode)?.resolvedModule;
         const resolutionDiagnostic = resolvedModule && getResolutionDiagnostic(compilerOptions, resolvedModule, currentSourceFile);
         const sourceFile = resolvedModule
@@ -4607,12 +4619,13 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
                 if (resolvedModule.isExternalLibraryImport && !resolutionExtensionIsTSOrJson(resolvedModule.extension)) {
                     errorOnImplicitAnyModule(/*isError*/ false, errorNode, currentSourceFile, mode, resolvedModule, moduleReference);
                 }
-                if (moduleResolutionKind === ModuleResolutionKind.Node16 || moduleResolutionKind === ModuleResolutionKind.NodeNext) {
-                    const isSyncImport = (currentSourceFile.impliedNodeFormat === ModuleKind.CommonJS && !findAncestor(location, isImportCall)) || !!findAncestor(location, isImportEqualsDeclaration);
+                if (AllowRequireESM.Node16 <= allowRequireESM && allowRequireESM <= AllowRequireESM.NodeNext) {
+                    const isSyncImport = (host.getImpliedNodeFormatForEmit(currentSourceFile) === ModuleKind.CommonJS && !findAncestor(location, isImportCall))
+                        || !!findAncestor(location, n => isImportEqualsDeclaration(n) || importingFileIsJavaScript && isVariableDeclarationInitializedToBareOrAccessedRequire(n));
                     const overrideHost = findAncestor(location, l => isImportTypeNode(l) || isExportDeclaration(l) || isImportDeclaration(l)) as ImportTypeNode | ImportDeclaration | ExportDeclaration | undefined;
                     // An override clause will take effect for type-only imports and import types, and allows importing the types across formats, regardless of
                     // normal mode restrictions
-                    if (isSyncImport && sourceFile.impliedNodeFormat === ModuleKind.ESNext && !hasResolutionModeOverride(overrideHost)) {
+                    if (isSyncImport && host.getImpliedNodeFormatForEmit(sourceFile) === ModuleKind.ESNext && !hasResolutionModeOverride(overrideHost)) {
                         if (findAncestor(location, isImportEqualsDeclaration)) {
                             // ImportEquals in a ESM file resolving to another ESM file
                             error(errorNode, Diagnostics.Module_0_cannot_be_imported_using_this_construct_The_specifier_only_resolves_to_an_ES_module_which_cannot_be_imported_with_require_Use_an_ECMAScript_import_instead, moduleReference);
diff --git a/src/compiler/commandLineParser.ts b/src/compiler/commandLineParser.ts
index 52db793b070a8..7e9002ffcb739 100644
--- a/src/compiler/commandLineParser.ts
+++ b/src/compiler/commandLineParser.ts
@@ -1,4 +1,5 @@
 import {
+    AllowRequireESM,
     AlternateModeDiagnostics,
     append,
     arrayFrom,
@@ -23,6 +24,7 @@ import {
     createDiagnosticForNodeInSourceFile,
     createGetCanonicalFileName,
     Debug,
+    DefaultIsModuleExports,
     Diagnostic,
     DiagnosticArguments,
     DiagnosticMessage,
@@ -1196,6 +1198,33 @@ const commandOptionsWithoutBuild: CommandLineOption[] = [
         category: Diagnostics.Modules,
         description: Diagnostics.Conditions_to_set_in_addition_to_the_resolver_specific_defaults_when_resolving_imports,
     },
+    {
+        name: "defaultIsModuleExports",
+        type: new Map(Object.entries({
+            auto: DefaultIsModuleExports.Auto,
+            node16: DefaultIsModuleExports.Node16,
+            nodenext: DefaultIsModuleExports.NodeNext,
+        })),
+        affectsSemanticDiagnostics: true,
+        affectsBuildInfo: true,
+        category: Diagnostics.Modules,
+        description: Diagnostics.Specify_the_target_runtime_s_rules_for_default_imports_targeting_CommonJS_modules,
+        defaultValueDescription: Diagnostics.node16_when_module_is_node16_nodenext_when_module_is_nodenext_auto_otherwise,
+    },
+    {
+        name: "allowRequireESM",
+        type: new Map(Object.entries({
+            never: AllowRequireESM.Never,
+            always: AllowRequireESM.Always,
+            node16: AllowRequireESM.Node16,
+            nodenext: AllowRequireESM.NodeNext,
+        })),
+        affectsSemanticDiagnostics: true,
+        affectsBuildInfo: true,
+        category: Diagnostics.Modules,
+        description: Diagnostics.Specify_the_target_runtime_s_rules_for_CommonJS_require_calls_targeting_ECMAScript_modules,
+        defaultValueDescription: Diagnostics.node16_when_module_is_node16_nodenext_when_module_is_nodenext_always_otherwise,
+    },
 
     // Source Maps
     {
diff --git a/src/compiler/diagnosticMessages.json b/src/compiler/diagnosticMessages.json
