diff --git a/packages/utils/node-resolver-core/src/NodeResolver.js b/packages/utils/node-resolver-core/src/NodeResolver.js
index 7b7cd1b1f4c..6e38d809441 100644
--- a/packages/utils/node-resolver-core/src/NodeResolver.js
+++ b/packages/utils/node-resolver-core/src/NodeResolver.js
@@ -779,7 +779,6 @@ export default class NodeResolver {
           let res =
             (await this.loadAsFile({
               file: entry.filename,
-              asPackageEntry: true,
               extensions,
               env,
               pkg,
@@ -973,14 +972,12 @@ export default class NodeResolver {
     extensions,
     env,
     pkg,
-    asPackageEntry,
     ctx,
   }: {|
     file: string,
     extensions: Array<string>,
     env: Environment,
     pkg: InternalPackageJSON | null,
-    asPackageEntry?: boolean,
     ctx: ResolverContext,
   |}): Promise<?ResolvedFile> {
     // Try all supported extensions
@@ -1002,9 +999,12 @@ export default class NodeResolver {
     if (found) {
       return {
         path: found,
-        // If this is an entrypoint in package.json, it's possible pkg is not the
+        // If this package.json isn't a sibling of found, it's possible pkg is not the
         // closest package.json to the resolved file. Reload it instead.
-        pkg: asPackageEntry ? await this.findPackage(found, ctx) : pkg,
+        pkg:
+          pkg == null || pkg?.pkgdir !== path.basename(found)
+            ? await this.findPackage(found, ctx)
+            : pkg,
       };
     }
 
diff --git a/packages/utils/node-resolver-core/test/resolver.js b/packages/utils/node-resolver-core/test/resolver.js
index e38c4d2287b..fbe6074c704 100644
--- a/packages/utils/node-resolver-core/test/resolver.js
+++ b/packages/utils/node-resolver-core/test/resolver.js
@@ -379,6 +379,10 @@ describe('resolver', function () {
             fileName: 'package.json',
             aboveFilePath: path.join(__dirname, '..', 'src', '_empty.js'),
           },
+          {
+            fileName: 'package.json',
+            aboveFilePath: path.join(__dirname, '..', 'src', '_empty.js'),
+          },
         ],
         invalidateOnFileChange: [
           path.join(rootDir, 'package.json'),
@@ -441,6 +445,10 @@ describe('resolver', function () {
             fileName: 'node_modules/foo',
             aboveFilePath: path.join(rootDir, 'foo.js'),
           },
+          {
+            fileName: 'package.json',
+            aboveFilePath: path.join(rootDir, 'node_modules/foo/index.js'),
+          },
         ],
         invalidateOnFileChange: [
           path.join(rootDir, 'package.json'),
@@ -681,6 +689,15 @@ describe('resolver', function () {
               'main.js/package.json',
             ),
           },
+          {
+            fileName: 'package.json',
+            aboveFilePath: path.join(
+              rootDir,
+              'node_modules',
+              'package-fallback',
+              'index.js',
+            ),
+          },
         ],
         invalidateOnFileChange: [
           path.join(rootDir, 'package.json'),
@@ -749,6 +766,16 @@ describe('resolver', function () {
               'package.json',
             ),
           },
+          {
+            fileName: 'package.json',
+            aboveFilePath: path.join(
+              rootDir,
+              'node_modules',
+              'package-main-directory',
+              'nested',
+              'index.js',
+            ),
+          },
         ],
         invalidateOnFileChange: [
           path.join(rootDir, 'package.json'),
@@ -786,6 +813,16 @@ describe('resolver', function () {
             fileName: 'node_modules/foo',
             aboveFilePath: path.join(rootDir, 'foo.js'),
           },
+          {
+            fileName: 'package.json',
+            aboveFilePath: path.join(
+              rootDir,
+              'node_modules',
+              'foo',
+              'nested',
+              'baz.js',
+            ),
+          },
         ],
         invalidateOnFileChange: [
           path.join(rootDir, 'package.json'),
@@ -818,6 +855,16 @@ describe('resolver', function () {
             fileName: 'node_modules/@scope/pkg',
             aboveFilePath: path.join(rootDir, 'foo.js'),
           },
+          {
+            fileName: 'package.json',
+            aboveFilePath: path.join(
+              rootDir,
+              'node_modules',
+              '@scope',
+              'pkg',
+              'index.js',
+            ),
+          },
         ],
         invalidateOnFileChange: [
           path.join(rootDir, 'package.json'),
@@ -850,6 +897,17 @@ describe('resolver', function () {
             fileName: 'node_modules/@scope/pkg',
             aboveFilePath: path.join(rootDir, 'foo.js'),
           },
+          {
+            fileName: 'package.json',
+            aboveFilePath: path.join(
+              rootDir,
+              'node_modules',
+              '@scope',
+              'pkg',
+              'foo',
+              'bar.js',
+            ),
+          },
         ],
         invalidateOnFileChange: [
           path.join(rootDir, 'package.json'),
@@ -886,6 +944,16 @@ describe('resolver', function () {
               fileName: 'node_modules/side-effects-false',
               aboveFilePath: path.join(rootDir, 'foo.js'),
