diff --git a/src/compiler/moduleNameResolver.ts b/src/compiler/moduleNameResolver.ts
index 30cbc37fd14e9..332804c7d43df 100644
--- a/src/compiler/moduleNameResolver.ts
+++ b/src/compiler/moduleNameResolver.ts
@@ -259,6 +259,7 @@ export interface ModuleResolutionState {
     requestContainingDirectory: string | undefined;
     reportDiagnostic: DiagnosticReporter;
     isConfigLookup: boolean;
+    candidateIsFromPackageJsonField: boolean;
 }
 
 /** Just the fields that we use for module resolution.
@@ -526,6 +527,7 @@ export function resolveTypeReferenceDirective(typeReferenceDirectiveName: string
         requestContainingDirectory: containingDirectory,
         reportDiagnostic: diag => void diagnostics.push(diag),
         isConfigLookup: false,
+        candidateIsFromPackageJsonField: false,
     };
     let resolved = primaryLookup();
     let primary = true;
@@ -1652,6 +1654,7 @@ function nodeModuleNameResolverWorker(features: NodeResolutionFeatures, moduleNa
         requestContainingDirectory: containingDirectory,
         reportDiagnostic: diag => void diagnostics.push(diag),
         isConfigLookup,
+        candidateIsFromPackageJsonField: false,
     };
 
     if (traceEnabled && getEmitModuleResolutionKind(compilerOptions) >= ModuleResolutionKind.Node16 && getEmitModuleResolutionKind(compilerOptions) <= ModuleResolutionKind.NodeNext) {
@@ -1948,7 +1951,7 @@ function tryAddingExtensions(candidate: string, extensions: Extensions, original
 
     function tryExtension(ext: string, resolvedUsingTsExtension?: boolean): PathAndExtension | undefined {
         const path = tryFile(candidate + ext, onlyRecordFailures, state);
-        return path === undefined ? undefined : { path, ext, resolvedUsingTsExtension };
+        return path === undefined ? undefined : { path, ext, resolvedUsingTsExtension: !state.candidateIsFromPackageJsonField && resolvedUsingTsExtension };
     }
 }
 
@@ -2111,6 +2114,7 @@ export function getTemporaryModuleResolutionState(packageJsonInfoCache: PackageJ
         requestContainingDirectory: undefined,
         reportDiagnostic: noop,
         isConfigLookup: false,
+        candidateIsFromPackageJsonField: false,
     };
 }
 
@@ -2232,11 +2236,14 @@ function loadNodeModuleFromDirectoryWorker(extensions: Extensions, candidate: st
         // (technically it only emits a deprecation warning in esm packages right now, but that's probably
         // enough to mean we don't need to support it)
         const features = state.features;
+        const candidateIsFromPackageJsonField = state.candidateIsFromPackageJsonField;
+        state.candidateIsFromPackageJsonField = true;
         if (jsonContent?.type !== "module") {
             state.features &= ~NodeResolutionFeatures.EsmMode;
         }
         const result = nodeLoadModuleByRelativeName(expandedExtensions, candidate, onlyRecordFailures, state, /*considerPackageJson*/ false);
         state.features = features;
+        state.candidateIsFromPackageJsonField = candidateIsFromPackageJsonField;
         return result;
     };
 
@@ -2935,6 +2942,7 @@ export function classicNameResolver(moduleName: string, containingFile: string,
         requestContainingDirectory: containingDirectory,
         reportDiagnostic: diag => void diagnostics.push(diag),
         isConfigLookup: false,
+        candidateIsFromPackageJsonField: false,
     };
 
