diff --git a/src/compiler/checker.ts b/src/compiler/checker.ts
index 47288fdde3259..07e2f1d573711 100644
--- a/src/compiler/checker.ts
+++ b/src/compiler/checker.ts
@@ -814,6 +814,7 @@ import {
     nodeIsPresent,
     nodeIsSynthesized,
     NodeLinks,
+    nodeModulesPathPart,
     nodeStartsNewLexicalEnvironment,
     NodeWithTypeArguments,
     NonNullChain,
@@ -4765,7 +4766,7 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
 
             if (sourceFile.symbol) {
                 if (resolvedModule.isExternalLibraryImport && !resolutionExtensionIsTSOrJson(resolvedModule.extension)) {
-                    errorOnImplicitAnyModule(/*isError*/ false, errorNode, resolvedModule, moduleReference);
+                    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);
@@ -4853,7 +4854,7 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
                 error(errorNode, diag, moduleReference, resolvedModule!.resolvedFileName);
             }
             else {
-                errorOnImplicitAnyModule(/*isError*/ noImplicitAny && !!moduleNotFoundError, errorNode, resolvedModule!, moduleReference);
+                errorOnImplicitAnyModule(/*isError*/ noImplicitAny && !!moduleNotFoundError, errorNode, currentSourceFile, mode, resolvedModule!, moduleReference);
             }
             // Failed imports and untyped modules are both treated in an untyped manner; only difference is whether we give a diagnostic first.
             return undefined;
@@ -4923,25 +4924,33 @@ export function createTypeChecker(host: TypeCheckerHost): TypeChecker {
         }
     }
 
-    function errorOnImplicitAnyModule(isError: boolean, errorNode: Node, { packageId, resolvedFileName }: ResolvedModuleFull, moduleReference: string): void {
-        const errorInfo = !isExternalModuleNameRelative(moduleReference) && packageId
-            ? typesPackageExists(packageId.name)
+    function errorOnImplicitAnyModule(isError: boolean, errorNode: Node, sourceFile: SourceFile, mode: ResolutionMode, { packageId, resolvedFileName }: ResolvedModuleFull, moduleReference: string): void {
+        let errorInfo;
+        if (!isExternalModuleNameRelative(moduleReference) && packageId) {
+            const legacyResult = sourceFile.resolvedModules?.get(moduleReference, mode)?.legacyResult;
+            errorInfo = legacyResult
                 ? chainDiagnosticMessages(
                     /*details*/ undefined,
-                    Diagnostics.If_the_0_package_actually_exposes_this_module_consider_sending_a_pull_request_to_amend_https_Colon_Slash_Slashgithub_com_SlashDefinitelyTyped_SlashDefinitelyTyped_Slashtree_Slashmaster_Slashtypes_Slash_1,
-                    packageId.name, mangleScopedPackageName(packageId.name))
-                : packageBundlesTypes(packageId.name)
+                    Diagnostics.There_are_types_at_0_but_this_result_could_not_be_resolved_when_respecting_package_json_exports_The_1_library_may_need_to_update_its_package_json,
+                    legacyResult,
+                    legacyResult.indexOf(nodeModulesPathPart + "@types/") > -1 ? `@types/${mangleScopedPackageName(packageId.name)}` : packageId.name)
+                : typesPackageExists(packageId.name)
                     ? chainDiagnosticMessages(
                         /*details*/ undefined,
-                        Diagnostics.If_the_0_package_actually_exposes_this_module_try_adding_a_new_declaration_d_ts_file_containing_declare_module_1,
-                        packageId.name,
-                        moduleReference)
-                    : chainDiagnosticMessages(
-                        /*details*/ undefined,
-                        Diagnostics.Try_npm_i_save_dev_types_Slash_1_if_it_exists_or_add_a_new_declaration_d_ts_file_containing_declare_module_0,
-                        moduleReference,
-                        mangleScopedPackageName(packageId.name))
-            : undefined;
+                        Diagnostics.If_the_0_package_actually_exposes_this_module_consider_sending_a_pull_request_to_amend_https_Colon_Slash_Slashgithub_com_SlashDefinitelyTyped_SlashDefinitelyTyped_Slashtree_Slashmaster_Slashtypes_Slash_1,
+                        packageId.name, mangleScopedPackageName(packageId.name))
+                    : packageBundlesTypes(packageId.name)
+                        ? chainDiagnosticMessages(
+                            /*details*/ undefined,
+                            Diagnostics.If_the_0_package_actually_exposes_this_module_try_adding_a_new_declaration_d_ts_file_containing_declare_module_1,
+                            packageId.name,
+                            moduleReference)
+                        : chainDiagnosticMessages(
+                            /*details*/ undefined,
+                            Diagnostics.Try_npm_i_save_dev_types_Slash_1_if_it_exists_or_add_a_new_declaration_d_ts_file_containing_declare_module_0,
+                            moduleReference,
+                            mangleScopedPackageName(packageId.name));
+        }
         errorOrSuggestion(isError, errorNode, chainDiagnosticMessages(
             errorInfo,
             Diagnostics.Could_not_find_a_declaration_file_for_module_0_1_implicitly_has_an_any_type,
diff --git a/src/compiler/commandLineParser.ts b/src/compiler/commandLineParser.ts
index 1010bd171c63a..7e3f7b80f0f5f 100644
--- a/src/compiler/commandLineParser.ts
+++ b/src/compiler/commandLineParser.ts
@@ -964,7 +964,7 @@ const commandOptionsWithoutBuild: CommandLineOption[] = [
         type: new Map(Object.entries({
             // N.B. The first entry specifies the value shown in `tsc --init`
             node10: ModuleResolutionKind.Node10,
-            node: ModuleResolutionKind.Node10,
+            node: ModuleResolutionKind.Bundler,
             classic: ModuleResolutionKind.Classic,
             node16: ModuleResolutionKind.Node16,
             nodenext: ModuleResolutionKind.NodeNext,
diff --git a/src/compiler/diagnosticMessages.json b/src/compiler/diagnosticMessages.json
index 7573cbc29eaf3..85adb10def96b 100644
--- a/src/compiler/diagnosticMessages.json
+++ b/src/compiler/diagnosticMessages.json
@@ -5219,6 +5219,14 @@
         "category": "Message",
         "code": 6276
     },
+    "Resolution of non-relative name failed; trying with modern Node resolution features disabled to see if npm library needs configuration update.": {
+        "category": "Message",
+        "code": 6277
+    },
+    "There are types at '{0}', but this result could not be resolved when respecting package.json \"exports\". The '{1}' library may need to update its package.json.": {
+        "category": "Message",
+        "code": 6278
+    },
 
     "Enable project compilation": {
         "category": "Message",
diff --git a/src/compiler/moduleNameResolver.ts b/src/compiler/moduleNameResolver.ts
index be8573b075db3..0125fa3503ce8 100644
--- a/src/compiler/moduleNameResolver.ts
+++ b/src/compiler/moduleNameResolver.ts
@@ -214,7 +214,8 @@ function createResolvedModuleWithFailedLookupLocations(
     failedLookupLocations: string[],
     affectingLocations: string[],
     diagnostics: Diagnostic[],
-    resultFromCache: ResolvedModuleWithFailedLookupLocations | undefined
+    resultFromCache: ResolvedModuleWithFailedLookupLocations | undefined,
+    legacyResult?: string,
 ): ResolvedModuleWithFailedLookupLocations {
     if (resultFromCache) {
         resultFromCache.failedLookupLocations = updateResolutionField(resultFromCache.failedLookupLocations, failedLookupLocations);
@@ -234,6 +235,7 @@ function createResolvedModuleWithFailedLookupLocations(
         failedLookupLocations: initializeResolutionField(failedLookupLocations),
         affectingLocations: initializeResolutionField(affectingLocations),
         resolutionDiagnostics: initializeResolutionField(diagnostics),
+        legacyResult,
     };
 }
 function initializeResolutionField<T>(value: T[]): T[] | undefined {
@@ -1665,12 +1667,37 @@ function nodeModuleNameResolverWorker(features: NodeResolutionFeatures, moduleNa
         const priorityExtensions = extensions & (Extensions.TypeScript | Extensions.Declaration);
         const secondaryExtensions = extensions & ~(Extensions.TypeScript | Extensions.Declaration);
         result =
-            priorityExtensions && tryResolve(priorityExtensions) ||
-            secondaryExtensions && tryResolve(secondaryExtensions) ||
+            priorityExtensions && tryResolve(priorityExtensions, state) ||
+            secondaryExtensions && tryResolve(secondaryExtensions, state) ||
             undefined;
     }
     else {
-        result = tryResolve(extensions);
+        result = tryResolve(extensions, state);
+    }
+
+    // For non-relative names that resolved to JS but no types in modes that look up an "import" condition in package.json "exports",
+    // try again with "exports" disabled to try to detect if this is likely a configuration error in a dependency's package.json.
+    let legacyResult;
+    if (result?.value?.isExternalLibraryImport
+        && !isConfigLookup
+        && extensions & (Extensions.TypeScript | Extensions.Declaration)
+        && features & NodeResolutionFeatures.Exports
+        && !isExternalModuleNameRelative(moduleName)
+        && !extensionIsOk(Extensions.TypeScript | Extensions.Declaration, result.value.resolved.extension)
+        && conditions.indexOf("import") > -1
+    ) {
+        traceIfEnabled(state, Diagnostics.Resolution_of_non_relative_name_failed_trying_with_modern_Node_resolution_features_disabled_to_see_if_npm_library_needs_configuration_update);
+        const diagnosticState = {
+            ...state,
+            features: state.features & ~NodeResolutionFeatures.Exports,
+            failedLookupLocations: [],
+            affectingLocations: [],
+            reportDiagnostic: noop,
+        };
+        const diagnosticResult = tryResolve(extensions & (Extensions.TypeScript | Extensions.Declaration), diagnosticState);
+        if (diagnosticResult?.value?.isExternalLibraryImport) {
+            legacyResult = diagnosticResult.value.resolved.path;
+        }
     }
 