index 1db3b8c70bc30..ed0097d151b2a 100644
--- a/src/compiler/diagnosticMessages.json
+++ b/src/compiler/diagnosticMessages.json
@@ -6392,6 +6392,14 @@
         "category": "Message",
         "code": 6805
     },
+    "Specify the target runtime's rules for default imports targeting CommonJS modules.": {
+        "category": "Message",
+        "code": 6806
+    },
+    "Specify the target runtime's rules for CommonJS 'require' calls targeting ECMAScript modules.": {
+        "category": "Message",
+        "code": 6807
+    },
 
     "one of:": {
         "category": "Message",
@@ -6521,6 +6529,14 @@
         "category": "Error",
         "code": 6931
     },
+    "'node16' when 'module' is 'node16'; 'nodenext' when 'module' is 'nodenext'; 'auto' otherwise.": {
+        "category": "Message",
+        "code": 6932
+    },
+    "'node16' when 'module' is 'node16'; 'nodenext' when 'module' is 'nodenext'; 'always' otherwise.": {
+        "category": "Message",
+        "code": 6933
+    },
 
     "Variable '{0}' implicitly has an '{1}' type.": {
         "category": "Error",
diff --git a/src/compiler/types.ts b/src/compiler/types.ts
index 1b737bd261363..c3b4d37532eac 100644
--- a/src/compiler/types.ts
+++ b/src/compiler/types.ts
@@ -7227,6 +7227,7 @@ export interface CompilerOptions {
     allowJs?: boolean;
     /** @internal */ allowNonTsExtensions?: boolean;
     allowArbitraryExtensions?: boolean;
+    allowRequireESM?: AllowRequireESM;
     allowSyntheticDefaultImports?: boolean;
     allowUmdGlobalAccess?: boolean;
     allowUnreachableCode?: boolean;
@@ -7254,6 +7255,7 @@ export interface CompilerOptions {
     declarationMap?: boolean;
     emitDeclarationOnly?: boolean;
     declarationDir?: string;
+    defaultIsModuleExports?: DefaultIsModuleExports;
     /** @internal */ diagnostics?: boolean;
     /** @internal */ extendedDiagnostics?: boolean;
     disableSizeLimit?: boolean;
@@ -7423,6 +7425,19 @@ export enum ModuleKind {
     Preserve = 200,
 }
 
+export enum DefaultIsModuleExports {
+    Auto = 1,
+    Node16 = 100,
+    NodeNext = 199,
+}
+
+export enum AllowRequireESM {
+    Never = 0,
+    Always = 1,
+    Node16 = 100,
+    NodeNext = 199,
+}
+
 export const enum JsxEmit {
     None = 0,
     Preserve = 1,
diff --git a/src/compiler/utilities.ts b/src/compiler/utilities.ts
index 655c35eacf576..4dd758ca57c3d 100644
--- a/src/compiler/utilities.ts
+++ b/src/compiler/utilities.ts
@@ -6,6 +6,7 @@ import {
     affectsDeclarationPathOptionDeclarations,
     affectsEmitOptionDeclarations,
     AllAccessorDeclarations,
+    AllowRequireESM,
     AmbientModuleDeclaration,
     AmpersandAmpersandEqualsToken,
     AnyImportOrBareOrAccessedRequire,
@@ -90,6 +91,7 @@ import {
     DeclarationWithTypeParameters,
     Decorator,
     DefaultClause,
+    DefaultIsModuleExports,
     DestructuringAssignment,
     Diagnostic,
     DiagnosticArguments,
@@ -8852,6 +8854,30 @@ export const computedOptions = createComputedCompilerOptions({
                         computedOptions.module.computeValue(compilerOptions) === ModuleKind.NodeNext ? ModuleDetectionKind.Force : ModuleDetectionKind.Auto);
         },
     },
+    defaultIsModuleExports: {
+        dependencies: ["module", "target"],
+        computeValue: (compilerOptions): DefaultIsModuleExports => {
+            if (compilerOptions.defaultIsModuleExports !== undefined) {
+                return compilerOptions.defaultIsModuleExports;
+            }
+            const moduleKind = computedOptions.module.computeValue(compilerOptions);
+            return moduleKind === ModuleKind.Node16 ? DefaultIsModuleExports.Node16 :
+                moduleKind === ModuleKind.NodeNext ? DefaultIsModuleExports.NodeNext :
+                DefaultIsModuleExports.Auto;
+        },
+    },
+    allowRequireESM: {
+        dependencies: ["module", "target"],
+        computeValue: (compilerOptions): AllowRequireESM => {
+            if (compilerOptions.allowRequireESM !== undefined) {
+                return compilerOptions.allowRequireESM;
+            }
+            const moduleKind = computedOptions.module.computeValue(compilerOptions);
+            return moduleKind === ModuleKind.Node16 ? AllowRequireESM.Node16 :
+                moduleKind === ModuleKind.NodeNext ? AllowRequireESM.NodeNext :
+                AllowRequireESM.Always;
+        },
+    },
     isolatedModules: {
         dependencies: ["verbatimModuleSyntax"],
         computeValue: compilerOptions => {
@@ -9028,6 +9054,10 @@ export const getEmitModuleResolutionKind = computedOptions.moduleResolution.comp
 /** @internal */