     const resolved =
@@ -3015,6 +3023,7 @@ export function loadModuleFromGlobalCache(moduleName: string, projectName: strin
         requestContainingDirectory: undefined,
         reportDiagnostic: diag => void diagnostics.push(diag),
         isConfigLookup: false,
+        candidateIsFromPackageJsonField: false,
     };
     const resolved = loadModuleFromImmediateNodeModulesDirectory(Extensions.Declaration, moduleName, globalCache, state, /*typesScopeOnly*/ false, /*cache*/ undefined, /*redirectedReference*/ undefined);
     return createResolvedModuleWithFailedLookupLocations(
diff --git a/tests/baselines/reference/resolutionCandidateFromPackageJsonField1.js b/tests/baselines/reference/resolutionCandidateFromPackageJsonField1.js
new file mode 100644
index 0000000000000..094f3a3dd9e7a
--- /dev/null
+++ b/tests/baselines/reference/resolutionCandidateFromPackageJsonField1.js
@@ -0,0 +1,22 @@
+//// [tests/cases/compiler/resolutionCandidateFromPackageJsonField1.ts] ////
+
+//// [package.json]
+{
+    "name": "@angular/core",
+    "typings": "index.d.ts"
+}
+
+//// [index.ts]
+export {};
+
+//// [test.ts]
+import "@angular/core";
+
+
+//// [index.js]
+"use strict";
+Object.defineProperty(exports, "__esModule", { value: true });
+//// [test.js]
+"use strict";
+Object.defineProperty(exports, "__esModule", { value: true });
+require("@angular/core");
diff --git a/tests/baselines/reference/resolutionCandidateFromPackageJsonField1.symbols b/tests/baselines/reference/resolutionCandidateFromPackageJsonField1.symbols
new file mode 100644
index 0000000000000..c696908e16a5f
--- /dev/null
+++ b/tests/baselines/reference/resolutionCandidateFromPackageJsonField1.symbols
@@ -0,0 +1,8 @@
+=== tests/cases/compiler/@angular/core/index.ts ===
+
+export {};
+
+=== tests/cases/compiler/@angular/core/testing/test.ts ===
+
+import "@angular/core";
+
diff --git a/tests/baselines/reference/resolutionCandidateFromPackageJsonField1.types b/tests/baselines/reference/resolutionCandidateFromPackageJsonField1.types
new file mode 100644
index 0000000000000..c696908e16a5f
--- /dev/null
+++ b/tests/baselines/reference/resolutionCandidateFromPackageJsonField1.types
@@ -0,0 +1,8 @@
+=== tests/cases/compiler/@angular/core/index.ts ===
+
+export {};
+
+=== tests/cases/compiler/@angular/core/testing/test.ts ===
+
+import "@angular/core";
+
diff --git a/tests/baselines/reference/resolutionCandidateFromPackageJsonField2(moduleresolution=bundler).errors.txt b/tests/baselines/reference/resolutionCandidateFromPackageJsonField2(moduleresolution=bundler).errors.txt
new file mode 100644
index 0000000000000..ef3ffa721e4ea
--- /dev/null
+++ b/tests/baselines/reference/resolutionCandidateFromPackageJsonField2(moduleresolution=bundler).errors.txt
@@ -0,0 +1,25 @@
+tests/cases/compiler/test.ts(1,19): error TS5097: An import path can only end with a '.ts' extension when 'allowImportingTsExtensions' is enabled.
+
+
+==== tests/cases/compiler/tsconfig.json (0 errors) ====
+    {
+        "compilerOptions": {
+            "paths": {
+                "foo/*": ["./dist/*"],
+                "baz/*.ts": ["./types/*.d.ts"]
+            }
+        }
+    }
+    
+==== tests/cases/compiler/dist/bar.ts (0 errors) ====
+    export const a = 1234;
+    
+==== tests/cases/compiler/types/main.d.ts (0 errors) ====
+    export const b: string;
+    
+==== tests/cases/compiler/test.ts (1 errors) ====
+    import { a } from "foo/bar.ts";
+                      ~~~~~~~~~~~~
+!!! error TS5097: An import path can only end with a '.ts' extension when 'allowImportingTsExtensions' is enabled.
+    import { b } from "baz/main.ts";
+    
\ No newline at end of file