             },
+            {
+              fileName: 'package.json',
+              aboveFilePath: path.join(
+                rootDir,
+                'node_modules',
+                'side-effects-false',
+                'src',
+                'index.js',
+              ),
+            },
           ],
           invalidateOnFileChange: [
             path.join(rootDir, 'package.json'),
@@ -926,6 +994,16 @@ describe('resolver', function () {
               fileName: 'node_modules/side-effects-false',
               aboveFilePath: path.join(rootDir, 'foo.js'),
             },
+            {
+              fileName: 'package.json',
+              aboveFilePath: path.join(
+                rootDir,
+                'node_modules',
+                'side-effects-false',
+                'src',
+                'index.js',
+              ),
+            },
           ],
           invalidateOnFileChange: [
             path.join(rootDir, 'package.json'),
@@ -985,6 +1063,16 @@ describe('resolver', function () {
               ),
               fileName: 'package.json',
             },
+            {
+              aboveFilePath: path.join(
+                rootDir,
+                'node_modules',
+                'side-effects-false',
+                'src',
+                'index.js',
+              ),
+              fileName: 'package.json',
+            },
           ],
           invalidateOnFileChange: [
             path.join(rootDir, 'package.json'),
@@ -1044,6 +1132,16 @@ describe('resolver', function () {
               ),
               fileName: 'package.json',
             },
+            {
+              aboveFilePath: path.join(
+                rootDir,
+                'node_modules',
+                'side-effects-false',
+                'src',
+                'index.js',
+              ),
+              fileName: 'package.json',
+            },
           ],
           invalidateOnFileChange: [
             path.join(rootDir, 'package.json'),
@@ -1461,6 +1559,15 @@ describe('resolver', function () {
             fileName: 'node_modules/package-browser-alias',
             aboveFilePath: path.join(rootDir, 'foo.js'),
           },
+          {
+            fileName: 'package.json',
+            aboveFilePath: path.join(
+              rootDir,
+              'node_modules',
+              'package-browser-alias',
+              'bar.js',
+            ),
+          },
         ],
         invalidateOnFileChange: [
           path.join(rootDir, 'package.json'),
@@ -1518,6 +1625,15 @@ describe('resolver', function () {
               'bar',
             ),
           },
+          {
+            fileName: 'package.json',
+            aboveFilePath: path.join(
+              rootDir,
+              'node_modules',
+              'package-browser-alias',
+              'bar.js',
+            ),
+          },
         ],
         invalidateOnFileChange: [
           path.join(rootDir, 'package.json'),
@@ -1560,6 +1676,14 @@ describe('resolver', function () {
             fileName: 'node_modules/package-browser-alias',
             aboveFilePath: path.join(rootDir, 'foo.js'),
           },
+          {
+            fileName: 'package.json',
+            aboveFilePath: path.join(
+              rootDir,
+              'node_modules/package-browser-alias',
+              'foo.js',
+            ),
+          },
         ],
         invalidateOnFileChange: [
           path.join(rootDir, 'package.json'),
@@ -1617,6 +1741,17 @@ describe('resolver', function () {
               'nested',
             ),
           },
+          {
+            fileName: 'package.json',
+            aboveFilePath: path.join(
+              rootDir,
+              'node_modules',
+              'package-browser-alias',
+              'subfolder1',
+              'subfolder2',
+              'subfile.js',
+            ),
+          },
         ],
         invalidateOnFileChange: [
           path.join(rootDir, 'package.json'),
@@ -1654,6 +1789,15 @@ describe('resolver', function () {
             fileName: 'node_modules/package-alias',
             aboveFilePath: path.join(rootDir, 'foo.js'),
           },
+          {
+            fileName: 'package.json',
+            aboveFilePath: path.join(
+              rootDir,
+              'node_modules',
+              'package-alias',
+              'bar.js',
+            ),
+          },
         ],
         invalidateOnFileChange: [
           path.join(rootDir, 'package.json'),
@@ -1701,6 +1845,15 @@ describe('resolver', function () {
               'bar',
             ),
           },
+          {
+            fileName: 'package.json',
+            aboveFilePath: path.join(
+              rootDir,
+              'node_modules',
+              'package-alias',
+              'bar.js',
+            ),
+          },
         ],
         invalidateOnFileChange: [
           path.join(rootDir, 'package.json'),
@@ -1755,6 +1908,16 @@ describe('resolver', function () {
               'test',
             ),
           },
+          {
+            fileName: 'package.json',
+            aboveFilePath: path.join(
+              rootDir,
+              'node_modules',
+              'package-alias-glob',
+              'src',
+              'test.js',