 export const getEmitModuleDetectionKind = computedOptions.moduleDetection.computeValue;
 /** @internal */
+export const getDefaultIsModuleExports = computedOptions.defaultIsModuleExports.computeValue;
+/** @internal */
+export const getAllowRequireESM = computedOptions.allowRequireESM.computeValue;
+/** @internal */
 export const getIsolatedModules = computedOptions.isolatedModules.computeValue;
 /** @internal */
 export const getESModuleInterop = computedOptions.esModuleInterop.computeValue;
diff --git a/src/testRunner/compilerRunner.ts b/src/testRunner/compilerRunner.ts
index 93bc55c1159fe..18c9eb679db96 100644
--- a/src/testRunner/compilerRunner.ts
+++ b/src/testRunner/compilerRunner.ts
@@ -129,8 +129,10 @@ class CompilerTest {
     private static varyBy: readonly string[] = [
         "allowArbitraryExtensions",
         "allowImportingTsExtensions",
+        "allowRequireESM",
         "allowSyntheticDefaultImports",
         "alwaysStrict",
+        "defaultIsModuleExports",
         "downlevelIteration",
         "experimentalDecorators",
         "emitDecoratorMetadata",
diff --git a/tests/baselines/reference/api/typescript.d.ts b/tests/baselines/reference/api/typescript.d.ts
index b1ac4827d4fd1..f266a29a4b305 100644
--- a/tests/baselines/reference/api/typescript.d.ts
+++ b/tests/baselines/reference/api/typescript.d.ts
@@ -6902,6 +6902,7 @@ declare namespace ts {
         allowImportingTsExtensions?: boolean;
         allowJs?: boolean;
         allowArbitraryExtensions?: boolean;
+        allowRequireESM?: AllowRequireESM;
         allowSyntheticDefaultImports?: boolean;
         allowUmdGlobalAccess?: boolean;
         allowUnreachableCode?: boolean;
@@ -6916,6 +6917,7 @@ declare namespace ts {
         declarationMap?: boolean;
         emitDeclarationOnly?: boolean;
         declarationDir?: string;
+        defaultIsModuleExports?: DefaultIsModuleExports;
         disableSizeLimit?: boolean;
         disableSourceOfProjectReferenceRedirect?: boolean;
         disableSolutionSearching?: boolean;
@@ -7044,6 +7046,17 @@ declare namespace ts {
         NodeNext = 199,
         Preserve = 200,
     }
+    enum DefaultIsModuleExports {
+        Auto = 1,
+        Node16 = 100,
+        NodeNext = 199,
+    }
+    enum AllowRequireESM {
+        Never = 0,
+        Always = 1,
+        Node16 = 100,
+        NodeNext = 199,
+    }
     enum JsxEmit {
         None = 0,
         Preserve = 1,
diff --git a/tests/baselines/reference/config/initTSConfig/Default initialized TSConfig/tsconfig.json b/tests/baselines/reference/config/initTSConfig/Default initialized TSConfig/tsconfig.json
index 8bb6097f80145..5f4490bb821c6 100644
--- a/tests/baselines/reference/config/initTSConfig/Default initialized TSConfig/tsconfig.json	
+++ b/tests/baselines/reference/config/initTSConfig/Default initialized TSConfig/tsconfig.json	
@@ -39,6 +39,8 @@
     // "resolvePackageJsonExports": true,                /* Use the package.json 'exports' field when resolving package imports. */
     // "resolvePackageJsonImports": true,                /* Use the package.json 'imports' field when resolving imports. */
     // "customConditions": [],                           /* Conditions to set in addition to the resolver-specific defaults when resolving imports. */
+    // "defaultIsModuleExports": "auto",                 /* Specify the target runtime's rules for default imports targeting CommonJS modules. */
+    // "allowRequireESM": "never",                       /* Specify the target runtime's rules for CommonJS 'require' calls targeting ECMAScript modules. */
     // "resolveJsonModule": true,                        /* Enable importing .json files. */
     // "allowArbitraryExtensions": true,                 /* Enable importing files with any extension, provided a declaration file is present. */
     // "noResolve": true,                                /* Disallow 'import's, 'require's or '<reference>'s from expanding the number of files TypeScript should add to a project. */
diff --git a/tests/baselines/reference/config/initTSConfig/Initialized TSConfig with --help/tsconfig.json b/tests/baselines/reference/config/initTSConfig/Initialized TSConfig with --help/tsconfig.json
index 8bb6097f80145..5f4490bb821c6 100644
--- a/tests/baselines/reference/config/initTSConfig/Initialized TSConfig with --help/tsconfig.json	
+++ b/tests/baselines/reference/config/initTSConfig/Initialized TSConfig with --help/tsconfig.json	
@@ -39,6 +39,8 @@
     // "resolvePackageJsonExports": true,                /* Use the package.json 'exports' field when resolving package imports. */
