diff --git a/packages/payload/src/uploads/generateFileData.ts b/packages/payload/src/uploads/generateFileData.ts
index bf5c86d7f00..2f51f8e9f42 100644
--- a/packages/payload/src/uploads/generateFileData.ts
+++ b/packages/payload/src/uploads/generateFileData.ts
@@ -241,7 +241,7 @@ export const generateFileData = async <T>({
       })
 
       // Apply resize after cropping to ensure it conforms to resizeOptions
-      if (resizeOptions) {
+      if (resizeOptions && !resizeOptions.withoutEnlargement) {
         const resizedAfterCrop = await sharp(croppedImage)
           .resize({
             fit: resizeOptions?.fit || 'cover',
diff --git a/test/uploads/config.ts b/test/uploads/config.ts
index 7607f3dca9b..3c1d7e5f208 100644
--- a/test/uploads/config.ts
+++ b/test/uploads/config.ts
@@ -30,6 +30,7 @@ import {
   relationSlug,
   unstoredMediaSlug,
   versionSlug,
+  withoutEnlargeSlug,
 } from './shared.js'
 const filename = fileURLToPath(import.meta.url)
 const dirname = path.dirname(filename)
@@ -490,6 +491,19 @@ export default buildConfigWithDefaults({
         staticDir: path.resolve(dirname, './media/enlarge'),
       },
     },
+    {
+      slug: withoutEnlargeSlug,
+      fields: [],
+      upload: {
+        resizeOptions: {
+          width: 1000,
+          height: undefined,
+          fit: 'inside',
+          withoutEnlargement: true,
+        },
+        staticDir: path.resolve(dirname, './media/without-enlarge'),
+      },
+    },
     {
       slug: reduceSlug,
       fields: [],
diff --git a/test/uploads/e2e.spec.ts b/test/uploads/e2e.spec.ts
index dce24b8b1cd..5ec5aa1c430 100644
--- a/test/uploads/e2e.spec.ts
+++ b/test/uploads/e2e.spec.ts
@@ -38,6 +38,7 @@ import {
   relationSlug,
   withMetadataSlug,
   withOnlyJPEGMetadataSlug,
+  withoutEnlargeSlug,
   withoutMetadataSlug,
 } from './shared.js'
 import { startMockCorsServer } from './startMockCorsServer.js'
@@ -69,6 +70,7 @@ let uploadsTwo: AdminUrlUtil
 let customUploadFieldURL: AdminUrlUtil
 let hideFileInputOnCreateURL: AdminUrlUtil
 let bestFitURL: AdminUrlUtil
+let withoutEnlargementResizeOptionsURL: AdminUrlUtil
 let consoleErrorsFromPage: string[] = []
 let collectErrorsFromPage: () => boolean
 let stopCollectingErrorsFromPage: () => boolean
@@ -104,6 +106,7 @@ describe('Uploads', () => {
     customUploadFieldURL = new AdminUrlUtil(serverURL, customUploadFieldSlug)
     hideFileInputOnCreateURL = new AdminUrlUtil(serverURL, hideFileInputOnCreateSlug)
     bestFitURL = new AdminUrlUtil(serverURL, 'best-fit')
+    withoutEnlargementResizeOptionsURL = new AdminUrlUtil(serverURL, withoutEnlargeSlug)
 
     const context = await browser.newContext()
     page = await context.newPage()
@@ -1355,6 +1358,35 @@ describe('Uploads', () => {
     await expect(page.locator('.file-field .file-details__remove')).toBeHidden()
   })
 
+  test('should skip applying resizeOptions after updating an image if resizeOptions.withoutEnlargement is true and the original image size is smaller than the dimensions defined in resizeOptions', async () => {
+    await page.goto(withoutEnlargementResizeOptionsURL.create)
+
+    const fileChooserPromise = page.waitForEvent('filechooser')
+    await page.getByText('Select a file').click()
+    const fileChooser = await fileChooserPromise
+    await wait(1000)
+    await fileChooser.setFiles(path.join(dirname, 'test-image.jpg'))
+
+    await page.waitForSelector('button#action-save')
+    await page.locator('button#action-save').click()
+    await expect(page.locator('.payload-toast-container')).toContainText('successfully')
+    await wait(1000)
+
+    await page.locator('.file-field__edit').click()
+
+    // no need to make any changes to the image if resizeOptions.withoutEnlargement is actually being respected now
+    await page.locator('button:has-text("Apply Changes")').click()
+    await page.waitForSelector('button#action-save')
+    await page.locator('button#action-save').click()
+    await expect(page.locator('.payload-toast-container')).toContainText('successfully')
+    await wait(1000)
+
+    const resizeOptionMedia = page.locator('.file-meta .file-meta__size-type')
+
+    // expect the image to be the original size since the original image is smaller than the dimensions defined in resizeOptions
+    await expect(resizeOptionMedia).toContainText('800x800')
+  })
+
   describe('imageSizes best fit', () => {
     test('should select adminThumbnail if one exists', async () => {
       await page.goto(bestFitURL.create)
diff --git a/test/uploads/shared.ts b/test/uploads/shared.ts
index 02b35d43abb..9244d8018df 100644
--- a/test/uploads/shared.ts
+++ b/test/uploads/shared.ts
@@ -3,6 +3,7 @@ export const mediaSlug = 'media'
 export const relationSlug = 'relation'
 export const audioSlug = 'audio'
 export const enlargeSlug = 'enlarge'
+export const withoutEnlargeSlug = 'without-enlarge'
 export const focalNoSizesSlug = 'focal-no-sizes'
 export const focalOnlySlug = 'focal-only'
 export const reduceSlug = 'reduce'