+            ),
+          },
         ],
         invalidateOnFileChange: [
           path.join(rootDir, 'package.json'),
@@ -1792,6 +1955,15 @@ describe('resolver', function () {
             fileName: 'node_modules/foo',
             aboveFilePath: path.join(rootDir, 'foo.js'),
           },
+          {
+            fileName: 'package.json',
+            aboveFilePath: path.join(
+              rootDir,
+              'node_modules',
+              'foo',
+              'index.js',
+            ),
+          },
         ],
         invalidateOnFileChange: [
           path.join(rootDir, 'package.json'),
@@ -1834,6 +2006,10 @@ describe('resolver', function () {
               'foo.js',
             ),
           },
+          {
+            fileName: 'package.json',
+            aboveFilePath: path.join(rootDir, 'node_modules', 'foo/index.js'),
+          },
         ],
         invalidateOnFileChange: [
           path.join(rootDir, 'package.json'),
@@ -1877,6 +2053,10 @@ describe('resolver', function () {
               'foo.js',
             ),
           },
+          {
+            fileName: 'package.json',
+            aboveFilePath: path.join(rootDir, 'node_modules', 'foo', 'bar.js'),
+          },
         ],
         invalidateOnFileChange: [
           path.join(rootDir, 'package.json'),
@@ -1910,6 +2090,10 @@ describe('resolver', function () {
             fileName: 'package.json',
             aboveFilePath: path.join(rootDir, 'bar.js'),
           },
+          {
+            fileName: 'package.json',
+            aboveFilePath: path.join(rootDir, 'bar.js'),
+          },
         ],
         invalidateOnFileChange: [path.join(rootDir, 'package.json')],
       });
@@ -1944,6 +2128,10 @@ describe('resolver', function () {
             fileName: 'package.json',
             aboveFilePath: path.join(rootDir, 'bar.js'),
           },
+          {
+            fileName: 'package.json',
+            aboveFilePath: path.join(rootDir, 'bar.js'),
+          },
         ],
         invalidateOnFileChange: [
           path.join(rootDir, 'package.json'),
@@ -1976,6 +2164,10 @@ describe('resolver', function () {
             fileName: 'package.json',
             aboveFilePath: path.join(rootDir, 'nested', 'test.js'),
           },
+          {
+            fileName: 'package.json',
+            aboveFilePath: path.join(rootDir, 'nested', 'test.js'),
+          },
         ],
         invalidateOnFileChange: [path.join(rootDir, 'package.json')],
       });
@@ -2014,6 +2206,10 @@ describe('resolver', function () {
           {
             filePath: path.join(rootDir, 'nested', 'package.json'),
           },
+          {
+            fileName: 'package.json',
+            aboveFilePath: path.join(rootDir, 'nested/index.js'),
+          },
         ],
         invalidateOnFileChange: [path.join(rootDir, 'package.json')],
       });
@@ -2043,6 +2239,10 @@ describe('resolver', function () {
             fileName: 'package.json',
             aboveFilePath: path.join(rootDir, 'nested', 'test.js'),
           },
+          {
+            fileName: 'package.json',
+            aboveFilePath: path.join(rootDir, 'nested', 'test.js'),
+          },
         ],
         invalidateOnFileChange: [path.join(rootDir, 'package.json')],
       });
@@ -2081,6 +2281,10 @@ describe('resolver', function () {
           {
             filePath: path.join(rootDir, 'nested', 'package.json'),
           },
+          {
+            fileName: 'package.json',
+            aboveFilePath: path.join(rootDir, 'nested/index.js'),
+          },
         ],
         invalidateOnFileChange: [path.join(rootDir, 'package.json')],
       });
@@ -2110,6 +2314,10 @@ describe('resolver', function () {
             fileName: 'package.json',
             aboveFilePath: path.join(rootDir, 'bar.js'),
           },
+          {
+            fileName: 'package.json',
+            aboveFilePath: path.join(rootDir, 'bar.js'),
+          },
         ],
         invalidateOnFileChange: [path.join(rootDir, 'package.json')],
       });
@@ -2139,6 +2347,10 @@ describe('resolver', function () {
             fileName: 'package.json',
             aboveFilePath: path.join(rootDir, 'nested', 'test'),
           },
+          {
+            fileName: 'package.json',
+            aboveFilePath: path.join(rootDir, 'nested', 'test.js'),
+          },
         ],
         invalidateOnFileChange: [path.join(rootDir, 'package.json')],
       });
@@ -2168,6 +2380,10 @@ describe('resolver', function () {
             fileName: 'package.json',
             aboveFilePath: path.join(rootDir, 'nested', 'test.js'),
           },
+          {
+            fileName: 'package.json',
+            aboveFilePath: path.join(rootDir, 'nested', 'test.js'),
+          },
         ],
         invalidateOnFileChange: [path.join(rootDir, 'package.json')],
       });
@@ -2202,6 +2418,10 @@ describe('resolver', function () {
             fileName: 'package.json',
             aboveFilePath: path.join(rootDir, 'nested', 'test.js'),
           },
+          {
+            fileName: 'package.json',
+            aboveFilePath: path.join(rootDir, 'nested', 'test.js'),
+          },
         ],
         invalidateOnFileChange: [
           path.join(rootDir, 'package.json'),