diff --git a/internal/store/store.go b/internal/store/store.go
index 63a87b8..8a5b07f 100644
--- a/internal/store/store.go
+++ b/internal/store/store.go
@@ -496,9 +496,41 @@ INSERT INTO pending_approvals (
 	message_chat_id, message_id, status
 ) VALUES (?, ?, ?, ?, ?, ?, ?, ?, ?, 'pending')
 ON CONFLICT(telegram_user_id, codex_request_id) DO UPDATE SET
+	codex_thread_id = excluded.codex_thread_id,
+	turn_id = excluded.turn_id,
+	item_id = excluded.item_id,
+	kind = excluded.kind,
 	payload_json = excluded.payload_json,
-	message_chat_id = CASE WHEN pending_approvals.status = 'pending' THEN excluded.message_chat_id ELSE pending_approvals.message_chat_id END,
-	message_id = CASE WHEN pending_approvals.status = 'pending' THEN excluded.message_id ELSE pending_approvals.message_id END`,
+	message_chat_id = CASE
+		WHEN pending_approvals.codex_thread_id = excluded.codex_thread_id
+			AND pending_approvals.turn_id = excluded.turn_id
+			AND pending_approvals.item_id = excluded.item_id
+		THEN pending_approvals.message_chat_id
+		ELSE excluded.message_chat_id
+	END,
+	message_id = CASE
+		WHEN pending_approvals.codex_thread_id = excluded.codex_thread_id
+			AND pending_approvals.turn_id = excluded.turn_id
+			AND pending_approvals.item_id = excluded.item_id
+		THEN pending_approvals.message_id
+		ELSE excluded.message_id
+	END,
+	status = CASE
+		WHEN pending_approvals.status <> 'pending'
+			AND pending_approvals.codex_thread_id = excluded.codex_thread_id
+			AND pending_approvals.turn_id = excluded.turn_id
+			AND pending_approvals.item_id = excluded.item_id
+		THEN pending_approvals.status
+		ELSE 'pending'
+	END,
+	resolved_at = CASE
+		WHEN pending_approvals.status <> 'pending'
+			AND pending_approvals.codex_thread_id = excluded.codex_thread_id
+			AND pending_approvals.turn_id = excluded.turn_id
+			AND pending_approvals.item_id = excluded.item_id
+		THEN pending_approvals.resolved_at
+		ELSE ''
+	END`,
 		approval.TelegramUserID, approval.CodexRequestID, approval.CodexThreadID, approval.TurnID,
 		approval.ItemID, approval.Kind, approval.PayloadJSON, approval.MessageChatID, approval.MessageID)
 	if err != nil {
diff --git a/internal/store/store_test.go b/internal/store/store_test.go
index 464c669..bb5553a 100644
--- a/internal/store/store_test.go
+++ b/internal/store/store_test.go
@@ -267,6 +267,62 @@ func TestUpsertPendingApprovalDoesNotReopenResolved(t *testing.T) {
 	}
 }
 
+func TestUpsertPendingApprovalReopensReusedRequestIDForNewContext(t *testing.T) {
+	ctx := context.Background()
+	st, err := Open(ctx, filepath.Join(t.TempDir(), "bot.db"))
+	if err != nil {
+		t.Fatal(err)
+	}
+	defer st.Close()
+
+	first, err := st.UpsertPendingApproval(ctx, PendingApproval{
+		TelegramUserID: 42,
+		CodexRequestID: "i:0",
+		CodexThreadID:  "thread-1",
+		TurnID:         "turn-1",
+		ItemID:         "item-1",
+		Kind:           "item/commandExecution/requestApproval",
+		PayloadJSON:    `{"command":"go test ./..."}`,
+	})
+	if err != nil {
+		t.Fatal(err)
+	}
+	if err := st.UpdatePendingApprovalMessage(ctx, first.ID, 1001, 2002); err != nil {
+		t.Fatal(err)
+	}
+	if err := st.ResolvePendingApproval(ctx, 42, first.ID, "accept"); err != nil {
+		t.Fatal(err)
+	}
+
+	second, err := st.UpsertPendingApproval(ctx, PendingApproval{
+		TelegramUserID: 42,
+		CodexRequestID: "i:0",
+		CodexThreadID:  "thread-2",
+		TurnID:         "turn-2",
+		ItemID:         "item-2",
+		Kind:           "item/commandExecution/requestApproval",
+		PayloadJSON:    `{"command":"git push"}`,
+	})