     return createResolvedModuleWithFailedLookupLocations(
@@ -1679,10 +1706,11 @@ function nodeModuleNameResolverWorker(features: NodeResolutionFeatures, moduleNa
         failedLookupLocations,
         affectingLocations,
         diagnostics,
-        state.resultFromCache
+        state.resultFromCache,
+        legacyResult,
     );
 
-    function tryResolve(extensions: Extensions): SearchResult<{ resolved: Resolved, isExternalLibraryImport: boolean }> {
+    function tryResolve(extensions: Extensions, state: ModuleResolutionState): SearchResult<{ resolved: Resolved, isExternalLibraryImport: boolean }> {
         const loader: ResolutionKindSpecificLoader = (extensions, candidate, onlyRecordFailures, state) => nodeLoadModuleByRelativeName(extensions, candidate, onlyRecordFailures, state, /*considerPackageJson*/ true);
         const resolved = tryLoadModuleUsingOptionalResolutionSettings(extensions, moduleName, containingDirectory, loader, state);
         if (resolved) {
@@ -2756,27 +2784,31 @@ function loadModuleFromImmediateNodeModulesDirectory(extensions: Extensions, mod
 
 function loadModuleFromSpecificNodeModulesDirectory(extensions: Extensions, moduleName: string, nodeModulesDirectory: string, nodeModulesDirectoryExists: boolean, state: ModuleResolutionState, cache: ModuleResolutionCache | undefined, redirectedReference: ResolvedProjectReference | undefined): Resolved | undefined {
     const candidate = normalizePath(combinePaths(nodeModulesDirectory, moduleName));
+    const { packageName, rest } = parsePackageName(moduleName);
+    const packageDirectory = combinePaths(nodeModulesDirectory, packageName);
 
+    let rootPackageInfo: PackageJsonInfo | undefined;
     // First look for a nested package.json, as in `node_modules/foo/bar/package.json`.
     let packageInfo = getPackageJsonInfo(candidate, !nodeModulesDirectoryExists, state);
     // But only if we're not respecting export maps (if we are, we might redirect around this location)
-    if (!(state.features & NodeResolutionFeatures.Exports)) {
-        if (packageInfo) {
-            const fromFile = loadModuleFromFile(extensions, candidate, !nodeModulesDirectoryExists, state);
-            if (fromFile) {
-                return noPackageId(fromFile);
-            }
-
-            const fromDirectory = loadNodeModuleFromDirectoryWorker(
-                extensions,
-                candidate,
-                !nodeModulesDirectoryExists,
-                state,
-                packageInfo.contents.packageJsonContent,
-                getVersionPathsOfPackageJsonInfo(packageInfo, state),
-            );
-            return withPackageId(packageInfo, fromDirectory);
+    if (rest !== "" && packageInfo && (
+        !(state.features & NodeResolutionFeatures.Exports) ||
+        !hasProperty((rootPackageInfo = getPackageJsonInfo(packageDirectory, !nodeModulesDirectoryExists, state))?.contents.packageJsonContent ?? emptyArray, "exports")
+    )) {
+        const fromFile = loadModuleFromFile(extensions, candidate, !nodeModulesDirectoryExists, state);
+        if (fromFile) {
+            return noPackageId(fromFile);
         }
+
+        const fromDirectory = loadNodeModuleFromDirectoryWorker(
+            extensions,
+            candidate,
+            !nodeModulesDirectoryExists,
+            state,
+            packageInfo.contents.packageJsonContent,
+            getVersionPathsOfPackageJsonInfo(packageInfo, state),
+        );
+        return withPackageId(packageInfo, fromDirectory);
     }
 
     const loader: ResolutionKindSpecificLoader = (extensions, candidate, onlyRecordFailures, state) => {
@@ -2803,11 +2835,9 @@ function loadModuleFromSpecificNodeModulesDirectory(extensions: Extensions, modu
         return withPackageId(packageInfo, pathAndExtension);
     };
 
-    const { packageName, rest } = parsePackageName(moduleName);
-    const packageDirectory = combinePaths(nodeModulesDirectory, packageName);
     if (rest !== "") {
         // Previous `packageInfo` may have been from a nested package.json; ensure we have the one from the package root now.
-        packageInfo = getPackageJsonInfo(packageDirectory, !nodeModulesDirectoryExists, state);
+        packageInfo = rootPackageInfo ?? getPackageJsonInfo(packageDirectory, !nodeModulesDirectoryExists, state);
     }
     // package exports are higher priority than file/directory/typesVersions lookups and (and, if there's exports present, blocks them)
     if (packageInfo && packageInfo.contents.packageJsonContent.exports && state.features & NodeResolutionFeatures.Exports) {
diff --git a/src/compiler/types.ts b/src/compiler/types.ts
index 44a716a516f7a..2663d678c3d50 100644
--- a/src/compiler/types.ts
+++ b/src/compiler/types.ts
@@ -7605,6 +7605,8 @@ export interface ResolvedModuleWithFailedLookupLocations {
     affectingLocations?: string[];
     /** @internal */
     resolutionDiagnostics?: Diagnostic[]
+    /** @internal */
+    legacyResult?: string;
 }
 
