diff --git a/pkg/storage/bucket/s3/bucket_client.go b/pkg/storage/bucket/s3/bucket_client.go
index ad766ffb30c..d0625b6deef 100644
--- a/pkg/storage/bucket/s3/bucket_client.go
+++ b/pkg/storage/bucket/s3/bucket_client.go
@@ -2,6 +2,7 @@ package s3
 
 import (
 	"context"
+	"fmt"
 	"io"
 	"time"
 
@@ -102,7 +103,7 @@ type BucketWithRetries struct {
 	retryMaxBackoff  time.Duration
 }
 
-func (b *BucketWithRetries) retry(ctx context.Context, f func() error) error {
+func (b *BucketWithRetries) retry(ctx context.Context, f func() error, operationInfo string) error {
 	var lastErr error
 	retries := backoff.New(ctx, backoff.Config{
 		MinBackoff: b.retryMinBackoff,
@@ -120,7 +121,8 @@ func (b *BucketWithRetries) retry(ctx context.Context, f func() error) error {
 		retries.Wait()
 	}
 	if lastErr != nil {
-		level.Error(b.logger).Log("msg", "bucket operation fail after retries", "err", lastErr)
+		level.Error(b.logger).Log("msg", "bucket operation fail after retries", "err", lastErr, "operation", operationInfo)
+		return lastErr
 	}
 	return nil
 }
@@ -132,14 +134,14 @@ func (b *BucketWithRetries) Name() string {
 func (b *BucketWithRetries) Iter(ctx context.Context, dir string, f func(string) error, options ...objstore.IterOption) error {
 	return b.retry(ctx, func() error {
 		return b.bucket.Iter(ctx, dir, f, options...)
-	})
+	}, fmt.Sprintf("Iter %s", dir))
 }
 
 func (b *BucketWithRetries) Get(ctx context.Context, name string) (reader io.ReadCloser, err error) {
 	err = b.retry(ctx, func() error {
 		reader, err = b.bucket.Get(ctx, name)
 		return err
-	})
+	}, fmt.Sprintf("Get %s", name))
 	return
 }
 
@@ -147,7 +149,7 @@ func (b *BucketWithRetries) GetRange(ctx context.Context, name string, off, leng
 	err = b.retry(ctx, func() error {
 		closer, err = b.bucket.GetRange(ctx, name, off, length)
 		return err
-	})
+	}, fmt.Sprintf("GetRange %s (off: %d, length: %d)", name, off, length))
 	return
 }
 
@@ -155,7 +157,7 @@ func (b *BucketWithRetries) Exists(ctx context.Context, name string) (exists boo
 	err = b.retry(ctx, func() error {
 		exists, err = b.bucket.Exists(ctx, name)
 		return err
-	})
+	}, fmt.Sprintf("Exists %s", name))
 	return
 }
 
@@ -171,21 +173,21 @@ func (b *BucketWithRetries) Upload(ctx context.Context, name string, r io.Reader
 			return err
 		}
 		return b.bucket.Upload(ctx, name, rs)
-	})
+	}, fmt.Sprintf("Upload %s", name))
 }
 
 func (b *BucketWithRetries) Attributes(ctx context.Context, name string) (attributes objstore.ObjectAttributes, err error) {
 	err = b.retry(ctx, func() error {
 		attributes, err = b.bucket.Attributes(ctx, name)
 		return err
-	})
+	}, fmt.Sprintf("Attributes %s", name))
 	return
 }
 
 func (b *BucketWithRetries) Delete(ctx context.Context, name string) error {
 	return b.retry(ctx, func() error {
 		return b.bucket.Delete(ctx, name)
-	})
+	}, fmt.Sprintf("Delete %s", name))
 }
 
 func (b *BucketWithRetries) IsObjNotFoundErr(err error) bool {
diff --git a/pkg/storage/bucket/s3/bucket_client_test.go b/pkg/storage/bucket/s3/bucket_client_test.go
index 38e020426bb..c62f9107093 100644
--- a/pkg/storage/bucket/s3/bucket_client_test.go
+++ b/pkg/storage/bucket/s3/bucket_client_test.go
@@ -8,6 +8,7 @@ import (
 	"testing"
 	"time"
 
+	"github.com/go-kit/log"
 	"github.com/stretchr/testify/require"
 	"github.com/thanos-io/objstore"
 )
@@ -19,6 +20,7 @@ func TestBucketWithRetries_UploadSeekable(t *testing.T) {
 		FailCount: 3,
 	}
 	b := BucketWithRetries{
+		logger:           log.NewNopLogger(),
 		bucket:           &m,
 		operationRetries: 5,
 		retryMinBackoff:  10 * time.Millisecond,
@@ -39,6 +41,7 @@ func TestBucketWithRetries_UploadNonSeekable(t *testing.T) {
 		FailCount: maxFailCount,
 	}
 	b := BucketWithRetries{
+		logger:           log.NewNopLogger(),
 		bucket:           &m,
 		operationRetries: 5,
 		retryMinBackoff:  10 * time.Millisecond,
@@ -51,6 +54,25 @@ func TestBucketWithRetries_UploadNonSeekable(t *testing.T) {
 	require.Equal(t, maxFailCount, m.FailCount)
 }
 
+func TestBucketWithRetries_UploadFailed(t *testing.T) {
+	t.Parallel()
+
+	m := mockBucket{
+		FailCount: 6,
+	}
+	b := BucketWithRetries{
+		logger:           log.NewNopLogger(),
+		bucket:           &m,
+		operationRetries: 5,
+		retryMinBackoff:  10 * time.Millisecond,
+		retryMaxBackoff:  time.Second,
+	}
+
+	input := []byte("test input")
+	err := b.Upload(context.Background(), "dummy", bytes.NewReader(input))
+	require.ErrorContains(t, err, "failed upload: ")
+}
+
 type fakeReader struct {
 }