diff --git a/tests/baselines/reference/resolutionCandidateFromPackageJsonField2(moduleresolution=bundler).js b/tests/baselines/reference/resolutionCandidateFromPackageJsonField2(moduleresolution=bundler).js
new file mode 100644
index 0000000000000..fc322d5465d3d
--- /dev/null
+++ b/tests/baselines/reference/resolutionCandidateFromPackageJsonField2(moduleresolution=bundler).js
@@ -0,0 +1,21 @@
+//// [tests/cases/compiler/resolutionCandidateFromPackageJsonField2.ts] ////
+
+//// [bar.ts]
+export const a = 1234;
+
+//// [main.d.ts]
+export const b: string;
+
+//// [test.ts]
+import { a } from "foo/bar.ts";
+import { b } from "baz/main.ts";
+
+
+//// [bar.js]
+"use strict";
+Object.defineProperty(exports, "__esModule", { value: true });
+exports.a = void 0;
+exports.a = 1234;
+//// [test.js]
+"use strict";
+Object.defineProperty(exports, "__esModule", { value: true });
diff --git a/tests/baselines/reference/resolutionCandidateFromPackageJsonField2(moduleresolution=bundler).symbols b/tests/baselines/reference/resolutionCandidateFromPackageJsonField2(moduleresolution=bundler).symbols
new file mode 100644
index 0000000000000..4418c58121945
--- /dev/null
+++ b/tests/baselines/reference/resolutionCandidateFromPackageJsonField2(moduleresolution=bundler).symbols
@@ -0,0 +1,15 @@
+=== tests/cases/compiler/dist/bar.ts ===
+export const a = 1234;
+>a : Symbol(a, Decl(bar.ts, 0, 12))
+
+=== tests/cases/compiler/types/main.d.ts ===
+export const b: string;
+>b : Symbol(b, Decl(main.d.ts, 0, 12))
+
+=== tests/cases/compiler/test.ts ===
+import { a } from "foo/bar.ts";
+>a : Symbol(a, Decl(test.ts, 0, 8))
+
+import { b } from "baz/main.ts";
+>b : Symbol(b, Decl(test.ts, 1, 8))
+
diff --git a/tests/baselines/reference/resolutionCandidateFromPackageJsonField2(moduleresolution=bundler).types b/tests/baselines/reference/resolutionCandidateFromPackageJsonField2(moduleresolution=bundler).types
new file mode 100644
index 0000000000000..1687bb192d5de
--- /dev/null
+++ b/tests/baselines/reference/resolutionCandidateFromPackageJsonField2(moduleresolution=bundler).types
@@ -0,0 +1,16 @@
+=== tests/cases/compiler/dist/bar.ts ===
+export const a = 1234;
+>a : 1234
+>1234 : 1234
+
+=== tests/cases/compiler/types/main.d.ts ===
+export const b: string;
+>b : string
+
+=== tests/cases/compiler/test.ts ===
+import { a } from "foo/bar.ts";
+>a : 1234
+
+import { b } from "baz/main.ts";
+>b : string
+
diff --git a/tests/baselines/reference/resolutionCandidateFromPackageJsonField2(moduleresolution=node10).errors.txt b/tests/baselines/reference/resolutionCandidateFromPackageJsonField2(moduleresolution=node10).errors.txt
new file mode 100644
index 0000000000000..ef3ffa721e4ea
--- /dev/null
+++ b/tests/baselines/reference/resolutionCandidateFromPackageJsonField2(moduleresolution=node10).errors.txt
@@ -0,0 +1,25 @@
+tests/cases/compiler/test.ts(1,19): error TS5097: An import path can only end with a '.ts' extension when 'allowImportingTsExtensions' is enabled.
+
+
+==== tests/cases/compiler/tsconfig.json (0 errors) ====
+    {
+        "compilerOptions": {
+            "paths": {
+                "foo/*": ["./dist/*"],
+                "baz/*.ts": ["./types/*.d.ts"]
+            }
+        }
+    }
+    
+==== tests/cases/compiler/dist/bar.ts (0 errors) ====
+    export const a = 1234;
+    
+==== tests/cases/compiler/types/main.d.ts (0 errors) ====
+    export const b: string;
+    
+==== tests/cases/compiler/test.ts (1 errors) ====
+    import { a } from "foo/bar.ts";
+                      ~~~~~~~~~~~~
+!!! error TS5097: An import path can only end with a '.ts' extension when 'allowImportingTsExtensions' is enabled.
+    import { b } from "baz/main.ts";
+    
\ No newline at end of file