     // "resolvePackageJsonImports": true,                /* Use the package.json 'imports' field when resolving imports. */
     // "customConditions": [],                           /* Conditions to set in addition to the resolver-specific defaults when resolving imports. */
+    // "defaultIsModuleExports": "auto",                 /* Specify the target runtime's rules for default imports targeting CommonJS modules. */
+    // "allowRequireESM": "never",                       /* Specify the target runtime's rules for CommonJS 'require' calls targeting ECMAScript modules. */
     // "resolveJsonModule": true,                        /* Enable importing .json files. */
     // "allowArbitraryExtensions": true,                 /* Enable importing files with any extension, provided a declaration file is present. */
     // "noResolve": true,                                /* Disallow 'import's, 'require's or '<reference>'s from expanding the number of files TypeScript should add to a project. */
diff --git a/tests/baselines/reference/config/initTSConfig/Initialized TSConfig with --watch/tsconfig.json b/tests/baselines/reference/config/initTSConfig/Initialized TSConfig with --watch/tsconfig.json
index 8bb6097f80145..5f4490bb821c6 100644
--- a/tests/baselines/reference/config/initTSConfig/Initialized TSConfig with --watch/tsconfig.json	
+++ b/tests/baselines/reference/config/initTSConfig/Initialized TSConfig with --watch/tsconfig.json	
@@ -39,6 +39,8 @@
     // "resolvePackageJsonExports": true,                /* Use the package.json 'exports' field when resolving package imports. */
     // "resolvePackageJsonImports": true,                /* Use the package.json 'imports' field when resolving imports. */
     // "customConditions": [],                           /* Conditions to set in addition to the resolver-specific defaults when resolving imports. */
+    // "defaultIsModuleExports": "auto",                 /* Specify the target runtime's rules for default imports targeting CommonJS modules. */
+    // "allowRequireESM": "never",                       /* Specify the target runtime's rules for CommonJS 'require' calls targeting ECMAScript modules. */
     // "resolveJsonModule": true,                        /* Enable importing .json files. */
     // "allowArbitraryExtensions": true,                 /* Enable importing files with any extension, provided a declaration file is present. */
     // "noResolve": true,                                /* Disallow 'import's, 'require's or '<reference>'s from expanding the number of files TypeScript should add to a project. */
diff --git a/tests/baselines/reference/config/initTSConfig/Initialized TSConfig with advanced options/tsconfig.json b/tests/baselines/reference/config/initTSConfig/Initialized TSConfig with advanced options/tsconfig.json
index b3d05912583d9..a7081180b6039 100644
--- a/tests/baselines/reference/config/initTSConfig/Initialized TSConfig with advanced options/tsconfig.json	
+++ b/tests/baselines/reference/config/initTSConfig/Initialized TSConfig with advanced options/tsconfig.json	
@@ -39,6 +39,8 @@
     // "resolvePackageJsonExports": true,                /* Use the package.json 'exports' field when resolving package imports. */
     // "resolvePackageJsonImports": true,                /* Use the package.json 'imports' field when resolving imports. */
     // "customConditions": [],                           /* Conditions to set in addition to the resolver-specific defaults when resolving imports. */
+    // "defaultIsModuleExports": "auto",                 /* Specify the target runtime's rules for default imports targeting CommonJS modules. */
+    // "allowRequireESM": "never",                       /* Specify the target runtime's rules for CommonJS 'require' calls targeting ECMAScript modules. */
     // "resolveJsonModule": true,                        /* Enable importing .json files. */
     // "allowArbitraryExtensions": true,                 /* Enable importing files with any extension, provided a declaration file is present. */
     // "noResolve": true,                                /* Disallow 'import's, 'require's or '<reference>'s from expanding the number of files TypeScript should add to a project. */
diff --git a/tests/baselines/reference/config/initTSConfig/Initialized TSConfig with boolean value compiler options/tsconfig.json b/tests/baselines/reference/config/initTSConfig/Initialized TSConfig with boolean value compiler options/tsconfig.json
index 558f4243438d2..40e046ed10df5 100644
--- a/tests/baselines/reference/config/initTSConfig/Initialized TSConfig with boolean value compiler options/tsconfig.json	