 export interface ResolvedTypeReferenceDirective {
diff --git a/tests/baselines/reference/nestedPackageJsonRedirect(moduleresolution=bundler).trace.json b/tests/baselines/reference/nestedPackageJsonRedirect(moduleresolution=bundler).trace.json
new file mode 100644
index 0000000000000..b6dd002185a28
--- /dev/null
+++ b/tests/baselines/reference/nestedPackageJsonRedirect(moduleresolution=bundler).trace.json
@@ -0,0 +1,17 @@
+[
+    "======== Resolving module '@restart/hooks/useMergedRefs' from '/main.ts'. ========",
+    "Explicitly specified module resolution kind: 'Bundler'.",
+    "File '/package.json' does not exist.",
+    "Loading module '@restart/hooks/useMergedRefs' from 'node_modules' folder, target file types: TypeScript, JavaScript, Declaration, JSON.",
+    "Found 'package.json' at '/node_modules/@restart/hooks/useMergedRefs/package.json'.",
+    "Found 'package.json' at '/node_modules/@restart/hooks/package.json'.",
+    "File '/node_modules/@restart/hooks/useMergedRefs.ts' does not exist.",
+    "File '/node_modules/@restart/hooks/useMergedRefs.tsx' does not exist.",
+    "File '/node_modules/@restart/hooks/useMergedRefs.d.ts' does not exist.",
+    "'package.json' does not have a 'typesVersions' field.",
+    "'package.json' does not have a 'typings' field.",
+    "'package.json' has 'types' field '../esm/useMergedRefs.d.ts' that references '/node_modules/@restart/hooks/esm/useMergedRefs.d.ts'.",
+    "File '/node_modules/@restart/hooks/esm/useMergedRefs.d.ts' exist - use it as a name resolution result.",
+    "Resolving real path for '/node_modules/@restart/hooks/esm/useMergedRefs.d.ts', result '/node_modules/@restart/hooks/esm/useMergedRefs.d.ts'.",
+    "======== Module name '@restart/hooks/useMergedRefs' was successfully resolved to '/node_modules/@restart/hooks/esm/useMergedRefs.d.ts'. ========"
+]
\ No newline at end of file
diff --git a/tests/baselines/reference/nestedPackageJsonRedirect(moduleresolution=node16).trace.json b/tests/baselines/reference/nestedPackageJsonRedirect(moduleresolution=node16).trace.json
new file mode 100644
index 0000000000000..4d8ad876095fe
--- /dev/null
+++ b/tests/baselines/reference/nestedPackageJsonRedirect(moduleresolution=node16).trace.json
@@ -0,0 +1,31 @@
+[
+    "File '/node_modules/@restart/hooks/esm/package.json' does not exist.",
+    "Found 'package.json' at '/node_modules/@restart/hooks/package.json'.",
+    "File '/package.json' does not exist.",
+    "======== Resolving module '@restart/hooks/useMergedRefs' from '/main.ts'. ========",
+    "Explicitly specified module resolution kind: 'Node16'.",
+    "Resolving in CJS mode with conditions 'node', 'require', 'types'.",
+    "File '/package.json' does not exist according to earlier cached lookups.",
+    "Loading module '@restart/hooks/useMergedRefs' from 'node_modules' folder, target file types: TypeScript, JavaScript, Declaration.",
+    "Found 'package.json' at '/node_modules/@restart/hooks/useMergedRefs/package.json'.",
+    "File '/node_modules/@restart/hooks/package.json' exists according to earlier cached lookups.",
+    "File '/node_modules/@restart/hooks/useMergedRefs.ts' does not exist.",
+    "File '/node_modules/@restart/hooks/useMergedRefs.tsx' does not exist.",
+    "File '/node_modules/@restart/hooks/useMergedRefs.d.ts' does not exist.",
+    "'package.json' does not have a 'typesVersions' field.",
+    "'package.json' does not have a 'typings' field.",
+    "'package.json' has 'types' field '../esm/useMergedRefs.d.ts' that references '/node_modules/@restart/hooks/esm/useMergedRefs.d.ts'.",
+    "File '/node_modules/@restart/hooks/esm/useMergedRefs.d.ts' exist - use it as a name resolution result.",
+    "Resolving real path for '/node_modules/@restart/hooks/esm/useMergedRefs.d.ts', result '/node_modules/@restart/hooks/esm/useMergedRefs.d.ts'.",
+    "======== Module name '@restart/hooks/useMergedRefs' was successfully resolved to '/node_modules/@restart/hooks/esm/useMergedRefs.d.ts'. ========",
+    "File 'package.json' does not exist.",
+    "File '/package.json' does not exist according to earlier cached lookups.",
+    "File 'package.json' does not exist according to earlier cached lookups.",
+    "File '/package.json' does not exist according to earlier cached lookups.",
+    "File 'package.json' does not exist according to earlier cached lookups.",
+    "File '/package.json' does not exist according to earlier cached lookups.",
+    "File 'package.json' does not exist according to earlier cached lookups.",
+    "File '/package.json' does not exist according to earlier cached lookups.",
+    "File 'package.json' does not exist according to earlier cached lookups.",
+    "File '/package.json' does not exist according to earlier cached lookups."
+]
\ No newline at end of file
diff --git a/tests/baselines/reference/nestedPackageJsonRedirect(moduleresolution=nodenext).trace.json b/tests/baselines/reference/nestedPackageJsonRedirect(moduleresolution=nodenext).trace.json
new file mode 100644
index 0000000000000..77e7411b6622e
--- /dev/null
+++ b/tests/baselines/reference/nestedPackageJsonRedirect(moduleresolution=nodenext).trace.json
@@ -0,0 +1,31 @@
+[
+    "File '/node_modules/@restart/hooks/esm/package.json' does not exist.",
+    "Found 'package.json' at '/node_modules/@restart/hooks/package.json'.",
+    "File '/package.json' does not exist.",
+    "======== Resolving module '@restart/hooks/useMergedRefs' from '/main.ts'. ========",
+    "Explicitly specified module resolution kind: 'NodeNext'.",
+    "Resolving in CJS mode with conditions 'node', 'require', 'types'.",
+    "File '/package.json' does not exist according to earlier cached lookups.",
+    "Loading module '@restart/hooks/useMergedRefs' from 'node_modules' folder, target file types: TypeScript, JavaScript, Declaration.",
+    "Found 'package.json' at '/node_modules/@restart/hooks/useMergedRefs/package.json'.",
+    "File '/node_modules/@restart/hooks/package.json' exists according to earlier cached lookups.",
+    "File '/node_modules/@restart/hooks/useMergedRefs.ts' does not exist.",
+    "File '/node_modules/@restart/hooks/useMergedRefs.tsx' does not exist.",
+    "File '/node_modules/@restart/hooks/useMergedRefs.d.ts' does not exist.",
+    "'package.json' does not have a 'typesVersions' field.",
+    "'package.json' does not have a 'typings' field.",
+    "'package.json' has 'types' field '../esm/useMergedRefs.d.ts' that references '/node_modules/@restart/hooks/esm/useMergedRefs.d.ts'.",
+    "File '/node_modules/@restart/hooks/esm/useMergedRefs.d.ts' exist - use it as a name resolution result.",
+    "Resolving real path for '/node_modules/@restart/hooks/esm/useMergedRefs.d.ts', result '/node_modules/@restart/hooks/esm/useMergedRefs.d.ts'.",
+    "======== Module name '@restart/hooks/useMergedRefs' was successfully resolved to '/node_modules/@restart/hooks/esm/useMergedRefs.d.ts'. ========",
+    "File 'package.json' does not exist.",
+    "File '/package.json' does not exist according to earlier cached lookups.",
+    "File 'package.json' does not exist according to earlier cached lookups.",
+    "File '/package.json' does not exist according to earlier cached lookups.",
+    "File 'package.json' does not exist according to earlier cached lookups.",
+    "File '/package.json' does not exist according to earlier cached lookups.",
+    "File 'package.json' does not exist according to earlier cached lookups.",
+    "File '/package.json' does not exist according to earlier cached lookups.",
+    "File 'package.json' does not exist according to earlier cached lookups.",
+    "File '/package.json' does not exist according to earlier cached lookups."
+]
\ No newline at end of file
diff --git a/tests/baselines/reference/nodeModulesExportsBlocksTypesVersions(module=node16).errors.txt b/tests/baselines/reference/nodeModulesExportsBlocksTypesVersions(module=node16).errors.txt
index 22d2482ced9ae..aa450c5fc0c6a 100644
--- a/tests/baselines/reference/nodeModulesExportsBlocksTypesVersions(module=node16).errors.txt
+++ b/tests/baselines/reference/nodeModulesExportsBlocksTypesVersions(module=node16).errors.txt
@@ -8,7 +8,9 @@ error TS6504: File '/node_modules/exports-and-types-versions/dist/foo.js' is a J
 /main.mts(1,16): error TS7016: Could not find a declaration file for module 'exports-and-types-versions/foo'. '/node_modules/exports-and-types-versions/dist/foo.js' implicitly has an 'any' type.
   If the 'exports-and-types-versions' package actually exposes this module, try adding a new declaration (.d.ts) file containing `declare module 'exports-and-types-versions/foo';`
 /main.mts(2,16): error TS2307: Cannot find module 'exports-and-types-versions/nope' or its corresponding type declarations.
+  There are types at '/node_modules/exports-and-types-versions/types/foo.d.ts', but this result could not be resolved when respecting package.json "exports". The 'exports-and-types-versions' library may need to update its package.json.
 /main.mts(5,16): error TS2307: Cannot find module 'exports-and-types-versions/versioned-nah' or its corresponding type declarations.
+  There are types at '/node_modules/exports-and-types-versions/types/foo.d.ts', but this result could not be resolved when respecting package.json "exports". The 'exports-and-types-versions' library may need to update its package.json.
 
 
 !!! error TS6504: File '/node_modules/exports-and-types-versions/dist/foo.js' is a JavaScript file. Did you mean to enable the 'allowJs' option?
@@ -83,10 +85,12 @@ error TS6504: File '/node_modules/exports-and-types-versions/dist/foo.js' is a J
     import {} from "exports-and-types-versions/nope";
                    ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
 !!! error TS2307: Cannot find module 'exports-and-types-versions/nope' or its corresponding type declarations.
+!!! error TS2307:   There are types at '/node_modules/exports-and-types-versions/types/foo.d.ts', but this result could not be resolved when respecting package.json "exports". The 'exports-and-types-versions' library may need to update its package.json.
     import {} from "exports-and-types-versions/yep";
     import {} from "exports-and-types-versions/versioned-yep";
     import {} from "exports-and-types-versions/versioned-nah";
                    ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
 !!! error TS2307: Cannot find module 'exports-and-types-versions/versioned-nah' or its corresponding type declarations.
+!!! error TS2307:   There are types at '/node_modules/exports-and-types-versions/types/foo.d.ts', but this result could not be resolved when respecting package.json "exports". The 'exports-and-types-versions' library may need to update its package.json.
     import {} from "just-types-versions/foo";
     
