diff --git a/src/compiler/moduleNameResolver.ts b/src/compiler/moduleNameResolver.ts
index 8bb65e57616d5..510fc096297a7 100644
--- a/src/compiler/moduleNameResolver.ts
+++ b/src/compiler/moduleNameResolver.ts
@@ -1012,8 +1012,10 @@ namespace ts {
                 }
                 else {
                     const jsPath = tryReadPackageJsonFields(/*readTypes*/ false, packageJsonContent, nodeModuleDirectory, state);
-                    if (typeof jsPath === "string") {
-                        subModuleName = removeExtension(removeExtension(jsPath.substring(nodeModuleDirectory.length + 1), Extension.Js), Extension.Jsx) + Extension.Dts;
+                    if (typeof jsPath === "string" && jsPath.length > nodeModuleDirectory.length) {
+                        const potentialSubModule = jsPath.substring(nodeModuleDirectory.length + 1);
+                        subModuleName = (forEach(supportedJavascriptExtensions, extension =>
+                            tryRemoveExtension(potentialSubModule, extension)) || potentialSubModule) + Extension.Dts;
                     }
                     else {
                         subModuleName = "index.d.ts";
@@ -1047,9 +1049,18 @@ namespace ts {
     }
 
     function loadModuleFromPackageJson(jsonContent: PackageJsonPathFields, extensions: Extensions, candidate: string, failedLookupLocations: Push<string>, state: ModuleResolutionState): PathAndExtension | undefined {
-        const file = tryReadPackageJsonFields(extensions !== Extensions.JavaScript && extensions !== Extensions.Json, jsonContent, candidate, state);
+        let file = tryReadPackageJsonFields(extensions !== Extensions.JavaScript && extensions !== Extensions.Json, jsonContent, candidate, state);
         if (!file) {
-            return undefined;
+            if (extensions === Extensions.TypeScript) {
+                // When resolving typescript modules, try resolving using main field as well
+                file = tryReadPackageJsonFields(/*readTypes*/ false, jsonContent, candidate, state);
+                if (!file) {
+                    return undefined;
+                }
+            }
+            else {
+                return undefined;
+            }
         }
 
         const onlyRecordFailures = !directoryProbablyExists(getDirectoryPath(file), state.host);
diff --git a/src/harness/unittests/moduleResolution.ts b/src/harness/unittests/moduleResolution.ts
index fc1811420d34b..b5c527aa246df 100644
--- a/src/harness/unittests/moduleResolution.ts
+++ b/src/harness/unittests/moduleResolution.ts
@@ -181,6 +181,13 @@ namespace ts {
                     "/a/b/foo.ts",
                     "/a/b/foo.tsx",
                     "/a/b/foo.d.ts",
+                    "/c/d",
+                    "/c/d.ts",
+                    "/c/d.tsx",
+                    "/c/d.d.ts",
+                    "/c/d/index.ts",
+                    "/c/d/index.tsx",
+                    "/c/d/index.d.ts",
                     "/a/b/foo/index.ts",
                     "/a/b/foo/index.tsx",
                 ]);
diff --git a/tests/baselines/reference/duplicatePackage_relativeImportWithinPackage.trace.json b/tests/baselines/reference/duplicatePackage_relativeImportWithinPackage.trace.json
index d592022e2e177..d75683d210f83 100644
--- a/tests/baselines/reference/duplicatePackage_relativeImportWithinPackage.trace.json
+++ b/tests/baselines/reference/duplicatePackage_relativeImportWithinPackage.trace.json
@@ -40,6 +40,7 @@
     "File '/node_modules/a/node_modules/foo.d.ts' does not exist.",
     "'package.json' does not have a 'typings' field.",
     "'package.json' does not have a 'types' field.",
+    "'package.json' does not have a 'main' field.",
     "File '/node_modules/a/node_modules/foo/index.ts' does not exist.",
     "File '/node_modules/a/node_modules/foo/index.tsx' does not exist.",
     "File '/node_modules/a/node_modules/foo/index.d.ts' exist - use it as a name resolution result.",