+++ b/tests/baselines/reference/config/initTSConfig/Initialized TSConfig with boolean value compiler options/tsconfig.json	
@@ -39,6 +39,8 @@
     // "resolvePackageJsonExports": true,                /* Use the package.json 'exports' field when resolving package imports. */
     // "resolvePackageJsonImports": true,                /* Use the package.json 'imports' field when resolving imports. */
     // "customConditions": [],                           /* Conditions to set in addition to the resolver-specific defaults when resolving imports. */
+    // "defaultIsModuleExports": "auto",                 /* Specify the target runtime's rules for default imports targeting CommonJS modules. */
+    // "allowRequireESM": "never",                       /* Specify the target runtime's rules for CommonJS 'require' calls targeting ECMAScript modules. */
     // "resolveJsonModule": true,                        /* Enable importing .json files. */
     // "allowArbitraryExtensions": true,                 /* Enable importing files with any extension, provided a declaration file is present. */
     // "noResolve": true,                                /* Disallow 'import's, 'require's or '<reference>'s from expanding the number of files TypeScript should add to a project. */
diff --git a/tests/baselines/reference/config/initTSConfig/Initialized TSConfig with enum value compiler options/tsconfig.json b/tests/baselines/reference/config/initTSConfig/Initialized TSConfig with enum value compiler options/tsconfig.json
index 5679f8b921cdf..f87bb3feb24db 100644
--- a/tests/baselines/reference/config/initTSConfig/Initialized TSConfig with enum value compiler options/tsconfig.json	
+++ b/tests/baselines/reference/config/initTSConfig/Initialized TSConfig with enum value compiler options/tsconfig.json	
@@ -39,6 +39,8 @@
     // "resolvePackageJsonExports": true,                /* Use the package.json 'exports' field when resolving package imports. */
     // "resolvePackageJsonImports": true,                /* Use the package.json 'imports' field when resolving imports. */
     // "customConditions": [],                           /* Conditions to set in addition to the resolver-specific defaults when resolving imports. */
+    // "defaultIsModuleExports": "auto",                 /* Specify the target runtime's rules for default imports targeting CommonJS modules. */
+    // "allowRequireESM": "never",                       /* Specify the target runtime's rules for CommonJS 'require' calls targeting ECMAScript modules. */
     // "resolveJsonModule": true,                        /* Enable importing .json files. */
     // "allowArbitraryExtensions": true,                 /* Enable importing files with any extension, provided a declaration file is present. */
     // "noResolve": true,                                /* Disallow 'import's, 'require's or '<reference>'s from expanding the number of files TypeScript should add to a project. */
diff --git a/tests/baselines/reference/config/initTSConfig/Initialized TSConfig with files options/tsconfig.json b/tests/baselines/reference/config/initTSConfig/Initialized TSConfig with files options/tsconfig.json
index 535e6a2d97860..1bb17f3d0728d 100644
--- a/tests/baselines/reference/config/initTSConfig/Initialized TSConfig with files options/tsconfig.json	
+++ b/tests/baselines/reference/config/initTSConfig/Initialized TSConfig with files options/tsconfig.json	
@@ -39,6 +39,8 @@
     // "resolvePackageJsonExports": true,                /* Use the package.json 'exports' field when resolving package imports. */
     // "resolvePackageJsonImports": true,                /* Use the package.json 'imports' field when resolving imports. */
     // "customConditions": [],                           /* Conditions to set in addition to the resolver-specific defaults when resolving imports. */
+    // "defaultIsModuleExports": "auto",                 /* Specify the target runtime's rules for default imports targeting CommonJS modules. */
+    // "allowRequireESM": "never",                       /* Specify the target runtime's rules for CommonJS 'require' calls targeting ECMAScript modules. */
     // "resolveJsonModule": true,                        /* Enable importing .json files. */
     // "allowArbitraryExtensions": true,                 /* Enable importing files with any extension, provided a declaration file is present. */
     // "noResolve": true,                                /* Disallow 'import's, 'require's or '<reference>'s from expanding the number of files TypeScript should add to a project. */
