diff --git a/CHANGELOG.md b/CHANGELOG.md
index 49ef11c3eb8..f682e74cd9a 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -48,6 +48,7 @@
 * [BUGFIX] Query-frontend: Fix shardable instant queries do not produce sorted results for `sort`, `sort_desc`, `topk`, `bottomk` functions. #5148, #5170
 * [BUGFIX] Querier: Fix `/api/v1/series` returning 5XX instead of 4XX when limits are hit. #5169
 * [BUGFIX] Compactor: Fix issue that shuffle sharding planner return error if block is under visit by other compactor. #5188
+* [BUGFIX] Fix S3 BucketWithRetries upload empty content issue #5217
 * [FEATURE] Alertmanager: Add support for time_intervals. #5102
 
 ## 1.14.0 2022-12-02
diff --git a/pkg/storage/bucket/s3/bucket_client.go b/pkg/storage/bucket/s3/bucket_client.go
index 68a8ee714f2..ad766ffb30c 100644
--- a/pkg/storage/bucket/s3/bucket_client.go
+++ b/pkg/storage/bucket/s3/bucket_client.go
@@ -6,6 +6,7 @@ import (
 	"time"
 
 	"github.com/go-kit/log"
+	"github.com/go-kit/log/level"
 	"github.com/prometheus/common/model"
 	"github.com/thanos-io/objstore"
 	"github.com/thanos-io/objstore/providers/s3"
@@ -29,6 +30,7 @@ func NewBucketClient(cfg Config, name string, logger log.Logger) (objstore.Bucke
 		return nil, err
 	}
 	return &BucketWithRetries{
+		logger:           logger,
 		bucket:           bucket,
 		operationRetries: defaultOperationRetries,
 		retryMinBackoff:  defaultRetryMinBackoff,
@@ -48,6 +50,7 @@ func NewBucketReaderClient(cfg Config, name string, logger log.Logger) (objstore
 		return nil, err
 	}
 	return &BucketWithRetries{
+		logger:           logger,
 		bucket:           bucket,
 		operationRetries: defaultOperationRetries,
 		retryMinBackoff:  defaultRetryMinBackoff,
@@ -92,6 +95,7 @@ func newS3Config(cfg Config) (s3.Config, error) {
 }
 
 type BucketWithRetries struct {
+	logger           log.Logger
 	bucket           objstore.Bucket
 	operationRetries int
 	retryMinBackoff  time.Duration
@@ -115,7 +119,10 @@ func (b *BucketWithRetries) retry(ctx context.Context, f func() error) error {
 		}
 		retries.Wait()
 	}
-	return lastErr
+	if lastErr != nil {
+		level.Error(b.logger).Log("msg", "bucket operation fail after retries", "err", lastErr)
+	}
+	return nil
 }
 
 func (b *BucketWithRetries) Name() string {
@@ -153,8 +160,17 @@ func (b *BucketWithRetries) Exists(ctx context.Context, name string) (exists boo
 }
 
 func (b *BucketWithRetries) Upload(ctx context.Context, name string, r io.Reader) error {
-	return b.retry(ctx, func() error {
+	rs, ok := r.(io.ReadSeeker)
+	if !ok {
+		// Skip retry if incoming Reader is not seekable to avoid
+		// loading entire content into memory
 		return b.bucket.Upload(ctx, name, r)
+	}
+	return b.retry(ctx, func() error {
+		if _, err := rs.Seek(0, io.SeekStart); err != nil {
+			return err
+		}
+		return b.bucket.Upload(ctx, name, rs)
 	})
 }
 
diff --git a/pkg/storage/bucket/s3/bucket_client_test.go b/pkg/storage/bucket/s3/bucket_client_test.go
new file mode 100644
index 00000000000..38e020426bb
--- /dev/null
+++ b/pkg/storage/bucket/s3/bucket_client_test.go
@@ -0,0 +1,123 @@
+package s3
+
+import (
+	"bytes"
+	"context"
+	"fmt"
+	"io"
+	"testing"
+	"time"
+
+	"github.com/stretchr/testify/require"
+	"github.com/thanos-io/objstore"
+)
+
+func TestBucketWithRetries_UploadSeekable(t *testing.T) {
+	t.Parallel()
+
+	m := mockBucket{
+		FailCount: 3,
+	}
+	b := BucketWithRetries{
+		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.NoError(t, err)
+	require.Equal(t, input, m.uploadedContent)
+}
+
+func TestBucketWithRetries_UploadNonSeekable(t *testing.T) {
+	t.Parallel()
+
+	maxFailCount := 3
+	m := mockBucket{
+		FailCount: maxFailCount,
+	}
+	b := BucketWithRetries{
+		bucket:           &m,
+		operationRetries: 5,
+		retryMinBackoff:  10 * time.Millisecond,
+		retryMaxBackoff:  time.Second,
+	}
+
+	input := &fakeReader{}
+	err := b.Upload(context.Background(), "dummy", input)
+	require.Errorf(t, err, "empty byte slice")
+	require.Equal(t, maxFailCount, m.FailCount)
+}
+
+type fakeReader struct {
+}
+
+func (f *fakeReader) Read(p []byte) (n int, err error) {
+	return 0, fmt.Errorf("empty byte slice")
+}
+
+type mockBucket struct {
+	FailCount       int
+	uploadedContent []byte
+}
+
+// Upload mocks objstore.Bucket.Upload()
+func (m *mockBucket) Upload(ctx context.Context, name string, r io.Reader) error {
+	var buf bytes.Buffer
+	if _, err := buf.ReadFrom(r); err != nil {
+		return err
+	}
+	m.uploadedContent = buf.Bytes()
+	if m.FailCount > 0 {
+		m.FailCount--
+		return fmt.Errorf("failed upload: %d", m.FailCount)
+	}
+	return nil
+}
+
+// Delete mocks objstore.Bucket.Delete()
+func (m *mockBucket) Delete(ctx context.Context, name string) error {
+	return nil
+}
+
+// Name mocks objstore.Bucket.Name()
+func (m *mockBucket) Name() string {
+	return "mock"
+}
+
+// Iter mocks objstore.Bucket.Iter()
+func (m *mockBucket) Iter(ctx context.Context, dir string, f func(string) error, options ...objstore.IterOption) error {
+	return nil
+}
+
+// Get mocks objstore.Bucket.Get()
+func (m *mockBucket) Get(ctx context.Context, name string) (io.ReadCloser, error) {
+	return nil, nil
+}
+
+// GetRange mocks objstore.Bucket.GetRange()
+func (m *mockBucket) GetRange(ctx context.Context, name string, off, length int64) (io.ReadCloser, error) {
+	return nil, nil
+}
+
+// Exists mocks objstore.Bucket.Exists()
+func (m *mockBucket) Exists(ctx context.Context, name string) (bool, error) {
+	return false, nil
+}
+
+// IsObjNotFoundErr mocks objstore.Bucket.IsObjNotFoundErr()
+func (m *mockBucket) IsObjNotFoundErr(err error) bool {
+	return false
+}
+
+// ObjectSize mocks objstore.Bucket.Attributes()
+func (m *mockBucket) Attributes(ctx context.Context, name string) (objstore.ObjectAttributes, error) {
+	return objstore.ObjectAttributes{Size: 0, LastModified: time.Now()}, nil
+}
+
+// Close mocks objstore.Bucket.Close()
+func (m *mockBucket) Close() error {
+	return nil
+}