\ No newline at end of file
diff --git a/tests/baselines/reference/nodeModulesExportsBlocksTypesVersions(module=node16).trace.json b/tests/baselines/reference/nodeModulesExportsBlocksTypesVersions(module=node16).trace.json
index 8c7abd981db3c..ab46ab33214e3 100644
--- a/tests/baselines/reference/nodeModulesExportsBlocksTypesVersions(module=node16).trace.json
+++ b/tests/baselines/reference/nodeModulesExportsBlocksTypesVersions(module=node16).trace.json
@@ -110,6 +110,16 @@
     "Directory '/node_modules/@types' does not exist, skipping all lookups in it.",
     "File '/node_modules/exports-and-types-versions/package.json' exists according to earlier cached lookups.",
     "Export specifier './nope' does not exist in package.json scope at path '/node_modules/exports-and-types-versions'.",
+    "Resolution of non-relative name failed; trying with modern Node resolution features disabled to see if npm library needs configuration update.",
+    "File '/package.json' does not exist according to earlier cached lookups.",
+    "Loading module 'exports-and-types-versions/nope' from 'node_modules' folder, target file types: TypeScript, Declaration.",
+    "File '/node_modules/exports-and-types-versions/package.json' exists according to earlier cached lookups.",
+    "'package.json' has a 'typesVersions' field with version-specific path mappings.",
+    "'package.json' has a 'typesVersions' entry '*' that matches compiler version '3.1.0-dev', looking for a pattern to match module name 'nope'.",
+    "Module name 'nope', matched pattern 'nope'.",
+    "Trying substitution './types/foo.d.ts', candidate module location: './types/foo.d.ts'.",
+    "File '/node_modules/exports-and-types-versions/types/foo.d.ts' exist - use it as a name resolution result.",
+    "Resolving real path for '/node_modules/exports-and-types-versions/types/foo.d.ts', result '/node_modules/exports-and-types-versions/types/foo.d.ts'.",
     "======== Module name 'exports-and-types-versions/nope' was not resolved. ========",
     "======== Resolving module 'exports-and-types-versions/yep' from '/main.mts'. ========",
     "Module resolution kind is not specified, using 'Node16'.",
@@ -145,6 +155,15 @@
     "File '/node_modules/exports-and-types-versions/package.json' exists according to earlier cached lookups.",
     "Saw non-matching condition 'types@<4'.",
     "Export specifier './versioned-nah' does not exist in package.json scope at path '/node_modules/exports-and-types-versions'.",
+    "Resolution of non-relative name failed; trying with modern Node resolution features disabled to see if npm library needs configuration update.",
+    "File '/package.json' does not exist according to earlier cached lookups.",
+    "Loading module 'exports-and-types-versions/versioned-nah' from 'node_modules' folder, target file types: TypeScript, Declaration.",
+    "File '/node_modules/exports-and-types-versions/package.json' exists according to earlier cached lookups.",
+    "'package.json' has a 'typesVersions' entry '*' that matches compiler version '3.1.0-dev', looking for a pattern to match module name 'versioned-nah'.",
+    "Module name 'versioned-nah', matched pattern 'versioned-nah'.",
+    "Trying substitution './types/foo.d.ts', candidate module location: './types/foo.d.ts'.",
+    "File '/node_modules/exports-and-types-versions/types/foo.d.ts' exist - use it as a name resolution result.",
+    "Resolving real path for '/node_modules/exports-and-types-versions/types/foo.d.ts', result '/node_modules/exports-and-types-versions/types/foo.d.ts'.",
     "======== Module name 'exports-and-types-versions/versioned-nah' was not resolved. ========",
     "======== Resolving module 'just-types-versions/foo' from '/main.mts'. ========",
     "Module resolution kind is not specified, using 'Node16'.",
diff --git a/tests/baselines/reference/nodeModulesExportsBlocksTypesVersions(module=nodenext).errors.txt b/tests/baselines/reference/nodeModulesExportsBlocksTypesVersions(module=nodenext).errors.txt
index 22d2482ced9ae..aa450c5fc0c6a 100644
--- a/tests/baselines/reference/nodeModulesExportsBlocksTypesVersions(module=nodenext).errors.txt
+++ b/tests/baselines/reference/nodeModulesExportsBlocksTypesVersions(module=nodenext).errors.txt
@@ -8,7 +8,9 @@ error TS6504: File '/node_modules/exports-and-types-versions/dist/foo.js' is a J
 /main.mts(1,16): error TS7016: Could not find a declaration file for module 'exports-and-types-versions/foo'. '/node_modules/exports-and-types-versions/dist/foo.js' implicitly has an 'any' type.
   If the 'exports-and-types-versions' package actually exposes this module, try adding a new declaration (.d.ts) file containing `declare module 'exports-and-types-versions/foo';`
 /main.mts(2,16): error TS2307: Cannot find module 'exports-and-types-versions/nope' or its corresponding type declarations.
+  There are types at '/node_modules/exports-and-types-versions/types/foo.d.ts', but this result could not be resolved when respecting package.json "exports". The 'exports-and-types-versions' library may need to update its package.json.
 /main.mts(5,16): error TS2307: Cannot find module 'exports-and-types-versions/versioned-nah' or its corresponding type declarations.
+  There are types at '/node_modules/exports-and-types-versions/types/foo.d.ts', but this result could not be resolved when respecting package.json "exports". The 'exports-and-types-versions' library may need to update its package.json.
 
 
 !!! error TS6504: File '/node_modules/exports-and-types-versions/dist/foo.js' is a JavaScript file. Did you mean to enable the 'allowJs' option?
@@ -83,10 +85,12 @@ error TS6504: File '/node_modules/exports-and-types-versions/dist/foo.js' is a J
     import {} from "exports-and-types-versions/nope";
                    ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
 !!! error TS2307: Cannot find module 'exports-and-types-versions/nope' or its corresponding type declarations.
+!!! error TS2307:   There are types at '/node_modules/exports-and-types-versions/types/foo.d.ts', but this result could not be resolved when respecting package.json "exports". The 'exports-and-types-versions' library may need to update its package.json.
     import {} from "exports-and-types-versions/yep";
     import {} from "exports-and-types-versions/versioned-yep";
     import {} from "exports-and-types-versions/versioned-nah";
                    ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
 !!! error TS2307: Cannot find module 'exports-and-types-versions/versioned-nah' or its corresponding type declarations.
+!!! error TS2307:   There are types at '/node_modules/exports-and-types-versions/types/foo.d.ts', but this result could not be resolved when respecting package.json "exports". The 'exports-and-types-versions' library may need to update its package.json.
     import {} from "just-types-versions/foo";
     
\ No newline at end of file
diff --git a/tests/baselines/reference/nodeModulesExportsBlocksTypesVersions(module=nodenext).trace.json b/tests/baselines/reference/nodeModulesExportsBlocksTypesVersions(module=nodenext).trace.json
index 017892d356c35..7274f2bc1a95b 100644
--- a/tests/baselines/reference/nodeModulesExportsBlocksTypesVersions(module=nodenext).trace.json
+++ b/tests/baselines/reference/nodeModulesExportsBlocksTypesVersions(module=nodenext).trace.json
@@ -110,6 +110,16 @@
     "Directory '/node_modules/@types' does not exist, skipping all lookups in it.",
     "File '/node_modules/exports-and-types-versions/package.json' exists according to earlier cached lookups.",
     "Export specifier './nope' does not exist in package.json scope at path '/node_modules/exports-and-types-versions'.",
+    "Resolution of non-relative name failed; trying with modern Node resolution features disabled to see if npm library needs configuration update.",
+    "File '/package.json' does not exist according to earlier cached lookups.",
+    "Loading module 'exports-and-types-versions/nope' from 'node_modules' folder, target file types: TypeScript, Declaration.",
+    "File '/node_modules/exports-and-types-versions/package.json' exists according to earlier cached lookups.",
+    "'package.json' has a 'typesVersions' field with version-specific path mappings.",
+    "'package.json' has a 'typesVersions' entry '*' that matches compiler version '3.1.0-dev', looking for a pattern to match module name 'nope'.",
+    "Module name 'nope', matched pattern 'nope'.",
+    "Trying substitution './types/foo.d.ts', candidate module location: './types/foo.d.ts'.",
+    "File '/node_modules/exports-and-types-versions/types/foo.d.ts' exist - use it as a name resolution result.",
+    "Resolving real path for '/node_modules/exports-and-types-versions/types/foo.d.ts', result '/node_modules/exports-and-types-versions/types/foo.d.ts'.",
     "======== Module name 'exports-and-types-versions/nope' was not resolved. ========",
     "======== Resolving module 'exports-and-types-versions/yep' from '/main.mts'. ========",
     "Module resolution kind is not specified, using 'NodeNext'.",
@@ -145,6 +155,15 @@
     "File '/node_modules/exports-and-types-versions/package.json' exists according to earlier cached lookups.",
     "Saw non-matching condition 'types@<4'.",
     "Export specifier './versioned-nah' does not exist in package.json scope at path '/node_modules/exports-and-types-versions'.",
+    "Resolution of non-relative name failed; trying with modern Node resolution features disabled to see if npm library needs configuration update.",
+    "File '/package.json' does not exist according to earlier cached lookups.",
+    "Loading module 'exports-and-types-versions/versioned-nah' from 'node_modules' folder, target file types: TypeScript, Declaration.",
+    "File '/node_modules/exports-and-types-versions/package.json' exists according to earlier cached lookups.",
+    "'package.json' has a 'typesVersions' entry '*' that matches compiler version '3.1.0-dev', looking for a pattern to match module name 'versioned-nah'.",
+    "Module name 'versioned-nah', matched pattern 'versioned-nah'.",
+    "Trying substitution './types/foo.d.ts', candidate module location: './types/foo.d.ts'.",
+    "File '/node_modules/exports-and-types-versions/types/foo.d.ts' exist - use it as a name resolution result.",
+    "Resolving real path for '/node_modules/exports-and-types-versions/types/foo.d.ts', result '/node_modules/exports-and-types-versions/types/foo.d.ts'.",
     "======== Module name 'exports-and-types-versions/versioned-nah' was not resolved. ========",
     "======== Resolving module 'just-types-versions/foo' from '/main.mts'. ========",
     "Module resolution kind is not specified, using 'NodeNext'.",
diff --git a/tests/baselines/reference/nodeModulesExportsSpecifierGenerationConditions(module=node16).errors.txt b/tests/baselines/reference/nodeModulesExportsSpecifierGenerationConditions(module=node16).errors.txt
index 568ce306b98fd..2fef133f536b8 100644
--- a/tests/baselines/reference/nodeModulesExportsSpecifierGenerationConditions(module=node16).errors.txt
+++ b/tests/baselines/reference/nodeModulesExportsSpecifierGenerationConditions(module=node16).errors.txt
@@ -1,5 +1,6 @@
 error TS2468: Cannot find global value 'Promise'.
 tests/cases/conformance/node/index.ts(2,23): error TS2307: Cannot find module 'inner/other.js' or its corresponding type declarations.
+  There are types at 'tests/cases/conformance/node/node_modules/inner/other.d.ts', but this result could not be resolved when respecting package.json "exports". The 'inner' library may need to update its package.json.
 tests/cases/conformance/node/index.ts(3,19): error TS1378: Top-level 'await' expressions are only allowed when the 'module' option is set to 'es2022', 'esnext', 'system', 'node16', or 'nodenext', and the 'target' option is set to 'es2017' or higher.
 tests/cases/conformance/node/index.ts(3,25): error TS2712: A dynamic import call in ES5/ES3 requires the 'Promise' constructor.  Make sure you have a declaration for the 'Promise' constructor or include 'ES2015' in your '--lib' option.
 