diff --git a/tests/baselines/reference/config/initTSConfig/Initialized TSConfig with incorrect compiler option value/tsconfig.json b/tests/baselines/reference/config/initTSConfig/Initialized TSConfig with incorrect compiler option value/tsconfig.json
index da587b6bded7f..4a3e4fa8a8b14 100644
--- a/tests/baselines/reference/config/initTSConfig/Initialized TSConfig with incorrect compiler option value/tsconfig.json	
+++ b/tests/baselines/reference/config/initTSConfig/Initialized TSConfig with incorrect compiler option value/tsconfig.json	
@@ -39,6 +39,8 @@
     // "resolvePackageJsonExports": true,                /* Use the package.json 'exports' field when resolving package imports. */
     // "resolvePackageJsonImports": true,                /* Use the package.json 'imports' field when resolving imports. */
     // "customConditions": [],                           /* Conditions to set in addition to the resolver-specific defaults when resolving imports. */
+    // "defaultIsModuleExports": "auto",                 /* Specify the target runtime's rules for default imports targeting CommonJS modules. */
+    // "allowRequireESM": "never",                       /* Specify the target runtime's rules for CommonJS 'require' calls targeting ECMAScript modules. */
     // "resolveJsonModule": true,                        /* Enable importing .json files. */
     // "allowArbitraryExtensions": true,                 /* Enable importing files with any extension, provided a declaration file is present. */
     // "noResolve": true,                                /* Disallow 'import's, 'require's or '<reference>'s from expanding the number of files TypeScript should add to a project. */
diff --git a/tests/baselines/reference/config/initTSConfig/Initialized TSConfig with incorrect compiler option/tsconfig.json b/tests/baselines/reference/config/initTSConfig/Initialized TSConfig with incorrect compiler option/tsconfig.json
index 8bb6097f80145..5f4490bb821c6 100644
--- a/tests/baselines/reference/config/initTSConfig/Initialized TSConfig with incorrect compiler option/tsconfig.json	
+++ b/tests/baselines/reference/config/initTSConfig/Initialized TSConfig with incorrect compiler option/tsconfig.json	
@@ -39,6 +39,8 @@
     // "resolvePackageJsonExports": true,                /* Use the package.json 'exports' field when resolving package imports. */
     // "resolvePackageJsonImports": true,                /* Use the package.json 'imports' field when resolving imports. */
     // "customConditions": [],                           /* Conditions to set in addition to the resolver-specific defaults when resolving imports. */
+    // "defaultIsModuleExports": "auto",                 /* Specify the target runtime's rules for default imports targeting CommonJS modules. */
+    // "allowRequireESM": "never",                       /* Specify the target runtime's rules for CommonJS 'require' calls targeting ECMAScript modules. */
     // "resolveJsonModule": true,                        /* Enable importing .json files. */
     // "allowArbitraryExtensions": true,                 /* Enable importing files with any extension, provided a declaration file is present. */
     // "noResolve": true,                                /* Disallow 'import's, 'require's or '<reference>'s from expanding the number of files TypeScript should add to a project. */
diff --git a/tests/baselines/reference/config/initTSConfig/Initialized TSConfig with list compiler options with enum value/tsconfig.json b/tests/baselines/reference/config/initTSConfig/Initialized TSConfig with list compiler options with enum value/tsconfig.json
index a6e74d92a6a8f..302fe7dd4b7df 100644
--- a/tests/baselines/reference/config/initTSConfig/Initialized TSConfig with list compiler options with enum value/tsconfig.json	
+++ b/tests/baselines/reference/config/initTSConfig/Initialized TSConfig with list compiler options with enum value/tsconfig.json	
@@ -39,6 +39,8 @@
     // "resolvePackageJsonExports": true,                /* Use the package.json 'exports' field when resolving package imports. */
     // "resolvePackageJsonImports": true,                /* Use the package.json 'imports' field when resolving imports. */
     // "customConditions": [],                           /* Conditions to set in addition to the resolver-specific defaults when resolving imports. */
+    // "defaultIsModuleExports": "auto",                 /* Specify the target runtime's rules for default imports targeting CommonJS modules. */
+    // "allowRequireESM": "never",                       /* Specify the target runtime's rules for CommonJS 'require' calls targeting ECMAScript modules. */