+	if err != nil {
+		t.Fatal(err)
+	}
+	if second.ID != first.ID {
+		t.Fatalf("reused request id row = %d, want %d", second.ID, first.ID)
+	}
+	if second.Status != "pending" {
+		t.Fatalf("reused request status = %q, want pending", second.Status)
+	}
+	if second.CodexThreadID != "thread-2" || second.TurnID != "turn-2" || second.ItemID != "item-2" {
+		t.Fatalf("reused request context = thread %q turn %q item %q", second.CodexThreadID, second.TurnID, second.ItemID)
+	}
+	if second.MessageChatID != 0 || second.MessageID != 0 {
+		t.Fatalf("reused request kept stale message: chat=%d message=%d", second.MessageChatID, second.MessageID)
+	}
+	if second.ResolvedAt != "" {
+		t.Fatalf("reused request resolved_at = %q, want empty", second.ResolvedAt)
+	}
+}
+
 func TestValidateWorkspacePath(t *testing.T) {
 	if _, err := ValidateWorkspacePath("relative/path"); err == nil {
 		t.Fatal("relative path should be rejected")
diff --git a/internal/telegram/bot.go b/internal/telegram/bot.go
index 4314f9b..40c023c 100644
--- a/internal/telegram/bot.go
+++ b/internal/telegram/bot.go
@@ -1878,6 +1878,7 @@ func (b *Bot) handleCodexServerRequest(ctx context.Context, event codexapp.Event
 	if err != nil {
 		return err
 	}
+	b.logger.Printf("codex approval thread mapped: request=%s telegram_user=%d", event.ID.Key(), thread.TelegramUserID)
 	pretty, _ := json.MarshalIndent(json.RawMessage(event.Params), "", "  ")
 	if len(pretty) == 0 {
 		pretty = event.Params
@@ -1895,15 +1896,18 @@ func (b *Bot) handleCodexServerRequest(ctx context.Context, event codexapp.Event
 	if err != nil {
 		return err
 	}
+	b.logger.Printf("codex approval stored: request=%s approval_id=%d status=%s item=%s", event.ID.Key(), approval.ID, approval.Status, approval.ItemID)
 	if approval.Status != "pending" {
 		return nil
 	}
 	text := renderApprovalHTML(kind, event.Params, "")
 	markup := approvalMarkupForPayload(approval.ID, event.Params)
+	b.logger.Printf("codex approval render complete: request=%s approval_id=%d text_runes=%d", event.ID.Key(), approval.ID, len([]rune(text)))
 	msg, err := b.upsertApprovalMessage(ctx, thread.TelegramUserID, threadID, params.TurnID, itemID, text, markup)
 	if err != nil {
 		return err
 	}
+	b.logger.Printf("codex approval telegram sent: request=%s approval_id=%d chat=%d message=%d", event.ID.Key(), approval.ID, msg.Chat.ID, msg.MessageID)
 	return b.store.UpdatePendingApprovalMessage(ctx, approval.ID, msg.Chat.ID, msg.MessageID)
 }
 
@@ -2316,15 +2320,34 @@ func (b *Bot) upsertApprovalMessage(ctx context.Context, chatID int64, threadID,
 	if approvalHTML == "" {
 		return Message{}, errors.New("approval message is empty")
 	}
-	if threadID == "" || itemID == "" || !b.hasOutputTurn(threadID, turnID) {
-		return b.tg.SendMessage(ctx, chatID, approvalHTML, SendMessageOptions{ParseMode: "HTML", ReplyMarkup: markup})
+	b.logger.Printf("codex approval ui upsert start: thread=%s turn=%s item=%s chat=%d text_runes=%d", threadID, turnID, itemID, chatID, len([]rune(approvalHTML)))
+	trackedTurn := threadID != "" && itemID != "" && b.hasOutputTurn(threadID, turnID)
+	if !trackedTurn {
+		b.logger.Printf("codex approval ui direct send start: thread=%s turn=%s item=%s chat=%d", threadID, turnID, itemID, chatID)
+		msg, err := b.tg.SendMessage(ctx, chatID, approvalHTML, SendMessageOptions{ParseMode: "HTML", ReplyMarkup: markup})
+		if err != nil {
+			b.logger.Printf("codex approval ui direct send failed: thread=%s turn=%s item=%s err=%v", threadID, turnID, itemID, err)
+			return Message{}, err
+		}
