diff --git a/packages/vite/src/node/__tests__/environment.spec.ts b/packages/vite/src/node/__tests__/environment.spec.ts
index 6cd24a2ece3c0b..96a2964ea9b8e4 100644
--- a/packages/vite/src/node/__tests__/environment.spec.ts
+++ b/packages/vite/src/node/__tests__/environment.spec.ts
@@ -7,7 +7,11 @@ import { createBuilder } from '../build'
 import { createServerModuleRunner } from '../ssr/runtime/serverModuleRunner'
 
 describe('custom environment conditions', () => {
-  function getConfig(): InlineConfig {
+  function getConfig({
+    noExternal,
+  }: {
+    noExternal: true | undefined
+  }): InlineConfig {
     return {
       configFile: false,
       root: import.meta.dirname,
@@ -19,7 +23,7 @@ describe('custom environment conditions', () => {
         // no web / default
         ssr: {
           resolve: {
-            noExternal: true,
+            noExternal,
           },
           build: {
             outDir: path.join(
@@ -35,8 +39,9 @@ describe('custom environment conditions', () => {
         worker: {
           webCompatible: true,
           resolve: {
-            noExternal: true,
+            noExternal,
             conditions: ['worker'],
+            externalConditions: ['worker'],
           },
           build: {
             outDir: path.join(
@@ -52,8 +57,9 @@ describe('custom environment conditions', () => {
         custom1: {
           webCompatible: true,
           resolve: {
-            noExternal: true,
+            noExternal,
             conditions: ['custom1'],
+            externalConditions: ['custom1'],
           },
           build: {
             outDir: path.join(
@@ -69,8 +75,9 @@ describe('custom environment conditions', () => {
         custom2: {
           webCompatible: false,
           resolve: {
-            noExternal: true,
+            noExternal,
             conditions: ['custom2'],
+            externalConditions: ['custom2'],
           },
           build: {
             outDir: path.join(
@@ -86,8 +93,9 @@ describe('custom environment conditions', () => {
         custom3: {
           webCompatible: false,
           resolve: {
-            noExternal: true,
+            noExternal,
             conditions: ['custom3'],
+            externalConditions: ['custom3'],
           },
           build: {
             outDir: path.join(
@@ -103,8 +111,9 @@ describe('custom environment conditions', () => {
         custom3_2: {
           webCompatible: false,
           resolve: {
-            noExternal: true,
+            noExternal,
             conditions: ['custom3'],
+            externalConditions: ['custom3'],
           },
           build: {
             outDir: path.join(
@@ -120,8 +129,8 @@ describe('custom environment conditions', () => {
     }
   }
 
-  test('dev', async () => {
-    const server = await createServer(getConfig())
+  test('dev noExternal', async () => {
+    const server = await createServer(getConfig({ noExternal: true }))
     onTestFinished(() => server.close())
 
     const results: Record<string, unknown> = {}
@@ -154,8 +163,44 @@ describe('custom environment conditions', () => {
     `)
   })
 
+  test('dev external', async () => {
+    const server = await createServer(getConfig({ noExternal: undefined }))
+    onTestFinished(() => server.close())
+
+    const results: Record<string, unknown> = {}
+    for (const key of [
+      'ssr',
+      'worker',
+      'custom1',
+      'custom2',
+      'custom3',
+      'custom3_2',
+    ]) {
+      const runner = createServerModuleRunner(server.environments[key], {
+        hmr: {
+          logger: false,
+        },
+        sourcemapInterceptor: false,
+      })
+      const mod = await runner.import(
+        '/fixtures/test-dep-conditions-app/entry.js',
+      )
+      results[key] = mod.default
+    }
+    expect(results).toMatchInlineSnapshot(`
+      {
+        "custom1": "index.custom1.js",
+        "custom2": "index.custom2.js",
+        "custom3": "index.custom3.js",
+        "custom3_2": "index.custom3.js",
+        "ssr": "index.default.js",
+        "worker": "index.worker.js",
+      }
+    `)
+  })
+
   test('css', async () => {
-    const server = await createServer(getConfig())
+    const server = await createServer(getConfig({ noExternal: true }))
     onTestFinished(() => server.close())
 
     const modJs = await server.ssrLoadModule(
@@ -174,7 +219,7 @@ describe('custom environment conditions', () => {
   })
 
   test('build', async () => {
-    const builder = await createBuilder(getConfig())
+    const builder = await createBuilder(getConfig({ noExternal: true }))
     const results: Record<string, unknown> = {}
     for (const key of [
       'ssr',
diff --git a/packages/vite/src/node/packages.ts b/packages/vite/src/node/packages.ts
index 175505d49e5373..ffabe43f89595a 100644
--- a/packages/vite/src/node/packages.ts
+++ b/packages/vite/src/node/packages.ts
@@ -9,7 +9,7 @@ import {
   tryStatSync,
 } from './utils'
 import type { Plugin } from './plugin'
-import type { InternalResolveOptions } from './plugins/resolve'
+import type { InternalResolveOptionsWithOverrideConditions } from './plugins/resolve'
 
 let pnp: typeof import('pnpapi') | undefined
 if (process.versions.pnp) {
@@ -27,11 +27,11 @@ export interface PackageData {
   setResolvedCache: (
     key: string,
     entry: string,
-    options: InternalResolveOptions,
+    options: InternalResolveOptionsWithOverrideConditions,
   ) => void
   getResolvedCache: (
     key: string,
-    options: InternalResolveOptions,
+    options: InternalResolveOptionsWithOverrideConditions,
   ) => string | undefined
   data: {
     [field: string]: any
@@ -223,7 +223,10 @@ export function loadPackageData(pkgPath: string): PackageData {
   return pkg
 }
 
-function getResolveCacheKey(key: string, options: InternalResolveOptions) {
+function getResolveCacheKey(
+  key: string,
+  options: InternalResolveOptionsWithOverrideConditions,
+) {
   // cache key needs to include options which affect
   // `resolvePackageEntry` or `resolveDeepImport`
   return [
@@ -231,6 +234,7 @@ function getResolveCacheKey(key: string, options: InternalResolveOptions) {
     options.webCompatible ? '1' : '0',
     options.isRequire ? '1' : '0',
     options.conditions.join('_'),
+    options.overrideConditions?.join('_') || '',
     options.extensions.join('_'),
     options.mainFields.join('_'),
   ].join('|')