diff --git a/tests/baselines/reference/duplicatePackage_relativeImportWithinPackage_scoped.trace.json b/tests/baselines/reference/duplicatePackage_relativeImportWithinPackage_scoped.trace.json
index 108873d70f900..7b07ecd66e49d 100644
--- a/tests/baselines/reference/duplicatePackage_relativeImportWithinPackage_scoped.trace.json
+++ b/tests/baselines/reference/duplicatePackage_relativeImportWithinPackage_scoped.trace.json
@@ -40,6 +40,7 @@
     "File '/node_modules/a/node_modules/@foo/bar.d.ts' does not exist.",
     "'package.json' does not have a 'typings' field.",
     "'package.json' does not have a 'types' field.",
+    "'package.json' does not have a 'main' field.",
     "File '/node_modules/a/node_modules/@foo/bar/index.ts' does not exist.",
     "File '/node_modules/a/node_modules/@foo/bar/index.tsx' does not exist.",
     "File '/node_modules/a/node_modules/@foo/bar/index.d.ts' exist - use it as a name resolution result.",
diff --git a/tests/baselines/reference/moduleResolutionWithExtensions_unexpected.trace.json b/tests/baselines/reference/moduleResolutionWithExtensions_unexpected.trace.json
index 5f32a4bf511ef..60cdab44a29fc 100644
--- a/tests/baselines/reference/moduleResolutionWithExtensions_unexpected.trace.json
+++ b/tests/baselines/reference/moduleResolutionWithExtensions_unexpected.trace.json
@@ -11,6 +11,14 @@
     "File '/node_modules/normalize.css.d.ts' does not exist.",
     "'package.json' does not have a 'typings' field.",
     "'package.json' does not have a 'types' field.",
+    "'package.json' has 'main' field 'normalize.css' that references '/node_modules/normalize.css/normalize.css'.",
+    "File '/node_modules/normalize.css/normalize.css' exist - use it as a name resolution result.",
+    "File '/node_modules/normalize.css/normalize.css' has an unsupported extension, so skipping it.",
+    "Loading module as file / folder, candidate module location '/node_modules/normalize.css/normalize.css', target file type 'TypeScript'.",
+    "File '/node_modules/normalize.css/normalize.css.ts' does not exist.",
+    "File '/node_modules/normalize.css/normalize.css.tsx' does not exist.",
+    "File '/node_modules/normalize.css/normalize.css.d.ts' does not exist.",
+    "Directory '/node_modules/normalize.css/normalize.css' does not exist, skipping all lookups in it.",
     "File '/node_modules/normalize.css/index.ts' does not exist.",
     "File '/node_modules/normalize.css/index.tsx' does not exist.",
     "File '/node_modules/normalize.css/index.d.ts' does not exist.",
diff --git a/tests/baselines/reference/moduleResolution_packageJson_yesAtPackageRoot_mainFieldInSubDirectory.js b/tests/baselines/reference/moduleResolution_packageJson_yesAtPackageRoot_mainFieldInSubDirectory.js
new file mode 100644
index 0000000000000..1aa0a624d8dbc
--- /dev/null
+++ b/tests/baselines/reference/moduleResolution_packageJson_yesAtPackageRoot_mainFieldInSubDirectory.js
@@ -0,0 +1,15 @@
+//// [tests/cases/compiler/moduleResolution_packageJson_yesAtPackageRoot_mainFieldInSubDirectory.ts] ////
+
+//// [package.json]
+{ "name": "foo", "version": "1.2.3", "main": "src/index.js" }
+
+//// [index.d.ts]
+export const x: number;
+
+//// [index.ts]
+import { x } from "foo";
+
+
+//// [index.js]
+"use strict";
+exports.__esModule = true;
diff --git a/tests/baselines/reference/moduleResolution_packageJson_yesAtPackageRoot_mainFieldInSubDirectory.symbols b/tests/baselines/reference/moduleResolution_packageJson_yesAtPackageRoot_mainFieldInSubDirectory.symbols
new file mode 100644
index 0000000000000..7a5c1d7ea2788
--- /dev/null
+++ b/tests/baselines/reference/moduleResolution_packageJson_yesAtPackageRoot_mainFieldInSubDirectory.symbols
@@ -0,0 +1,8 @@
+=== /node_modules/foo/src/index.d.ts ===
+export const x: number;
+>x : Symbol(x, Decl(index.d.ts, 0, 12))
+
+=== /index.ts ===
+import { x } from "foo";
+>x : Symbol(x, Decl(index.ts, 0, 8))
+