@@ -10,6 +11,7 @@ tests/cases/conformance/node/index.ts(3,25): error TS2712: A dynamic import call
     import { Thing } from "inner/other.js"; // should fail
                           ~~~~~~~~~~~~~~~~
 !!! error TS2307: Cannot find module 'inner/other.js' or its corresponding type declarations.
+!!! error TS2307:   There are types at 'tests/cases/conformance/node/node_modules/inner/other.d.ts', but this result could not be resolved when respecting package.json "exports". The 'inner' library may need to update its package.json.
     export const a = (await import("inner")).x();
                       ~~~~~
 !!! error TS1378: Top-level 'await' expressions are only allowed when the 'module' option is set to 'es2022', 'esnext', 'system', 'node16', or 'nodenext', and the 'target' option is set to 'es2017' or higher.
diff --git a/tests/baselines/reference/nodeModulesExportsSpecifierGenerationConditions(module=nodenext).errors.txt b/tests/baselines/reference/nodeModulesExportsSpecifierGenerationConditions(module=nodenext).errors.txt
index 568ce306b98fd..2fef133f536b8 100644
--- a/tests/baselines/reference/nodeModulesExportsSpecifierGenerationConditions(module=nodenext).errors.txt
+++ b/tests/baselines/reference/nodeModulesExportsSpecifierGenerationConditions(module=nodenext).errors.txt
@@ -1,5 +1,6 @@
 error TS2468: Cannot find global value 'Promise'.
 tests/cases/conformance/node/index.ts(2,23): error TS2307: Cannot find module 'inner/other.js' or its corresponding type declarations.
+  There are types at 'tests/cases/conformance/node/node_modules/inner/other.d.ts', but this result could not be resolved when respecting package.json "exports". The 'inner' library may need to update its package.json.
 tests/cases/conformance/node/index.ts(3,19): error TS1378: Top-level 'await' expressions are only allowed when the 'module' option is set to 'es2022', 'esnext', 'system', 'node16', or 'nodenext', and the 'target' option is set to 'es2017' or higher.
 tests/cases/conformance/node/index.ts(3,25): error TS2712: A dynamic import call in ES5/ES3 requires the 'Promise' constructor.  Make sure you have a declaration for the 'Promise' constructor or include 'ES2015' in your '--lib' option.
 
