diff --git a/.changeset/rude-onions-smoke.md b/.changeset/rude-onions-smoke.md
new file mode 100644
index 000000000..655a728c3
--- /dev/null
+++ b/.changeset/rude-onions-smoke.md
@@ -0,0 +1,5 @@
+---
+"@uppy/core": patch
+---
+
+Fix retry after setting missed metaFields requiring you to click "retry" and then "upload" again. Now "retry" immediately restarts the upload.
diff --git a/packages/@uppy/core/src/Uppy.test.ts b/packages/@uppy/core/src/Uppy.test.ts
index 6223706c0..acfd68079 100644
--- a/packages/@uppy/core/src/Uppy.test.ts
+++ b/packages/@uppy/core/src/Uppy.test.ts
@@ -1472,6 +1472,163 @@ describe('src/Core', () => {
       await core.retryAll()
       expect(onUpload).not.toHaveBeenCalled()
     })
+
+    describe('with required metadata', () => {
+      it('should not retry files that have missing required metadata', async () => {
+        const onUpload = vi.fn()
+        const onRetryAll = vi.fn()
+
+        const core = new Core({
+          restrictions: {
+            requiredMetaFields: ['caption'],
+          },
+        })
+        core.on('upload', onUpload)
+        core.on('retry-all', onRetryAll)
+
+        const fileId = core.addFile({
+          source: 'vi',
+          name: 'foo.jpg',
+          type: 'image/jpeg',
+          data: testImage,
+        })
+
+        // Simulate an upload attempt which triggers metadata validation
+        try {
+          await core.upload()
+        } catch (error) {
+          expect(error).toBeInstanceOf(RestrictionError)
+          expect(error.message).toContain('Missing required meta fields')
+        }
+
+        // File should now have missing metadata error after upload attempt
+        const file = core.getFile(fileId)
+        expect(file.missingRequiredMetaFields).toEqual(['caption'])
+        expect(file.error).toContain('Missing required meta fields in foo.jpg')
+
+        // Should not retry files with outstanding metadata issues
+        await core.retryAll()
+        expect(onRetryAll.mock.calls[0][0]).toEqual([])
+        expect(onUpload).toHaveBeenCalledTimes(0)
+      })
+
+      it('should retry files after metadata is corrected', async () => {
+        const onUpload = vi.fn()
+        const onRetryAll = vi.fn()
+
+        const core = new Core({
+          restrictions: {
+            requiredMetaFields: ['caption'],
+          },
+        })
+        core.on('upload', onUpload)
+        core.on('retry-all', onRetryAll)
+
+        const fileId = core.addFile({
+          source: 'vi',
+          name: 'foo.jpg',
+          type: 'image/jpeg',
+          data: testImage,
+        })
+
+        try {
+          await core.upload()
+        } catch (error) {
+          expect(error).toBeInstanceOf(RestrictionError)
+          expect(error.message).toContain('Missing required meta fields')
+        }
+
+        // Verify file has missing metadata error after upload attempt
+        const file = core.getFile(fileId)
+        expect(file.missingRequiredMetaFields).toEqual(['caption'])
+        expect(file.error).toContain('Missing required meta fields in foo.jpg')
+
+        // Fix the metadata
+        core.setFileMeta(fileId, { caption: 'Test caption' })
+
+        // Trigger the dashboard:file-edit-complete event to update validation state
+        // @ts-ignore
+        core.emit('dashboard:file-edit-complete', core.getFile(fileId))
+
+        const updatedFile = core.getFile(fileId)
+        expect(updatedFile.missingRequiredMetaFields).toEqual([])
+
+        // Now retry should work
+        await core.retryAll()
+        expect(onRetryAll.mock.calls[0][0]).toContainEqual(
+          expect.objectContaining({ id: fileId }),
+        )
+        expect(onUpload).toHaveBeenCalledTimes(1) // Called once during retry (initial upload failed at validation)
+      })
+
+      it('should handle multiple files with mixed metadata states', async () => {
+        const onUpload = vi.fn()
+        const onRetryAll = vi.fn()
+
+        const core = new Core({
+          restrictions: {
+            requiredMetaFields: ['caption'],
+          },
+        })
+        core.on('upload', onUpload)
+        core.on('retry-all', onRetryAll)
+
+        // Add files with missing metadata
+        const fileId1 = core.addFile({
+          source: 'vi',
+          name: 'file1.jpg',
+          type: 'image/jpeg',
+          data: testImage,
+        })
+        const _fileId2 = core.addFile({
+          source: 'vi',
+          name: 'file2.jpg',
+          type: 'image/jpeg',
+          data: testImage,
+        })
+        const fileId3 = core.addFile({
+          source: 'vi',
+          name: 'file3.jpg',
+          type: 'image/jpeg',
+          data: testImage,
+        })
+
+        try {
+          await core.upload()
+        } catch (error) {
+          expect(error).toBeInstanceOf(RestrictionError)
+          expect(error.message).toContain('Missing required meta fields')
+        }
+
+        // Give one file a different error (not metadata-related)
+        core.setFileState(fileId3, {
+          error: 'Network error',
+          missingRequiredMetaFields: [],
+        })
+
+        // Fix metadata for first file only
+        core.setFileMeta(fileId1, { caption: 'Fixed caption' })
+        // @ts-ignore
+        core.emit('dashboard:file-edit-complete', core.getFile(fileId1))
+
+        // Add an error to file1 so it can be retried
+        core.setFileState(fileId1, {
+          error: 'Upload failed',
+        })
+
+        // Retry should only include file1 and file3 (file2 still has missing metadata)
+        await core.retryAll()
+
+        const retriedFiles = onRetryAll.mock.calls[0][0]
+        expect(retriedFiles).toContainEqual(
+          expect.objectContaining({ id: fileId1 }),
+        )
+        expect(retriedFiles).toContainEqual(
+          expect.objectContaining({ id: fileId3 }),
+        )
+        expect(onUpload).toHaveBeenCalledTimes(1)
+      })
+    })
   })
 
   describe('restoring a file', () => {
diff --git a/packages/@uppy/core/src/Uppy.ts b/packages/@uppy/core/src/Uppy.ts
index f9fdec98e..85c3e4946 100644
--- a/packages/@uppy/core/src/Uppy.ts
+++ b/packages/@uppy/core/src/Uppy.ts
@@ -918,13 +918,18 @@ export class Uppy<
       this.#restricter.getMissingRequiredMetaFields(file)
 
     if (missingFields.length > 0) {
-      this.setFileState(file.id, { missingRequiredMetaFields: missingFields })
+      this.setFileState(file.id, {
+        missingRequiredMetaFields: missingFields,
+        error: error.message,
+      })
       this.log(error.message)
       this.emit('restriction-failed', file, error)
       return false
     }
     if (missingFields.length === 0 && file.missingRequiredMetaFields) {
-      this.setFileState(file.id, { missingRequiredMetaFields: [] })
+      this.setFileState(file.id, {
+        missingRequiredMetaFields: [],
+      })
     }
     return true
   }
@@ -1378,8 +1383,14 @@ export class Uppy<
 
   #getFilesToRetry() {
     const { files } = this.getState()
-    return Object.keys(files).filter((file) => {
-      return files[file].error
+    return Object.keys(files).filter((fileId) => {
+      const file = files[fileId]
+      // Only retry files that have errors AND don't have missing required metadata
+      return (
+        file.error &&
+        (!file.missingRequiredMetaFields ||
+          file.missingRequiredMetaFields.length === 0)
+      )
     })
   }