diff --git a/tests/baselines/reference/moduleResolution_packageJson_yesAtPackageRoot_mainFieldInSubDirectory.trace.json b/tests/baselines/reference/moduleResolution_packageJson_yesAtPackageRoot_mainFieldInSubDirectory.trace.json
new file mode 100644
index 0000000000000..849b65ee59ff6
--- /dev/null
+++ b/tests/baselines/reference/moduleResolution_packageJson_yesAtPackageRoot_mainFieldInSubDirectory.trace.json
@@ -0,0 +1,26 @@
+[
+    "======== Resolving module 'foo' from '/index.ts'. ========",
+    "Module resolution kind is not specified, using 'NodeJs'.",
+    "Loading module 'foo' from 'node_modules' folder, target file type 'TypeScript'.",
+    "'package.json' does not have a 'typings' field.",
+    "'package.json' does not have a 'types' field.",
+    "'package.json' has 'main' field 'src/index.js' that references '/node_modules/foo/src/index.js'.",
+    "Found 'package.json' at '/node_modules/foo/package.json'. Package ID is 'foo/src/index.d.ts@1.2.3'.",
+    "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 'typings' field.",
+    "'package.json' does not have a 'types' field.",
+    "'package.json' has 'main' field 'src/index.js' that references '/node_modules/foo/src/index.js'.",
+    "File '/node_modules/foo/src/index.js' does not exist.",
+    "Loading module as file / folder, candidate module location '/node_modules/foo/src/index.js', target file type 'TypeScript'.",
+    "File '/node_modules/foo/src/index.js.ts' does not exist.",
+    "File '/node_modules/foo/src/index.js.tsx' does not exist.",
+    "File '/node_modules/foo/src/index.js.d.ts' does not exist.",
+    "File name '/node_modules/foo/src/index.js' has a '.js' extension - stripping it.",
+    "File '/node_modules/foo/src/index.ts' does not exist.",
+    "File '/node_modules/foo/src/index.tsx' does not exist.",
+    "File '/node_modules/foo/src/index.d.ts' exist - use it as a name resolution result.",
+    "Resolving real path for '/node_modules/foo/src/index.d.ts', result '/node_modules/foo/src/index.d.ts'.",
+    "======== Module name 'foo' was successfully resolved to '/node_modules/foo/src/index.d.ts'. ========"
+]
\ No newline at end of file
diff --git a/tests/baselines/reference/moduleResolution_packageJson_yesAtPackageRoot_mainFieldInSubDirectory.types b/tests/baselines/reference/moduleResolution_packageJson_yesAtPackageRoot_mainFieldInSubDirectory.types
new file mode 100644
index 0000000000000..e0ae051e59f17
--- /dev/null
+++ b/tests/baselines/reference/moduleResolution_packageJson_yesAtPackageRoot_mainFieldInSubDirectory.types
@@ -0,0 +1,8 @@
+=== /node_modules/foo/src/index.d.ts ===
+export const x: number;
+>x : number
+
+=== /index.ts ===
+import { x } from "foo";
+>x : number
+
diff --git a/tests/baselines/reference/packageJsonMain.trace.json b/tests/baselines/reference/packageJsonMain.trace.json
index 6d39b9d4a7b7a..06c8cff66431b 100644
--- a/tests/baselines/reference/packageJsonMain.trace.json
+++ b/tests/baselines/reference/packageJsonMain.trace.json
@@ -11,6 +11,13 @@
     "File '/node_modules/foo.d.ts' does not exist.",
     "'package.json' does not have a 'typings' field.",
     "'package.json' does not have a 'types' field.",
+    "'package.json' has 'main' field 'oof' that references '/node_modules/foo/oof'.",
+    "File '/node_modules/foo/oof' does not exist.",
+    "Loading module as file / folder, candidate module location '/node_modules/foo/oof', target file type 'TypeScript'.",
+    "File '/node_modules/foo/oof.ts' does not exist.",
+    "File '/node_modules/foo/oof.tsx' does not exist.",
+    "File '/node_modules/foo/oof.d.ts' does not exist.",
+    "Directory '/node_modules/foo/oof' does not exist, skipping all lookups in it.",
     "File '/node_modules/foo/index.ts' does not exist.",
     "File '/node_modules/foo/index.tsx' does not exist.",
     "File '/node_modules/foo/index.d.ts' does not exist.",
@@ -40,6 +47,18 @@
     "File '/node_modules/bar.d.ts' does not exist.",
     "'package.json' does not have a 'typings' field.",