@@ -10,6 +11,7 @@ tests/cases/conformance/node/index.ts(3,25): error TS2712: A dynamic import call
     import { Thing } from "inner/other.js"; // should fail
                           ~~~~~~~~~~~~~~~~
 !!! error TS2307: Cannot find module 'inner/other.js' or its corresponding type declarations.
+!!! error TS2307:   There are types at 'tests/cases/conformance/node/node_modules/inner/other.d.ts', but this result could not be resolved when respecting package.json "exports". The 'inner' library may need to update its package.json.
     export const a = (await import("inner")).x();
                       ~~~~~
 !!! error TS1378: Top-level 'await' expressions are only allowed when the 'module' option is set to 'es2022', 'esnext', 'system', 'node16', or 'nodenext', and the 'target' option is set to 'es2017' or higher.
diff --git a/tests/baselines/reference/resolvesWithoutExportsDiagnostic1(moduleresolution=bundler).errors.txt b/tests/baselines/reference/resolvesWithoutExportsDiagnostic1(moduleresolution=bundler).errors.txt
new file mode 100644
index 0000000000000..ef8ea52f327c4
--- /dev/null
+++ b/tests/baselines/reference/resolvesWithoutExportsDiagnostic1(moduleresolution=bundler).errors.txt
@@ -0,0 +1,96 @@
+error TS6504: File '/node_modules/bar/index.js' is a JavaScript file. Did you mean to enable the 'allowJs' option?
+  The file is in the program because:
+    Root file specified for compilation
+error TS6504: File '/node_modules/bar/index.mjs' is a JavaScript file. Did you mean to enable the 'allowJs' option?
+  The file is in the program because:
+    Root file specified for compilation
+error TS6504: File '/node_modules/foo/index.js' is a JavaScript file. Did you mean to enable the 'allowJs' option?
+  The file is in the program because:
+    Root file specified for compilation
+error TS6504: File '/node_modules/foo/index.mjs' is a JavaScript file. Did you mean to enable the 'allowJs' option?
+  The file is in the program because:
+    Root file specified for compilation
+/index.mts(1,21): error TS7016: Could not find a declaration file for module 'foo'. '/node_modules/foo/index.mjs' implicitly has an 'any' type.
+  There are types at '/node_modules/foo/index.d.ts', but this result could not be resolved when respecting package.json "exports". The 'foo' library may need to update its package.json.
+/index.mts(2,21): error TS7016: Could not find a declaration file for module 'bar'. '/node_modules/bar/index.mjs' implicitly has an 'any' type.
+  There are types at '/node_modules/@types/bar/index.d.ts', but this result could not be resolved when respecting package.json "exports". The '@types/bar' library may need to update its package.json.
+
+
+!!! error TS6504: File '/node_modules/bar/index.js' is a JavaScript file. Did you mean to enable the 'allowJs' option?
+!!! error TS6504:   The file is in the program because:
+!!! error TS6504:     Root file specified for compilation
+!!! error TS6504: File '/node_modules/bar/index.mjs' is a JavaScript file. Did you mean to enable the 'allowJs' option?
+!!! error TS6504:   The file is in the program because:
+!!! error TS6504:     Root file specified for compilation
+!!! error TS6504: File '/node_modules/foo/index.js' is a JavaScript file. Did you mean to enable the 'allowJs' option?
+!!! error TS6504:   The file is in the program because:
+!!! error TS6504:     Root file specified for compilation
+!!! error TS6504: File '/node_modules/foo/index.mjs' is a JavaScript file. Did you mean to enable the 'allowJs' option?
+!!! error TS6504:   The file is in the program because:
+!!! error TS6504:     Root file specified for compilation
+==== /node_modules/foo/package.json (0 errors) ====
+    {
+        "name": "foo",
+        "version": "1.0.0",
+        "main": "index.js",
+        "types": "index.d.ts",
+        "exports": {
+            ".": {
+                "import": "./index.mjs",
+                "require": "./index.js"
+            }
+        }
+    }
+    
+==== /node_modules/foo/index.js (0 errors) ====
+    module.exports = { foo: 1 };
+    
+==== /node_modules/foo/index.mjs (0 errors) ====
+    export const foo = 1;
+    
+==== /node_modules/foo/index.d.ts (0 errors) ====
+    export declare const foo: number;
+    
+==== /node_modules/@types/bar/package.json (0 errors) ====
+    {
+        "name": "@types/bar",
+        "version": "1.0.0",
+        "types": "index.d.ts",
+        "exports": {
+            ".": {
+                "require": "./index.d.ts"
+            }
+        }
+    }
+    
+==== /node_modules/@types/bar/index.d.ts (0 errors) ====
+    export declare const bar: number;
+    
+==== /node_modules/bar/package.json (0 errors) ====
+    {
+        "name": "bar",
+        "version": "1.0.0",
+        "main": "index.js",
+        "exports": {
+            ".": {
+                "import": "./index.mjs",
+                "require": "./index.js"
+            }
+        }
+    }
+    
+==== /node_modules/bar/index.js (0 errors) ====
+    module.exports = { bar: 1 };
+    
+==== /node_modules/bar/index.mjs (0 errors) ====
+    export const bar = 1;
+    
+==== /index.mts (2 errors) ====
+    import { foo } from "foo";
+                        ~~~~~
+!!! error TS7016: Could not find a declaration file for module 'foo'. '/node_modules/foo/index.mjs' implicitly has an 'any' type.
+!!! error TS7016:   There are types at '/node_modules/foo/index.d.ts', but this result could not be resolved when respecting package.json "exports". The 'foo' library may need to update its package.json.
+    import { bar } from "bar";
+                        ~~~~~
+!!! error TS7016: Could not find a declaration file for module 'bar'. '/node_modules/bar/index.mjs' implicitly has an 'any' type.
+!!! error TS7016:   There are types at '/node_modules/@types/bar/index.d.ts', but this result could not be resolved when respecting package.json "exports". The '@types/bar' library may need to update its package.json.
\ No newline at end of file
diff --git a/tests/baselines/reference/resolvesWithoutExportsDiagnostic1(moduleresolution=bundler).trace.json b/tests/baselines/reference/resolvesWithoutExportsDiagnostic1(moduleresolution=bundler).trace.json
new file mode 100644
index 0000000000000..2859c27f86107
--- /dev/null
+++ b/tests/baselines/reference/resolvesWithoutExportsDiagnostic1(moduleresolution=bundler).trace.json
@@ -0,0 +1,93 @@
+[
+    "======== Resolving module 'foo' from '/index.mts'. ========",
+    "Explicitly specified module resolution kind: 'Bundler'.",
+    "File '/package.json' does not exist.",
+    "Loading module 'foo' from 'node_modules' folder, target file types: TypeScript, JavaScript, Declaration, JSON.",
+    "Found 'package.json' at '/node_modules/foo/package.json'.",
+    "Matched 'exports' condition 'import'.",
+    "Using 'exports' subpath '.' with target './index.mjs'.",
+    "File name '/node_modules/foo/index.mjs' has a '.mjs' extension - stripping it.",
+    "File '/node_modules/foo/index.mts' does not exist.",
+    "File '/node_modules/foo/index.d.mts' does not exist.",
+    "Saw non-matching condition 'require'.",
+    "File '/node_modules/@types/foo.d.ts' does not exist.",
+    "File '/node_modules/foo/package.json' exists according to earlier cached lookups.",
+    "Matched 'exports' condition 'import'.",
+    "Using 'exports' subpath '.' with target './index.mjs'.",
+    "File name '/node_modules/foo/index.mjs' has a '.mjs' extension - stripping it.",
+    "File '/node_modules/foo/index.mjs' exist - use it as a name resolution result.",
+    "Resolving real path for '/node_modules/foo/index.mjs', result '/node_modules/foo/index.mjs'.",
+    "Resolution of non-relative name failed; trying with modern Node resolution features disabled to see if npm library needs configuration update.",
+    "File '/package.json' does not exist according to earlier cached lookups.",
+    "Loading module 'foo' from 'node_modules' folder, target file types: TypeScript, Declaration.",
+    "File '/node_modules/foo/package.json' exists according to earlier cached lookups.",
+    "File '/node_modules/foo.ts' does not exist.",
+    "File '/node_modules/foo.tsx' does not exist.",
+    "File '/node_modules/foo.d.ts' does not exist.",
+    "'package.json' does not have a 'typesVersions' field.",
+    "'package.json' does not have a 'typings' field.",
+    "'package.json' has 'types' field 'index.d.ts' that references '/node_modules/foo/index.d.ts'.",
+    "File '/node_modules/foo/index.d.ts' exist - use it as a name resolution result.",
+    "Resolving real path for '/node_modules/foo/index.d.ts', result '/node_modules/foo/index.d.ts'.",
+    "======== Module name 'foo' was successfully resolved to '/node_modules/foo/index.mjs' with Package ID 'foo/index.mjs@1.0.0'. ========",
+    "======== Resolving module 'bar' from '/index.mts'. ========",
+    "Explicitly specified module resolution kind: 'Bundler'.",
+    "File '/package.json' does not exist according to earlier cached lookups.",
+    "Loading module 'bar' from 'node_modules' folder, target file types: TypeScript, JavaScript, Declaration, JSON.",
+    "Found 'package.json' at '/node_modules/bar/package.json'.",
+    "Matched 'exports' condition 'import'.",
+    "Using 'exports' subpath '.' with target './index.mjs'.",
+    "File name '/node_modules/bar/index.mjs' has a '.mjs' extension - stripping it.",
+    "File '/node_modules/bar/index.mts' does not exist.",
+    "File '/node_modules/bar/index.d.mts' does not exist.",
+    "Saw non-matching condition 'require'.",
+    "Found 'package.json' at '/node_modules/@types/bar/package.json'.",
+    "Saw non-matching condition 'require'.",
+    "File '/node_modules/bar/package.json' exists according to earlier cached lookups.",
+    "Matched 'exports' condition 'import'.",
+    "Using 'exports' subpath '.' with target './index.mjs'.",
+    "File name '/node_modules/bar/index.mjs' has a '.mjs' extension - stripping it.",