diff --git a/tests/baselines/reference/resolutionCandidateFromPackageJsonField2(moduleresolution=node10).js b/tests/baselines/reference/resolutionCandidateFromPackageJsonField2(moduleresolution=node10).js
new file mode 100644
index 0000000000000..fc322d5465d3d
--- /dev/null
+++ b/tests/baselines/reference/resolutionCandidateFromPackageJsonField2(moduleresolution=node10).js
@@ -0,0 +1,21 @@
+//// [tests/cases/compiler/resolutionCandidateFromPackageJsonField2.ts] ////
+
+//// [bar.ts]
+export const a = 1234;
+
+//// [main.d.ts]
+export const b: string;
+
+//// [test.ts]
+import { a } from "foo/bar.ts";
+import { b } from "baz/main.ts";
+
+
+//// [bar.js]
+"use strict";
+Object.defineProperty(exports, "__esModule", { value: true });
+exports.a = void 0;
+exports.a = 1234;
+//// [test.js]
+"use strict";
+Object.defineProperty(exports, "__esModule", { value: true });
diff --git a/tests/baselines/reference/resolutionCandidateFromPackageJsonField2(moduleresolution=node10).symbols b/tests/baselines/reference/resolutionCandidateFromPackageJsonField2(moduleresolution=node10).symbols
new file mode 100644
index 0000000000000..4418c58121945
--- /dev/null
+++ b/tests/baselines/reference/resolutionCandidateFromPackageJsonField2(moduleresolution=node10).symbols
@@ -0,0 +1,15 @@
+=== tests/cases/compiler/dist/bar.ts ===
+export const a = 1234;
+>a : Symbol(a, Decl(bar.ts, 0, 12))
+
+=== tests/cases/compiler/types/main.d.ts ===
+export const b: string;
+>b : Symbol(b, Decl(main.d.ts, 0, 12))
+
+=== tests/cases/compiler/test.ts ===
+import { a } from "foo/bar.ts";
+>a : Symbol(a, Decl(test.ts, 0, 8))
+
+import { b } from "baz/main.ts";
+>b : Symbol(b, Decl(test.ts, 1, 8))
+
diff --git a/tests/baselines/reference/resolutionCandidateFromPackageJsonField2(moduleresolution=node10).types b/tests/baselines/reference/resolutionCandidateFromPackageJsonField2(moduleresolution=node10).types
new file mode 100644
index 0000000000000..1687bb192d5de
--- /dev/null
+++ b/tests/baselines/reference/resolutionCandidateFromPackageJsonField2(moduleresolution=node10).types
@@ -0,0 +1,16 @@
+=== tests/cases/compiler/dist/bar.ts ===
+export const a = 1234;
+>a : 1234
+>1234 : 1234
+
+=== tests/cases/compiler/types/main.d.ts ===
+export const b: string;
+>b : string
+
+=== tests/cases/compiler/test.ts ===
+import { a } from "foo/bar.ts";
+>a : 1234
+
+import { b } from "baz/main.ts";
+>b : string
+
diff --git a/tests/cases/compiler/resolutionCandidateFromPackageJsonField1.ts b/tests/cases/compiler/resolutionCandidateFromPackageJsonField1.ts
new file mode 100644
index 0000000000000..800ec19a53bfe
--- /dev/null
+++ b/tests/cases/compiler/resolutionCandidateFromPackageJsonField1.ts
@@ -0,0 +1,20 @@
+// @filename: tsconfig.json
+{
+    "compilerOptions": {
+        "paths": {
+            "@angular/*": ["./@angular/*"]
+        }
+    }
+}
+
+// @filename: @angular/core/package.json
+{
+    "name": "@angular/core",
+    "typings": "index.d.ts"
+}
+
+// @filename: @angular/core/index.ts
+export {};
+
+// @filename: @angular/core/testing/test.ts
+import "@angular/core";
diff --git a/tests/cases/compiler/resolutionCandidateFromPackageJsonField2.ts b/tests/cases/compiler/resolutionCandidateFromPackageJsonField2.ts
new file mode 100644
index 0000000000000..c1e30c89e5b9d
--- /dev/null
+++ b/tests/cases/compiler/resolutionCandidateFromPackageJsonField2.ts
@@ -0,0 +1,21 @@
+// @moduleResolution: node10,bundler
+
+// @filename: tsconfig.json
+{
+    "compilerOptions": {
+        "paths": {
+            "foo/*": ["./dist/*"],
+            "baz/*.ts": ["./types/*.d.ts"]
+        }
+    }
+}
+
+// @filename: dist/bar.ts
+export const a = 1234;
+
+// @filename: types/main.d.ts
+export const b: string;
+
+// @filename: test.ts
+import { a } from "foo/bar.ts";
+import { b } from "baz/main.ts";