+		b.logger.Printf("codex approval ui direct send done: thread=%s turn=%s item=%s chat=%d message=%d", threadID, turnID, itemID, msg.Chat.ID, msg.MessageID)
+		return msg, nil
 	}
+	b.logger.Printf("codex approval ui flush assistant start: thread=%s turn=%s item=%s", threadID, turnID, itemID)
 	if err := b.flushAssistantMessage(ctx, threadID); err != nil {
+		b.logger.Printf("codex approval ui flush assistant failed: thread=%s turn=%s item=%s err=%v", threadID, turnID, itemID, err)
 		return Message{}, err
 	}
+	b.logger.Printf("codex approval ui flush assistant done: thread=%s turn=%s item=%s", threadID, turnID, itemID)
 	trackedChatID, err := b.outputChatID(ctx, threadID)
 	if err != nil {
-		return b.tg.SendMessage(ctx, chatID, approvalHTML, SendMessageOptions{ParseMode: "HTML", ReplyMarkup: markup})
+		b.logger.Printf("codex approval ui output state missing; direct send start: thread=%s turn=%s item=%s chat=%d err=%v", threadID, turnID, itemID, chatID, err)
+		msg, sendErr := b.tg.SendMessage(ctx, chatID, approvalHTML, SendMessageOptions{ParseMode: "HTML", ReplyMarkup: markup})
+		if sendErr != nil {
+			b.logger.Printf("codex approval ui output-state direct send failed: thread=%s turn=%s item=%s err=%v", threadID, turnID, itemID, sendErr)
+			return Message{}, sendErr
+		}
+		b.logger.Printf("codex approval ui output-state direct send done: thread=%s turn=%s item=%s chat=%d message=%d", threadID, turnID, itemID, msg.Chat.ID, msg.MessageID)
+		return msg, nil
 	}
 	chatID = trackedChatID
 
@@ -2343,20 +2366,24 @@ func (b *Bot) upsertApprovalMessage(ctx context.Context, chatID int64, threadID,
 			combined := tool.html()
 			msg := Message{MessageID: tool.messageID, Chat: Chat{ID: tool.chatID}}
 			b.mu.Unlock()
+			b.logger.Printf("codex approval ui edit start: thread=%s turn=%s item=%s chat=%d message=%d text_runes=%d", threadID, turnID, itemID, msg.Chat.ID, msg.MessageID, len([]rune(combined)))
 			_, err := b.tg.EditMessageText(ctx, msg.Chat.ID, msg.MessageID, combined, EditMessageTextOptions{ParseMode: "HTML", ReplyMarkup: editReplyMarkup(markup)})
 			if err := ignoreTelegramMessageNotModified(err); err != nil {
 				b.clearToolApproval(threadID, itemID)
-				b.logger.Printf("edit tool approval message %s/%s: %v", threadID, itemID, err)
+				b.logger.Printf("codex approval ui edit failed: thread=%s turn=%s item=%s err=%v", threadID, turnID, itemID, err)
 				return Message{}, err
 			}
+			b.logger.Printf("codex approval ui edit done: thread=%s turn=%s item=%s chat=%d message=%d", threadID, turnID, itemID, msg.Chat.ID, msg.MessageID)
 			b.markOutputSent(threadID)
 			return msg, nil
 		}
 	}
 	b.mu.Unlock()
 
+	b.logger.Printf("codex approval ui new combined message start: thread=%s turn=%s item=%s chat=%d", threadID, turnID, itemID, chatID)
 	msg, err := b.sendHTMLMessage(ctx, chatID, approvalHTML, markup)
 	if err != nil {
+		b.logger.Printf("codex approval ui new combined message failed: thread=%s turn=%s item=%s err=%v", threadID, turnID, itemID, err)
 		return Message{}, err
 	}
 	b.mu.Lock()
@@ -2368,6 +2395,7 @@ func (b *Bot) upsertApprovalMessage(ctx context.Context, chatID int64, threadID,
 		state.tools[itemID] = toolMessageState{chatID: msg.Chat.ID, messageID: msg.MessageID, approvalHTML: approvalHTML, approvalMarkup: markup}
 	}
 	b.mu.Unlock()
+	b.logger.Printf("codex approval ui new combined message done: thread=%s turn=%s item=%s chat=%d message=%d", threadID, turnID, itemID, msg.Chat.ID, msg.MessageID)
 	b.markOutputSent(threadID)
 	return msg, nil
 }