+    "File '/node_modules/bar/index.mjs' exist - use it as a name resolution result.",
+    "Resolving real path for '/node_modules/bar/index.mjs', result '/node_modules/bar/index.mjs'.",
+    "Resolution of non-relative name failed; trying with modern Node resolution features disabled to see if npm library needs configuration update.",
+    "File '/package.json' does not exist according to earlier cached lookups.",
+    "Loading module 'bar' from 'node_modules' folder, target file types: TypeScript, Declaration.",
+    "File '/node_modules/bar/package.json' exists according to earlier cached lookups.",
+    "File '/node_modules/bar.ts' does not exist.",
+    "File '/node_modules/bar.tsx' does not exist.",
+    "File '/node_modules/bar.d.ts' does not exist.",
+    "'package.json' does not have a 'typesVersions' field.",
+    "'package.json' does not have a 'typings' field.",
+    "'package.json' does not have a 'types' field.",
+    "'package.json' has 'main' field 'index.js' that references '/node_modules/bar/index.js'.",
+    "File '/node_modules/bar/index.js' exist - use it as a name resolution result.",
+    "File '/node_modules/bar/index.js' has an unsupported extension, so skipping it.",
+    "Loading module as file / folder, candidate module location '/node_modules/bar/index.js', target file types: TypeScript, Declaration.",
+    "File name '/node_modules/bar/index.js' has a '.js' extension - stripping it.",
+    "File '/node_modules/bar/index.ts' does not exist.",
+    "File '/node_modules/bar/index.tsx' does not exist.",
+    "File '/node_modules/bar/index.d.ts' does not exist.",
+    "File '/node_modules/bar/index.js.ts' does not exist.",
+    "File '/node_modules/bar/index.js.tsx' does not exist.",
+    "File '/node_modules/bar/index.js.d.ts' does not exist.",
+    "Directory '/node_modules/bar/index.js' does not exist, skipping all lookups in it.",
+    "File '/node_modules/bar/index.ts' does not exist.",
+    "File '/node_modules/bar/index.tsx' does not exist.",
+    "File '/node_modules/bar/index.d.ts' does not exist.",
+    "File '/node_modules/@types/bar/package.json' exists according to earlier cached lookups.",
+    "File '/node_modules/@types/bar.d.ts' does not exist.",
+    "'package.json' does not have a 'typesVersions' field.",
+    "'package.json' does not have a 'typings' field.",
+    "'package.json' has 'types' field 'index.d.ts' that references '/node_modules/@types/bar/index.d.ts'.",
+    "File '/node_modules/@types/bar/index.d.ts' exist - use it as a name resolution result.",
+    "Resolving real path for '/node_modules/@types/bar/index.d.ts', result '/node_modules/@types/bar/index.d.ts'.",
+    "======== Module name 'bar' was successfully resolved to '/node_modules/bar/index.mjs' with Package ID 'bar/index.mjs@1.0.0'. ========",
+    "======== Resolving type reference directive 'bar', containing file '__inferred type names__.ts', root directory '/node_modules/@types'. ========",
+    "Resolving with primary search path '/node_modules/@types'.",
+    "File '/node_modules/@types/bar/package.json' exists according to earlier cached lookups.",
+    "'package.json' does not have a 'typings' field.",
+    "'package.json' has 'types' field 'index.d.ts' that references '/node_modules/@types/bar/index.d.ts'.",
+    "File '/node_modules/@types/bar/index.d.ts' exist - use it as a name resolution result.",
+    "Resolving real path for '/node_modules/@types/bar/index.d.ts', result '/node_modules/@types/bar/index.d.ts'.",
+    "======== Type reference directive 'bar' was successfully resolved to '/node_modules/@types/bar/index.d.ts' with Package ID '@types/bar/index.d.ts@1.0.0', primary: true. ========"
+]
\ No newline at end of file
diff --git a/tests/baselines/reference/resolvesWithoutExportsDiagnostic1(moduleresolution=node16).errors.txt b/tests/baselines/reference/resolvesWithoutExportsDiagnostic1(moduleresolution=node16).errors.txt
new file mode 100644
index 0000000000000..ef8ea52f327c4
--- /dev/null
+++ b/tests/baselines/reference/resolvesWithoutExportsDiagnostic1(moduleresolution=node16).errors.txt
@@ -0,0 +1,96 @@
+error TS6504: File '/node_modules/bar/index.js' is a JavaScript file. Did you mean to enable the 'allowJs' option?
+  The file is in the program because:
+    Root file specified for compilation
+error TS6504: File '/node_modules/bar/index.mjs' is a JavaScript file. Did you mean to enable the 'allowJs' option?
+  The file is in the program because:
+    Root file specified for compilation
+error TS6504: File '/node_modules/foo/index.js' is a JavaScript file. Did you mean to enable the 'allowJs' option?
+  The file is in the program because:
+    Root file specified for compilation
+error TS6504: File '/node_modules/foo/index.mjs' is a JavaScript file. Did you mean to enable the 'allowJs' option?
+  The file is in the program because:
+    Root file specified for compilation
+/index.mts(1,21): error TS7016: Could not find a declaration file for module 'foo'. '/node_modules/foo/index.mjs' implicitly has an 'any' type.
+  There are types at '/node_modules/foo/index.d.ts', but this result could not be resolved when respecting package.json "exports". The 'foo' library may need to update its package.json.
+/index.mts(2,21): error TS7016: Could not find a declaration file for module 'bar'. '/node_modules/bar/index.mjs' implicitly has an 'any' type.
+  There are types at '/node_modules/@types/bar/index.d.ts', but this result could not be resolved when respecting package.json "exports". The '@types/bar' library may need to update its package.json.
+
+
+!!! error TS6504: File '/node_modules/bar/index.js' is a JavaScript file. Did you mean to enable the 'allowJs' option?
+!!! error TS6504:   The file is in the program because:
+!!! error TS6504:     Root file specified for compilation
+!!! error TS6504: File '/node_modules/bar/index.mjs' is a JavaScript file. Did you mean to enable the 'allowJs' option?
+!!! error TS6504:   The file is in the program because:
+!!! error TS6504:     Root file specified for compilation
+!!! error TS6504: File '/node_modules/foo/index.js' is a JavaScript file. Did you mean to enable the 'allowJs' option?
+!!! error TS6504:   The file is in the program because:
+!!! error TS6504:     Root file specified for compilation
+!!! error TS6504: File '/node_modules/foo/index.mjs' is a JavaScript file. Did you mean to enable the 'allowJs' option?
+!!! error TS6504:   The file is in the program because:
+!!! error TS6504:     Root file specified for compilation
+==== /node_modules/foo/package.json (0 errors) ====
+    {
+        "name": "foo",
+        "version": "1.0.0",
+        "main": "index.js",
+        "types": "index.d.ts",
+        "exports": {
+            ".": {
+                "import": "./index.mjs",
+                "require": "./index.js"
+            }
+        }
+    }
+    
+==== /node_modules/foo/index.js (0 errors) ====
+    module.exports = { foo: 1 };
+    
+==== /node_modules/foo/index.mjs (0 errors) ====
+    export const foo = 1;
+    
+==== /node_modules/foo/index.d.ts (0 errors) ====
+    export declare const foo: number;
+    
+==== /node_modules/@types/bar/package.json (0 errors) ====
+    {
+        "name": "@types/bar",
+        "version": "1.0.0",
+        "types": "index.d.ts",
+        "exports": {
+            ".": {
+                "require": "./index.d.ts"
+            }
+        }
+    }
+    
+==== /node_modules/@types/bar/index.d.ts (0 errors) ====
+    export declare const bar: number;
+    
+==== /node_modules/bar/package.json (0 errors) ====
+    {
+        "name": "bar",
+        "version": "1.0.0",
+        "main": "index.js",
+        "exports": {
+            ".": {
+                "import": "./index.mjs",
+                "require": "./index.js"
+            }
+        }
+    }
+    
+==== /node_modules/bar/index.js (0 errors) ====
+    module.exports = { bar: 1 };
+    
+==== /node_modules/bar/index.mjs (0 errors) ====
+    export const bar = 1;
+    
+==== /index.mts (2 errors) ====
+    import { foo } from "foo";
+                        ~~~~~
+!!! error TS7016: Could not find a declaration file for module 'foo'. '/node_modules/foo/index.mjs' implicitly has an 'any' type.
+!!! error TS7016:   There are types at '/node_modules/foo/index.d.ts', but this result could not be resolved when respecting package.json "exports". The 'foo' library may need to update its package.json.
+    import { bar } from "bar";
+                        ~~~~~
+!!! error TS7016: Could not find a declaration file for module 'bar'. '/node_modules/bar/index.mjs' implicitly has an 'any' type.
+!!! error TS7016:   There are types at '/node_modules/@types/bar/index.d.ts', but this result could not be resolved when respecting package.json "exports". The '@types/bar' library may need to update its package.json.
\ No newline at end of file
diff --git a/tests/baselines/reference/resolvesWithoutExportsDiagnostic1(moduleresolution=node16).trace.json b/tests/baselines/reference/resolvesWithoutExportsDiagnostic1(moduleresolution=node16).trace.json
new file mode 100644
index 0000000000000..6d8b992bfbc76
--- /dev/null
+++ b/tests/baselines/reference/resolvesWithoutExportsDiagnostic1(moduleresolution=node16).trace.json
@@ -0,0 +1,96 @@
+[
+    "Found 'package.json' at '/node_modules/foo/package.json'.",
+    "Found 'package.json' at '/node_modules/@types/bar/package.json'.",
+    "======== Resolving module 'foo' from '/index.mts'. ========",
+    "Explicitly specified module resolution kind: 'Node16'.",
+    "Resolving in ESM mode with conditions 'node', 'import', 'types'.",
+    "File '/package.json' does not exist.",
+    "Loading module 'foo' from 'node_modules' folder, target file types: TypeScript, JavaScript, Declaration.",
+    "File '/node_modules/foo/package.json' exists according to earlier cached lookups.",
+    "Matched 'exports' condition 'import'.",
+    "Using 'exports' subpath '.' with target './index.mjs'.",
