diff --git a/internal/write/service.go b/internal/write/service.go
index 2d6985fa..9e54bd33 100644
--- a/internal/write/service.go
+++ b/internal/write/service.go
@@ -124,6 +124,17 @@ func (w *Service) HandleWrite(ctx context.Context, batch *Batch) error {
 			log.Debug("Write proc: taking batch from retry queue")
 			if !retrying {
 				b := w.retryQueue.first()
+
+				// Discard batches at beginning of retryQueue that have already expired
+				if time.Now().After(b.Expires) {
+					log.Warn("Write proc: oldest batch in retry queue expired, discarding")
+					if !b.Evicted {
+						w.retryQueue.pop()
+					}
+
+					continue
+				}
+
 				// Can we write? In case of retryable error we must wait a bit
 				if w.lastWriteAttempt.IsZero() || time.Now().After(w.lastWriteAttempt.Add(time.Millisecond*time.Duration(b.RetryDelay))) {
 					retrying = true
@@ -147,12 +158,6 @@ func (w *Service) HandleWrite(ctx context.Context, batch *Batch) error {
 		}
 		// write batch
 		if batchToWrite != nil {
-			if time.Now().After(batchToWrite.Expires) {
-				if !batchToWrite.Evicted {
-					w.retryQueue.pop()
-				}
-				return fmt.Errorf("write failed (attempts %d): max retry time exceeded", batchToWrite.RetryAttempts)
-			}
 			perror := w.WriteBatch(ctx, batchToWrite)
 			if perror != nil {
 				if w.writeOptions.MaxRetries() != 0 && (perror.StatusCode == 0 || perror.StatusCode >= http.StatusTooManyRequests) {
diff --git a/internal/write/service_test.go b/internal/write/service_test.go
index a0525712..ed4c1f73 100644
--- a/internal/write/service_test.go
+++ b/internal/write/service_test.go
@@ -9,6 +9,7 @@ import (
 	"errors"
 	"fmt"
 	ilog "log"
+	"runtime"
 	"strings"
 	"sync"
 	"testing"
@@ -313,14 +314,23 @@ func TestMaxRetryTime(t *testing.T) {
 
 	// Wait for batch expiration
 	<-time.After(5 * time.Millisecond)
-	b := NewBatch("2\n", opts.RetryInterval(), opts.MaxRetryTime())
-	// First batch will be tried to write again and it will be checked agains maxRetryTime. New batch will added to retry queue
+
+	exp := opts.MaxRetryTime()
+	// sleep takes at least more than 10ms (sometimes 15ms) on Windows https://github.com/golang/go/issues/44343
+	if runtime.GOOS == "windows" {
+		exp = 20
+	}
+	// create new batch for sending
+	b := NewBatch("2\n", opts.RetryInterval(), exp)
+	// First batch will  be checked against maxRetryTime and it will expire. New batch will fail and it will added to retry queue
 	err = srv.HandleWrite(ctx, b)
 	require.NotNil(t, err)
-	// Error about batch expiration
-	assert.Equal(t, "write failed (attempts 1): max retry time exceeded", err.Error())
+	// 1st Batch expires and writing 2nd trows error
+	assert.Equal(t, "write failed (attempts 1): Unexpected status code 429", err.Error())
 	assert.Equal(t, 1, srv.retryQueue.list.Len())
 
+	//wait minimum retry time
+	<-time.After(time.Millisecond)
 	// Clear error and let write pass
 	hs.SetReplyError(nil)
 	// A batch from retry queue will be sent first