     // "resolveJsonModule": true,                        /* Enable importing .json files. */
     // "allowArbitraryExtensions": true,                 /* Enable importing files with any extension, provided a declaration file is present. */
     // "noResolve": true,                                /* Disallow 'import's, 'require's or '<reference>'s from expanding the number of files TypeScript should add to a project. */
diff --git a/tests/baselines/reference/config/initTSConfig/Initialized TSConfig with list compiler options/tsconfig.json b/tests/baselines/reference/config/initTSConfig/Initialized TSConfig with list compiler options/tsconfig.json
index 41c2964e0e7fa..9f582764d85d1 100644
--- a/tests/baselines/reference/config/initTSConfig/Initialized TSConfig with list compiler options/tsconfig.json	
+++ b/tests/baselines/reference/config/initTSConfig/Initialized TSConfig with list compiler options/tsconfig.json	
@@ -39,6 +39,8 @@
     // "resolvePackageJsonExports": true,                /* Use the package.json 'exports' field when resolving package imports. */
     // "resolvePackageJsonImports": true,                /* Use the package.json 'imports' field when resolving imports. */
     // "customConditions": [],                           /* Conditions to set in addition to the resolver-specific defaults when resolving imports. */
+    // "defaultIsModuleExports": "auto",                 /* Specify the target runtime's rules for default imports targeting CommonJS modules. */
+    // "allowRequireESM": "never",                       /* Specify the target runtime's rules for CommonJS 'require' calls targeting ECMAScript modules. */
     // "resolveJsonModule": true,                        /* Enable importing .json files. */
     // "allowArbitraryExtensions": true,                 /* Enable importing files with any extension, provided a declaration file is present. */
     // "noResolve": true,                                /* Disallow 'import's, 'require's or '<reference>'s from expanding the number of files TypeScript should add to a project. */
diff --git a/tests/baselines/reference/config/showConfig/Shows tsconfig for single option/allowRequireESM/tsconfig.json b/tests/baselines/reference/config/showConfig/Shows tsconfig for single option/allowRequireESM/tsconfig.json
new file mode 100644
index 0000000000000..47369742b654f
--- /dev/null
+++ b/tests/baselines/reference/config/showConfig/Shows tsconfig for single option/allowRequireESM/tsconfig.json	
@@ -0,0 +1,5 @@
+{
+    "compilerOptions": {
+        "allowRequireESM": "never"
+    }
+}
diff --git a/tests/baselines/reference/config/showConfig/Shows tsconfig for single option/defaultIsModuleExports/tsconfig.json b/tests/baselines/reference/config/showConfig/Shows tsconfig for single option/defaultIsModuleExports/tsconfig.json
new file mode 100644
index 0000000000000..313c3e7950b09
--- /dev/null
+++ b/tests/baselines/reference/config/showConfig/Shows tsconfig for single option/defaultIsModuleExports/tsconfig.json	
@@ -0,0 +1,5 @@
+{
+    "compilerOptions": {
+        "defaultIsModuleExports": "auto"
+    }
+}
diff --git a/tests/baselines/reference/esbuildInterop(defaultismoduleexports=auto).errors.txt b/tests/baselines/reference/esbuildInterop(defaultismoduleexports=auto).errors.txt
new file mode 100644
index 0000000000000..b5bc74655743c
--- /dev/null
+++ b/tests/baselines/reference/esbuildInterop(defaultismoduleexports=auto).errors.txt
@@ -0,0 +1,26 @@
+/index.ts(3,5): error TS2339: Property 'default' does not exist on type 'string'.
+
+
+==== /node_modules/dep/package.json (0 errors) ====
+    {
+        "name": "dep",
+        "version": "1.0.0",
+        "main": "index.js"
+    }
+    
+==== /node_modules/dep/index.d.ts (0 errors) ====
+    declare const _default: string;
+    export default _default;
+    
+==== /package.json (0 errors) ====
+    {
+      "type": "module"
+    }
+    
+==== /index.ts (1 errors) ====
+    import dep from "dep";
+    dep.toLowerCase(); // Error in nodenext
+    dep.default.toLowerCase(); // Error in auto
+        ~~~~~~~
+!!! error TS2339: Property 'default' does not exist on type 'string'.
+    
\ No newline at end of file
diff --git a/tests/baselines/reference/esbuildInterop(defaultismoduleexports=nodenext).errors.txt b/tests/baselines/reference/esbuildInterop(defaultismoduleexports=nodenext).errors.txt
new file mode 100644
index 0000000000000..ee0d91b41e490
--- /dev/null
+++ b/tests/baselines/reference/esbuildInterop(defaultismoduleexports=nodenext).errors.txt
@@ -0,0 +1,26 @@
+/index.ts(2,5): error TS2339: Property 'toLowerCase' does not exist on type 'typeof import("/node_modules/dep/index")'.