     "'package.json' does not have a 'types' field.",
+    "'package.json' has 'main' field 'rab.js' that references '/node_modules/bar/rab.js'.",
+    "File '/node_modules/bar/rab.js' exist - use it as a name resolution result.",
+    "File '/node_modules/bar/rab.js' has an unsupported extension, so skipping it.",
+    "Loading module as file / folder, candidate module location '/node_modules/bar/rab.js', target file type 'TypeScript'.",
+    "File '/node_modules/bar/rab.js.ts' does not exist.",
+    "File '/node_modules/bar/rab.js.tsx' does not exist.",
+    "File '/node_modules/bar/rab.js.d.ts' does not exist.",
+    "File name '/node_modules/bar/rab.js' has a '.js' extension - stripping it.",
+    "File '/node_modules/bar/rab.ts' does not exist.",
+    "File '/node_modules/bar/rab.tsx' does not exist.",
+    "File '/node_modules/bar/rab.d.ts' does not exist.",
+    "Directory '/node_modules/bar/rab.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.",
@@ -67,6 +86,15 @@
     "File '/node_modules/baz.d.ts' does not exist.",
     "'package.json' does not have a 'typings' field.",
     "'package.json' does not have a 'types' field.",
+    "'package.json' has 'main' field 'zab' that references '/node_modules/baz/zab'.",
+    "File '/node_modules/baz/zab' does not exist.",
+    "Loading module as file / folder, candidate module location '/node_modules/baz/zab', target file type 'TypeScript'.",
+    "File '/node_modules/baz/zab.ts' does not exist.",
+    "File '/node_modules/baz/zab.tsx' does not exist.",
+    "File '/node_modules/baz/zab.d.ts' does not exist.",
+    "File '/node_modules/baz/zab/index.ts' does not exist.",
+    "File '/node_modules/baz/zab/index.tsx' does not exist.",
+    "File '/node_modules/baz/zab/index.d.ts' does not exist.",
     "File '/node_modules/baz/index.ts' does not exist.",
     "File '/node_modules/baz/index.tsx' does not exist.",
     "File '/node_modules/baz/index.d.ts' does not exist.",
diff --git a/tests/baselines/reference/packageJsonMain_isNonRecursive.trace.json b/tests/baselines/reference/packageJsonMain_isNonRecursive.trace.json
index 81f5be11a6d76..a2878a2a4fed5 100644
--- a/tests/baselines/reference/packageJsonMain_isNonRecursive.trace.json
+++ b/tests/baselines/reference/packageJsonMain_isNonRecursive.trace.json
@@ -11,6 +11,15 @@
     "File '/node_modules/foo.d.ts' does not exist.",
     "'package.json' does not have a 'typings' field.",
     "'package.json' does not have a 'types' field.",
+    "'package.json' has 'main' field 'oof' that references '/node_modules/foo/oof'.",
+    "File '/node_modules/foo/oof' does not exist.",
+    "Loading module as file / folder, candidate module location '/node_modules/foo/oof', target file type 'TypeScript'.",
+    "File '/node_modules/foo/oof.ts' does not exist.",
+    "File '/node_modules/foo/oof.tsx' does not exist.",
+    "File '/node_modules/foo/oof.d.ts' does not exist.",
+    "File '/node_modules/foo/oof/index.ts' does not exist.",
+    "File '/node_modules/foo/oof/index.tsx' does not exist.",
+    "File '/node_modules/foo/oof/index.d.ts' does not exist.",
     "File '/node_modules/foo/index.ts' does not exist.",
     "File '/node_modules/foo/index.tsx' does not exist.",
     "File '/node_modules/foo/index.d.ts' does not exist.",
diff --git a/tests/cases/compiler/moduleResolution_packageJson_yesAtPackageRoot_mainFieldInSubDirectory.ts b/tests/cases/compiler/moduleResolution_packageJson_yesAtPackageRoot_mainFieldInSubDirectory.ts
new file mode 100644
index 0000000000000..4af56e48e1c3e
--- /dev/null
+++ b/tests/cases/compiler/moduleResolution_packageJson_yesAtPackageRoot_mainFieldInSubDirectory.ts
@@ -0,0 +1,10 @@
+// @traceResolution: true
+
+// @Filename: /node_modules/foo/package.json
+{ "name": "foo", "version": "1.2.3", "main": "src/index.js" }
+
+// @Filename: /node_modules/foo/src/index.d.ts
+export const x: number;
+
+// @Filename: /index.ts
+import { x } from "foo";