diff --git a/flytecopilot/data/retry.go b/flytecopilot/data/retry.go
new file mode 100644
index 00000000000..a8e1e9109f3
--- /dev/null
+++ b/flytecopilot/data/retry.go
@@ -0,0 +1,41 @@
+package data
+
+import (
+	"context"
+	"time"
+
+	"github.com/flyteorg/flyte/flytestdlib/logger"
+)
+
+const (
+	uploadFileRetryMaxAttemptIndex = 5
+	uploadFileRetryDelay           = 2 * time.Second
+)
+
+// See flyteadmin/pkg/async.RetryOnSpecificErrors
+func retryOnSpecificErrors(ctx context.Context, attempts int, delay time.Duration, f func() error, isErrorRetryable func(error) bool) error {
+	var err error
+	for attempt := 0; attempt <= attempts; attempt++ {
+		err = f()
+		if err == nil {
+			return nil
+		}
+		if !isErrorRetryable(err) {
+			return err
+		}
+		if attempt == attempts {
+			return err
+		}
+		logger.Warningf(ctx, "Failed [%v] on attempt %d of %d; retrying after %v", err, attempt, attempts, delay)
+		select {
+		case <-time.After(delay):
+		case <-ctx.Done():
+			return ctx.Err()
+		}
+	}
+	return err
+}
+
+func retryOnAllErrors(err error) bool {
+	return true
+}
diff --git a/flytecopilot/data/retry_test.go b/flytecopilot/data/retry_test.go
new file mode 100644
index 00000000000..9be78ad0364
--- /dev/null
+++ b/flytecopilot/data/retry_test.go
@@ -0,0 +1,41 @@
+package data
+
+import (
+	"context"
+	"testing"
+	"time"
+
+	"github.com/pkg/errors"
+	"github.com/stretchr/testify/assert"
+)
+
+var s3LikeError = errors.Wrap(errors.New(
+	`Put "https://example.s3.us-west-2.amazonaws.com/key?partNumber=11&uploadId=x": http: server closed idle connection`),
+	`PutObject, putting object: MultipartUpload: upload multipart failed
+caused by: RequestError: send request failed
+caused by: Put "https://example.s3.us-west-2.amazonaws.com/key?partNumber=11&uploadId=x"`)
+
+func TestRetryOnSpecificErrors_SucceedsFirstTry(t *testing.T) {
+	ctx := context.Background()
+	calls := 0
+	err := retryOnSpecificErrors(ctx, 3, time.Millisecond, func() error {
+		calls++
+		return nil
+	}, retryOnAllErrors)
+	assert.NoError(t, err)
+	assert.Equal(t, 1, calls)
+}
+
+func TestRetryOnSpecificErrors_RetriesThenSucceeds(t *testing.T) {
+	ctx := context.Background()
+	calls := 0
+	err := retryOnSpecificErrors(ctx, 5, time.Millisecond, func() error {
+		calls++
+		if calls < 3 {
+			return s3LikeError
+		}
+		return nil
+	}, retryOnAllErrors)
+	assert.NoError(t, err)
+	assert.Equal(t, 3, calls)
+}
diff --git a/flytecopilot/data/utils.go b/flytecopilot/data/utils.go
index 923c75f908b..0b229118a2e 100644
--- a/flytecopilot/data/utils.go
+++ b/flytecopilot/data/utils.go
@@ -46,17 +46,18 @@ func IsFileReadable(fpath string, ignoreExtension bool) (string, os.FileInfo, er
 
 // Uploads a file to the data store.
 func UploadFileToStorage(ctx context.Context, filePath string, toPath storage.DataReference, size int64, store *storage.DataStore) error {
-	f, err := os.Open(filePath)
-	if err != nil {
-		return err
-	}
-	defer func() {
-		err := f.Close()
+	return retryOnSpecificErrors(ctx, uploadFileRetryMaxAttemptIndex, uploadFileRetryDelay, func() error {
+		f, err := os.Open(filePath)
 		if err != nil {
-			logger.Errorf(ctx, "failed to close blob file at path [%s]", filePath)
+			return err
 		}
-	}()
-	return store.WriteRaw(ctx, toPath, size, storage.Options{}, f)
+		defer func() {
+			if cerr := f.Close(); cerr != nil {
+				logger.Errorf(ctx, "failed to close blob file at path [%s]", filePath)
+			}
+		}()
+		return store.WriteRaw(ctx, toPath, size, storage.Options{}, f)
+	}, retryOnAllErrors)
 }
 
 func DownloadFileFromStorage(ctx context.Context, ref storage.DataReference, store *storage.DataStore) (io.ReadCloser, error) {