diff --git a/modules/indexer/issues/indexer.go b/modules/indexer/issues/indexer.go
index 020659c82b..ef06d8862a 100644
--- a/modules/indexer/issues/indexer.go
+++ b/modules/indexer/issues/indexer.go
@@ -204,12 +204,13 @@ func getIssueIndexerQueueHandler(ctx context.Context) func(items ...*IndexerMeta
 func populateIssueIndexer(ctx context.Context) {
 	ctx, _, finished := process.GetManager().AddTypedContext(ctx, "Service: PopulateIssueIndexer", process.SystemProcessType, true)
 	defer finished()
-	if err := PopulateIssueIndexer(ctx, true); err != nil {
+	ctx = contextWithKeepRetry(ctx) // keep retrying since it's a background task
+	if err := PopulateIssueIndexer(ctx); err != nil {
 		log.Error("Issue indexer population failed: %v", err)
 	}
 }
 
-func PopulateIssueIndexer(ctx context.Context, keepRetrying bool) error {
+func PopulateIssueIndexer(ctx context.Context) error {
 	for page := 1; ; page++ {
 		select {
 		case <-ctx.Done():
@@ -232,20 +233,8 @@ func PopulateIssueIndexer(ctx context.Context, keepRetrying bool) error {
 		}
 
 		for _, repo := range repos {
-			for {
-				select {
-				case <-ctx.Done():
-					return fmt.Errorf("shutdown before completion: %w", ctx.Err())
-				default:
-				}
-				if err := updateRepoIndexer(ctx, repo.ID); err != nil {
-					if keepRetrying && ctx.Err() == nil {
-						log.Warn("Retry to populate issue indexer for repo %d: %v", repo.ID, err)
-						continue
-					}
-					return fmt.Errorf("populate issue indexer for repo %d: %v", repo.ID, err)
-				}
-				break
+			if err := updateRepoIndexer(ctx, repo.ID); err != nil {
+				return fmt.Errorf("populate issue indexer for repo %d: %v", repo.ID, err)
 			}
 		}
 	}
@@ -259,8 +248,8 @@ func UpdateRepoIndexer(ctx context.Context, repoID int64) {
 }
 
 // UpdateIssueIndexer add/update an issue to the issue indexer
-func UpdateIssueIndexer(issueID int64) {
-	if err := updateIssueIndexer(issueID); err != nil {
+func UpdateIssueIndexer(ctx context.Context, issueID int64) {
+	if err := updateIssueIndexer(ctx, issueID); err != nil {
 		log.Error("Unable to push issue %d to issue indexer: %v", issueID, err)
 	}
 }
diff --git a/modules/indexer/issues/util.go b/modules/indexer/issues/util.go
index ca4ff6d42f..510b4060b2 100644
--- a/modules/indexer/issues/util.go
+++ b/modules/indexer/issues/util.go
@@ -127,15 +127,15 @@ func updateRepoIndexer(ctx context.Context, repoID int64) error {
 		return fmt.Errorf("issue_model.GetIssueIDsByRepoID: %w", err)
 	}
 	for _, id := range ids {
-		if err := updateIssueIndexer(id); err != nil {
+		if err := updateIssueIndexer(ctx, id); err != nil {
 			return err
 		}
 	}
 	return nil
 }
 
-func updateIssueIndexer(issueID int64) error {
-	return pushIssueIndexerQueue(&IndexerMetadata{ID: issueID})
+func updateIssueIndexer(ctx context.Context, issueID int64) error {
+	return pushIssueIndexerQueue(ctx, &IndexerMetadata{ID: issueID})
 }
 
 func deleteRepoIssueIndexer(ctx context.Context, repoID int64) error {
@@ -148,13 +148,21 @@ func deleteRepoIssueIndexer(ctx context.Context, repoID int64) error {
 	if len(ids) == 0 {
 		return nil
 	}
-	return pushIssueIndexerQueue(&IndexerMetadata{
+	return pushIssueIndexerQueue(ctx, &IndexerMetadata{
 		IDs:      ids,
 		IsDelete: true,
 	})
 }
 
-func pushIssueIndexerQueue(data *IndexerMetadata) error {
+type keepRetryKey struct{}
+
+// contextWithKeepRetry returns a context with a key indicating that the indexer should keep retrying.
+// Please note that it's for background tasks only, and it should not be used for user requests, or it may cause blocking.
+func contextWithKeepRetry(ctx context.Context) context.Context {
+	return context.WithValue(ctx, keepRetryKey{}, true)
+}
+
+func pushIssueIndexerQueue(ctx context.Context, data *IndexerMetadata) error {
 	if issueIndexerQueue == nil {
 		// Some unit tests will trigger indexing, but the queue is not initialized.
 		// It's OK to ignore it, but log a warning message in case it's not a unit test.
@@ -162,12 +170,26 @@ func pushIssueIndexerQueue(data *IndexerMetadata) error {
 		return nil
 	}
 