+
+
+==== /node_modules/dep/package.json (0 errors) ====
+    {
+        "name": "dep",
+        "version": "1.0.0",
+        "main": "index.js"
+    }
+    
+==== /node_modules/dep/index.d.ts (0 errors) ====
+    declare const _default: string;
+    export default _default;
+    
+==== /package.json (0 errors) ====
+    {
+      "type": "module"
+    }
+    
+==== /index.ts (1 errors) ====
+    import dep from "dep";
+    dep.toLowerCase(); // Error in nodenext
+        ~~~~~~~~~~~
+!!! error TS2339: Property 'toLowerCase' does not exist on type 'typeof import("/node_modules/dep/index")'.
+    dep.default.toLowerCase(); // Error in auto
+    
\ No newline at end of file
diff --git a/tests/baselines/reference/webpackInterop(allowrequireesm=node16).errors.txt b/tests/baselines/reference/webpackInterop(allowrequireesm=node16).errors.txt
new file mode 100644
index 0000000000000..70e55cc2d3bbf
--- /dev/null
+++ b/tests/baselines/reference/webpackInterop(allowrequireesm=node16).errors.txt
@@ -0,0 +1,21 @@
+/main2.js(2,20): error TS1479: The current file is a CommonJS module whose imports will produce 'require' calls; however, the referenced file is an ECMAScript module and cannot be imported with 'require'. Consider writing a dynamic 'import("./marked-esm.mjs")' call instead.
+  To convert this file to an ECMAScript module, change its file extension to '.mjs' or create a local package.json file with `{ "type": "module" }`.
+
+
+==== /main2.js (1 errors) ====
+    const _1 = require("./unmarked-esm.js");
+    const _2 = require("./marked-esm.mjs");
+                       ~~~~~~~~~~~~~~~~~~
+!!! error TS1479: The current file is a CommonJS module whose imports will produce 'require' calls; however, the referenced file is an ECMAScript module and cannot be imported with 'require'. Consider writing a dynamic 'import("./marked-esm.mjs")' call instead.
+!!! error TS1479:   To convert this file to an ECMAScript module, change its file extension to '.mjs' or create a local package.json file with `{ "type": "module" }`.
+    
+==== /unmarked-esm.js (0 errors) ====
+    export default "unmarked-esm";
+    
+==== /marked-esm.mjs (0 errors) ====
+    export default "marked-esm";
+    
+==== /main1.js (0 errors) ====
+    import unmarked from "./unmarked-esm.js";
+    import marked from "./marked-esm.mjs";
+    
\ No newline at end of file
diff --git a/tests/cases/conformance/module/esbuildInterop.ts b/tests/cases/conformance/module/esbuildInterop.ts
new file mode 100644
index 0000000000000..5b31ff4f6759e
--- /dev/null
+++ b/tests/cases/conformance/module/esbuildInterop.ts
@@ -0,0 +1,26 @@
+// @module: esnext
+// @moduleResolution: bundler
+// @defaultIsModuleExports: auto, nodenext
+// @noEmit: true
+// @noTypesAndSymbols: true
+
+// @Filename: /node_modules/dep/package.json
+{
+    "name": "dep",
+    "version": "1.0.0",
+    "main": "index.js"
+}
+
+// @Filename: /node_modules/dep/index.d.ts
+declare const _default: string;
+export default _default;
+
+// @Filename: /package.json
+{
+  "type": "module"
+}
+
+// @Filename: /index.ts
+import dep from "dep";
+dep.toLowerCase(); // Error in nodenext
+dep.default.toLowerCase(); // Error in auto
diff --git a/tests/cases/conformance/module/webpackInterop.ts b/tests/cases/conformance/module/webpackInterop.ts
new file mode 100644
index 0000000000000..c05df67abc901
--- /dev/null
+++ b/tests/cases/conformance/module/webpackInterop.ts
@@ -0,0 +1,21 @@
+// @module: preserve
+// @moduleResolution: bundler
+// @defaultIsModuleExports: node16
+// @allowRequireESM: always, node16
+// @noEmit: true
+// @checkJs: true
+// @noTypesAndSymbols: true
+
+// @Filename: /unmarked-esm.js
+export default "unmarked-esm";
+
+// @Filename: /marked-esm.mjs
+export default "marked-esm";
+
+// @Filename: /main1.js
+import unmarked from "./unmarked-esm.js";
+import marked from "./marked-esm.mjs";
+
+// @Filename: /main2.js
+const _1 = require("./unmarked-esm.js");
+const _2 = require("./marked-esm.mjs");