+    "File name '/node_modules/foo/index.mjs' has a '.mjs' extension - stripping it.",
+    "File '/node_modules/foo/index.mts' does not exist.",
+    "File '/node_modules/foo/index.d.mts' does not exist.",
+    "Saw non-matching condition 'require'.",
+    "File '/node_modules/foo/package.json' exists according to earlier cached lookups.",
+    "Matched 'exports' condition 'import'.",
+    "Using 'exports' subpath '.' with target './index.mjs'.",
+    "File name '/node_modules/foo/index.mjs' has a '.mjs' extension - stripping it.",
+    "File '/node_modules/foo/index.mjs' exist - use it as a name resolution result.",
+    "Resolving real path for '/node_modules/foo/index.mjs', result '/node_modules/foo/index.mjs'.",
+    "Resolution of non-relative name failed; trying with modern Node resolution features disabled to see if npm library needs configuration update.",
+    "File '/package.json' does not exist according to earlier cached lookups.",
+    "Loading module 'foo' from 'node_modules' folder, target file types: TypeScript, Declaration.",
+    "File '/node_modules/foo/package.json' exists according to earlier cached lookups.",
+    "'package.json' does not have a 'typesVersions' field.",
+    "'package.json' does not have a 'typings' field.",
+    "'package.json' has 'types' field 'index.d.ts' that references '/node_modules/foo/index.d.ts'.",
+    "File '/node_modules/foo/index.d.ts' exist - use it as a name resolution result.",
+    "Resolving real path for '/node_modules/foo/index.d.ts', result '/node_modules/foo/index.d.ts'.",
+    "======== Module name 'foo' was successfully resolved to '/node_modules/foo/index.mjs' with Package ID 'foo/index.mjs@1.0.0'. ========",
+    "======== Resolving module 'bar' from '/index.mts'. ========",
+    "Explicitly specified module resolution kind: 'Node16'.",
+    "Resolving in ESM mode with conditions 'node', 'import', 'types'.",
+    "File '/package.json' does not exist according to earlier cached lookups.",
+    "Loading module 'bar' from 'node_modules' folder, target file types: TypeScript, JavaScript, Declaration.",
+    "Found 'package.json' at '/node_modules/bar/package.json'.",
+    "Matched 'exports' condition 'import'.",
+    "Using 'exports' subpath '.' with target './index.mjs'.",
+    "File name '/node_modules/bar/index.mjs' has a '.mjs' extension - stripping it.",
+    "File '/node_modules/bar/index.mts' does not exist.",
+    "File '/node_modules/bar/index.d.mts' does not exist.",
+    "Saw non-matching condition 'require'.",
+    "File '/node_modules/@types/bar/package.json' exists according to earlier cached lookups.",
+    "Saw non-matching condition 'require'.",
+    "File '/node_modules/bar/package.json' exists according to earlier cached lookups.",
+    "Matched 'exports' condition 'import'.",
+    "Using 'exports' subpath '.' with target './index.mjs'.",
+    "File name '/node_modules/bar/index.mjs' has a '.mjs' extension - stripping it.",
+    "File '/node_modules/bar/index.mjs' exist - use it as a name resolution result.",
+    "Resolving real path for '/node_modules/bar/index.mjs', result '/node_modules/bar/index.mjs'.",
+    "Resolution of non-relative name failed; trying with modern Node resolution features disabled to see if npm library needs configuration update.",
+    "File '/package.json' does not exist according to earlier cached lookups.",
+    "Loading module 'bar' from 'node_modules' folder, target file types: TypeScript, Declaration.",
+    "File '/node_modules/bar/package.json' exists according to earlier cached lookups.",
+    "'package.json' does not have a 'typesVersions' field.",
+    "'package.json' does not have a 'typings' field.",
+    "'package.json' does not have a 'types' field.",
+    "'package.json' has 'main' field 'index.js' that references '/node_modules/bar/index.js'.",
+    "File '/node_modules/bar/index.js' exist - use it as a name resolution result.",
+    "File '/node_modules/bar/index.js' has an unsupported extension, so skipping it.",
+    "Loading module as file / folder, candidate module location '/node_modules/bar/index.js', target file types: TypeScript, Declaration.",
+    "File name '/node_modules/bar/index.js' has a '.js' extension - stripping it.",
+    "File '/node_modules/bar/index.ts' does not exist.",
+    "File '/node_modules/bar/index.tsx' does not exist.",
+    "File '/node_modules/bar/index.d.ts' does not exist.",
+    "File '/node_modules/bar/index.js.ts' does not exist.",
+    "File '/node_modules/bar/index.js.tsx' does not exist.",
+    "File '/node_modules/bar/index.js.d.ts' does not exist.",
+    "Directory '/node_modules/bar/index.js' does not exist, skipping all lookups in it.",
+    "File '/node_modules/@types/bar/package.json' exists according to earlier cached lookups.",
+    "'package.json' does not have a 'typesVersions' field.",
+    "'package.json' does not have a 'typings' field.",
+    "'package.json' has 'types' field 'index.d.ts' that references '/node_modules/@types/bar/index.d.ts'.",
+    "File '/node_modules/@types/bar/index.d.ts' exist - use it as a name resolution result.",
+    "Resolving real path for '/node_modules/@types/bar/index.d.ts', result '/node_modules/@types/bar/index.d.ts'.",
+    "======== Module name 'bar' was successfully resolved to '/node_modules/bar/index.mjs' with Package ID 'bar/index.mjs@1.0.0'. ========",
+    "======== Resolving type reference directive 'bar', containing file '__inferred type names__.ts', root directory '/node_modules/@types'. ========",
+    "Resolving with primary search path '/node_modules/@types'.",
+    "File '/node_modules/@types/bar/package.json' exists according to earlier cached lookups.",
+    "'package.json' does not have a 'typings' field.",
+    "'package.json' has 'types' field 'index.d.ts' that references '/node_modules/@types/bar/index.d.ts'.",
+    "File '/node_modules/@types/bar/index.d.ts' exist - use it as a name resolution result.",
+    "Resolving real path for '/node_modules/@types/bar/index.d.ts', result '/node_modules/@types/bar/index.d.ts'.",
+    "======== Type reference directive 'bar' was successfully resolved to '/node_modules/@types/bar/index.d.ts' with Package ID '@types/bar/index.d.ts@1.0.0', primary: true. ========",
+    "File 'package.json' does not exist.",
+    "File '/package.json' does not exist according to earlier cached lookups.",
+    "File 'package.json' does not exist according to earlier cached lookups.",
+    "File '/package.json' does not exist according to earlier cached lookups.",
+    "File 'package.json' does not exist according to earlier cached lookups.",
+    "File '/package.json' does not exist according to earlier cached lookups.",
+    "File 'package.json' does not exist according to earlier cached lookups.",
+    "File '/package.json' does not exist according to earlier cached lookups.",
+    "File 'package.json' does not exist according to earlier cached lookups.",
+    "File '/package.json' does not exist according to earlier cached lookups."
+]
\ No newline at end of file
diff --git a/tests/cases/conformance/moduleResolution/nestedPackageJsonRedirect.ts b/tests/cases/conformance/moduleResolution/nestedPackageJsonRedirect.ts
new file mode 100644
index 0000000000000..8d5804c1fd010
--- /dev/null
+++ b/tests/cases/conformance/moduleResolution/nestedPackageJsonRedirect.ts
@@ -0,0 +1,29 @@
+// @moduleResolution: node16,nodenext,bundler
+// @noEmit: true
+// @noTypesAndSymbols: true
+// @traceResolution: true
+// @strict: true
+
+// @Filename: /node_modules/@restart/hooks/package.json
+{
+    "name": "@restart/hooks",
+    "version": "0.3.25",
+    "main": "cjs/index.js",
+    "types": "cjs/index.d.ts",
+    "module": "esm/index.js"
+}
+
+// @Filename: /node_modules/@restart/hooks/useMergedRefs/package.json
+{
+    "name": "@restart/hooks/useMergedRefs",
+    "private": true,
+    "main": "../cjs/useMergedRefs.js",
+    "module": "../esm/useMergedRefs.js",
+    "types": "../esm/useMergedRefs.d.ts"
+  }
+
+// @Filename: /node_modules/@restart/hooks/esm/useMergedRefs.d.ts
+export {};
+
+// @Filename: /main.ts
+import {} from "@restart/hooks/useMergedRefs";
diff --git a/tests/cases/conformance/moduleResolution/resolvesWithoutExportsDiagnostic1.ts b/tests/cases/conformance/moduleResolution/resolvesWithoutExportsDiagnostic1.ts
new file mode 100644
index 0000000000000..d01bb47a75ca8
--- /dev/null
+++ b/tests/cases/conformance/moduleResolution/resolvesWithoutExportsDiagnostic1.ts
@@ -0,0 +1,66 @@
+// @moduleResolution: bundler,node16
+// @strict: true
+// @noTypesAndSymbols: true
+// @noEmit: true
+// @traceResolution: true
+
+// @Filename: /node_modules/foo/package.json
+{
+    "name": "foo",
+    "version": "1.0.0",
+    "main": "index.js",
+    "types": "index.d.ts",
+    "exports": {
+        ".": {
+            "import": "./index.mjs",
+            "require": "./index.js"
+        }
+    }
+}
+
+// @Filename: /node_modules/foo/index.js
+module.exports = { foo: 1 };
+
+// @Filename: /node_modules/foo/index.mjs
+export const foo = 1;
+
+// @Filename: /node_modules/foo/index.d.ts
+export declare const foo: number;
+
+// @Filename: /node_modules/@types/bar/package.json
+{
+    "name": "@types/bar",
+    "version": "1.0.0",
+    "types": "index.d.ts",
+    "exports": {
+        ".": {
+            "require": "./index.d.ts"
+        }
+    }
+}
+
+// @Filename: /node_modules/@types/bar/index.d.ts
+export declare const bar: number;
+
+// @Filename: /node_modules/bar/package.json
+{
+    "name": "bar",
+    "version": "1.0.0",
+    "main": "index.js",
+    "exports": {
+        ".": {
+            "import": "./index.mjs",
+            "require": "./index.js"
+        }
+    }
+}
+
+// @Filename: /node_modules/bar/index.js
+module.exports = { bar: 1 };
+
+// @Filename: /node_modules/bar/index.mjs
+export const bar = 1;
+
+// @Filename: /index.mts
+import { foo } from "foo";
+import { bar } from "bar";
\ No newline at end of file