-	err := issueIndexerQueue.Push(data)
-	if errors.Is(err, queue.ErrAlreadyInQueue) {
-		return nil
+	for {
+		select {
+		case <-ctx.Done():
+			return ctx.Err()
+		default:
+		}
+		err := issueIndexerQueue.Push(data)
+		if errors.Is(err, queue.ErrAlreadyInQueue) {
+			return nil
+		}
+		if errors.Is(err, context.DeadlineExceeded) { // the queue is full
+			log.Warn("It seems that issue indexer is slow and the queue is full. Please check the issue indexer or increase the queue size.")
+			if ctx.Value(keepRetryKey{}) == nil {
+				return err
+			}
+			// It will be better to increase the queue size instead of retrying, but users may ignore the previous warning message.
+			// However, even it retries, it may still cause index loss when there's a deadline in the context.
+			log.Debug("Retry to push %+v to issue indexer queue", data)
+			continue
+		}
+		return err
 	}
-	if errors.Is(err, context.DeadlineExceeded) {
-		log.Warn("It seems that issue indexer is slow and the queue is full. Please check the issue indexer or increase the queue size.")
-	}
-	return err
 }
diff --git a/services/cron/tasks_extended.go b/services/cron/tasks_extended.go
index b9fd1dfcff..1dd5d70a38 100644
--- a/services/cron/tasks_extended.go
+++ b/services/cron/tasks_extended.go
@@ -219,7 +219,7 @@ func registerRebuildIssueIndexer() {
 		RunAtStart: false,
 		Schedule:   "@annually",
 	}, func(ctx context.Context, _ *user_model.User, config Config) error {
-		return issue_indexer.PopulateIssueIndexer(ctx, false)
+		return issue_indexer.PopulateIssueIndexer(ctx)
 	})
 }
 
diff --git a/services/indexer/notify.go b/services/indexer/notify.go
index a07bf38b06..e0b87faedb 100644
--- a/services/indexer/notify.go
+++ b/services/indexer/notify.go
@@ -36,11 +36,11 @@ func (r *indexerNotifier) AdoptRepository(ctx context.Context, doer, u *user_mod
 func (r *indexerNotifier) CreateIssueComment(ctx context.Context, doer *user_model.User, repo *repo_model.Repository,
 	issue *issues_model.Issue, comment *issues_model.Comment, mentions []*user_model.User,
 ) {
-	issue_indexer.UpdateIssueIndexer(issue.ID)
+	issue_indexer.UpdateIssueIndexer(ctx, issue.ID)
 }
 
 func (r *indexerNotifier) NewIssue(ctx context.Context, issue *issues_model.Issue, mentions []*user_model.User) {
-	issue_indexer.UpdateIssueIndexer(issue.ID)
+	issue_indexer.UpdateIssueIndexer(ctx, issue.ID)
 }
 
 func (r *indexerNotifier) NewPullRequest(ctx context.Context, pr *issues_model.PullRequest, mentions []*user_model.User) {
@@ -48,7 +48,7 @@ func (r *indexerNotifier) NewPullRequest(ctx context.Context, pr *issues_model.P
 		log.Error("LoadIssue: %v", err)
 		return
 	}
-	issue_indexer.UpdateIssueIndexer(pr.Issue.ID)
+	issue_indexer.UpdateIssueIndexer(ctx, pr.Issue.ID)
 }
 
 func (r *indexerNotifier) UpdateComment(ctx context.Context, doer *user_model.User, c *issues_model.Comment, oldContent string) {
@@ -56,7 +56,7 @@ func (r *indexerNotifier) UpdateComment(ctx context.Context, doer *user_model.Us
 		log.Error("LoadIssue: %v", err)
 		return
 	}
-	issue_indexer.UpdateIssueIndexer(c.Issue.ID)
+	issue_indexer.UpdateIssueIndexer(ctx, c.Issue.ID)
 }
 
 func (r *indexerNotifier) DeleteComment(ctx context.Context, doer *user_model.User, comment *issues_model.Comment) {
@@ -64,7 +64,7 @@ func (r *indexerNotifier) DeleteComment(ctx context.Context, doer *user_model.Us
 		log.Error("LoadIssue: %v", err)
 		return
 	}
-	issue_indexer.UpdateIssueIndexer(comment.Issue.ID)
+	issue_indexer.UpdateIssueIndexer(ctx, comment.Issue.ID)
 }
 
 func (r *indexerNotifier) DeleteRepository(ctx context.Context, doer *user_model.User, repo *repo_model.Repository) {
@@ -120,13 +120,13 @@ func (r *indexerNotifier) ChangeDefaultBranch(ctx context.Context, repo *repo_mo
 }
 
 func (r *indexerNotifier) IssueChangeContent(ctx context.Context, doer *user_model.User, issue *issues_model.Issue, oldContent string) {
-	issue_indexer.UpdateIssueIndexer(issue.ID)
+	issue_indexer.UpdateIssueIndexer(ctx, issue.ID)
 }
 
 func (r *indexerNotifier) IssueChangeTitle(ctx context.Context, doer *user_model.User, issue *issues_model.Issue, oldTitle string) {
-	issue_indexer.UpdateIssueIndexer(issue.ID)
+	issue_indexer.UpdateIssueIndexer(ctx, issue.ID)
 }
 
 func (r *indexerNotifier) IssueChangeRef(ctx context.Context, doer *user_model.User, issue *issues_model.Issue, oldRef string) {
-	issue_indexer.UpdateIssueIndexer(issue.ID)
+	issue_indexer.UpdateIssueIndexer(ctx, issue.ID)
 }
diff --git a/tests/integration/issue_test.go b/tests/integration/issue_test.go
index 853e565b0f..ac06b487db 100644
--- a/tests/integration/issue_test.go
+++ b/tests/integration/issue_test.go
@@ -4,6 +4,7 @@
 package integration
 
 import (
+	"context"
 	"fmt"
 	"net/http"
 	"net/url"
@@ -99,7 +100,7 @@ func TestViewIssuesKeyword(t *testing.T) {
 		RepoID: repo.ID,
 		Index:  1,
 	})
-	issues.UpdateIssueIndexer(issue.ID)
+	issues.UpdateIssueIndexer(context.Background(), issue.ID)
 	time.Sleep(time.Second * 1)
 	const keyword = "first"
 	req := NewRequestf(t, "GET", "%s/issues?q=%s", repo.Link(), keyword)