diff --git a/packages/playground/define/__tests__/define.spec.ts b/packages/playground/define/__tests__/define.spec.ts
index f5eb78ea4e2766..f417026ebd186d 100644
--- a/packages/playground/define/__tests__/define.spec.ts
+++ b/packages/playground/define/__tests__/define.spec.ts
@@ -20,4 +20,13 @@ test('string', async () => {
   expect(await page.textContent('.spread-array')).toBe(
     JSON.stringify([...defines.__STRING__])
   )
+  expect(await page.textContent('.import-file')).not.toBe(
+    `import * from "${defines.__IMPORT_FILE_NAME__}"`
+  )
+  expect(await page.textContent('.export-file')).not.toBe(
+    `export * from "${defines.__EXPORT_FILE_NAME__}"`
+  )
+  expect(await page.textContent('.path')).not.toBe(
+    `import * from "xxxx/${defines.PATH}"`
+  )
 })
diff --git a/packages/playground/define/index.html b/packages/playground/define/index.html
index bf6a9c59689396..a285764dd9e0b4 100644
--- a/packages/playground/define/index.html
+++ b/packages/playground/define/index.html
@@ -9,6 +9,9 @@ <h1>Define</h1>
 <p>process as property: <code class="process-as-property"></code></p>
 <p>spread object: <code class="spread-object"></code></p>
 <p>spread array: <code class="spread-array"></code></p>
+<p>import file: <code class="import-file"></code></p>
+<p>export file: <code class="export-file"></code></p>
+<p>path: <code class="path"></code></p>
 
 <script type="module">
   const __VAR_NAME__ = true // ensure define doesn't replace var name
@@ -26,6 +29,9 @@ <h1>Define</h1>
     })
   )
   text('.spread-array', JSON.stringify([...`"${__STRING__}"`]))
+  text('.import-file', `import * from "__IMPORT_FILE_NAME__"`)
+  text('.export-file', `export * from "__EXPORT_FILE_NAME__"`)
+  text('.path', `import * from "xxxx/PATH"`)
 
   function text(el, text) {
     document.querySelector(el).textContent = text
diff --git a/packages/playground/define/vite.config.js b/packages/playground/define/vite.config.js
index 848abd09322df6..7f6c914b3062f1 100644
--- a/packages/playground/define/vite.config.js
+++ b/packages/playground/define/vite.config.js
@@ -16,6 +16,9 @@ module.exports = {
       }
     },
     __VAR_NAME__: false,
-    'process.env.SOMEVAR': '"SOMEVAR"'
+    'process.env.SOMEVAR': '"SOMEVAR"',
+    __IMPORT_FILE_NAME__: '"importFileName"',
+    __EXPORT_FILE_NAME__: '"exportFileName"',
+    PATH: '"filePath"'
   }
 }
diff --git a/packages/vite/src/node/plugins/define.ts b/packages/vite/src/node/plugins/define.ts
index 187cacf54ab1c8..7d10035a0d51d0 100644
--- a/packages/vite/src/node/plugins/define.ts
+++ b/packages/vite/src/node/plugins/define.ts
@@ -53,7 +53,6 @@ export function definePlugin(config: ResolvedConfig): Plugin {
         'globalThis.process.env.': `({}).`
       })
     }
-
     const replacements: Record<string, string> = {
       ...(isNeedProcessEnv ? processNodeEnv : {}),
       ...userDefine,
@@ -62,20 +61,30 @@ export function definePlugin(config: ResolvedConfig): Plugin {
     }
 
     const replacementsKeys = Object.keys(replacements)
-    const pattern = replacementsKeys.length
-      ? new RegExp(
-          // Do not allow preceding '.', but do allow preceding '...' for spread operations
-          '(?<!(?<!\\.\\.)\\.)\\b(' +
-            replacementsKeys
-              .map((str) => {
-                return str.replace(/[-[\]/{}()*+?.\\^$|]/g, '\\$&')
-              })
-              .join('|') +
-            // prevent trailing assignments
-            ')\\b(?!\\s*?=[^=])',
-          'g'
-        )
-      : null
+
+    if (!replacementsKeys.length) {
+      return [replacements, null]
+    }
+
+    const replacementsStr = replacementsKeys
+      .map((str) => {
+        return str.replace(/[-[\]/{}()*+?.\\^$|]/g, '\\$&')
+      })
+      .join('|')
+
+    // The following characters are not allowed because they are String boundaries
+    const characters = '[\'"`\\/-_]'
+
+    const pattern = new RegExp(
+      `(?<!${characters})` +
+        // Do not allow preceding '.', but do allow preceding '...' for spread operations
+        '(?<!(?<!\\.\\.)\\.)' +
+        `\\b(${replacementsStr})\\b` +
+        `(?!${characters})` +
+        // prevent trailing assignments
+        '(?!\\s*?=[^=])',
+      'g'
+    )
 
     return [replacements, pattern]
   }