diff --git a/internal/store/store.go b/internal/store/store.go
index d7cc7e1..7edc692 100644
--- a/internal/store/store.go
+++ b/internal/store/store.go
@@ -460,10 +460,8 @@ INSERT INTO pending_approvals (
 ) VALUES (?, ?, ?, ?, ?, ?, ?, ?, ?, 'pending')
 ON CONFLICT(telegram_user_id, codex_request_id) DO UPDATE SET
 	payload_json = excluded.payload_json,
-	message_chat_id = excluded.message_chat_id,
-	message_id = excluded.message_id,
-	status = 'pending',
-	resolved_at = ''`,
+	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`,
 		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 f3dc28a..bf477e4 100644
--- a/internal/store/store_test.go
+++ b/internal/store/store_test.go
@@ -192,6 +192,57 @@ func TestRenameThread(t *testing.T) {
 	}
 }
 
+func TestUpsertPendingApprovalDoesNotReopenResolved(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: "request-1",
+		CodexThreadID:  "thread-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: "request-1",
+		CodexThreadID:  "thread-1",
+		Kind:           "item/commandExecution/requestApproval",
+		PayloadJSON:    `{"command":"go test ./...","duplicate":true}`,
+		MessageChatID:  3003,
+		MessageID:      4004,
+	})
+	if err != nil {
+		t.Fatal(err)
+	}
+	if second.ID != first.ID {
+		t.Fatalf("duplicate approval id = %d, want %d", second.ID, first.ID)
+	}
+	if second.Status != "accept" {
+		t.Fatalf("duplicate approval status = %q, want accept", second.Status)
+	}
+	if second.MessageChatID != 1001 || second.MessageID != 2002 {
+		t.Fatalf("resolved approval message changed: chat=%d message=%d", second.MessageChatID, second.MessageID)
+	}
+	if second.ResolvedAt == "" {
+		t.Fatal("resolved approval lost resolved_at")
+	}
+}
+
 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 0dbbea7..85147f8 100644
--- a/internal/telegram/bot.go
+++ b/internal/telegram/bot.go
@@ -329,7 +329,7 @@ func (b *Bot) sendResumeChoices(ctx context.Context, userID, chatID int64, page
 	text := resumeThreadListText(threads, page)
 	markup := resumeThreadMarkup(threads, page, hasNext)
 	if messageID != 0 {
-		_, err := b.tg.EditMessageText(ctx, chatID, messageID, EscapeHTML(text), EditMessageTextOptions{ParseMode: "HTML", ReplyMarkup: markup})
+		_, err := b.tg.EditMessageText(ctx, chatID, messageID, EscapeHTML(text), EditMessageTextOptions{ParseMode: "HTML", ReplyMarkup: editReplyMarkup(markup)})
 		return err
 	}
 	_, err = b.tg.SendMessage(ctx, chatID, EscapeHTML(text), SendMessageOptions{ParseMode: "HTML", ReplyMarkup: markup})
@@ -366,7 +366,7 @@ func (b *Bot) resumeThreadByID(ctx context.Context, userID, chatID int64, id int
 	}
 	text := fmt.Sprintf("Active thread ID %d: %s", thread.ID, threadDisplayTitle(thread))
 	if messageID != 0 {
-		_, err = b.tg.EditMessageText(ctx, chatID, messageID, EscapeHTML(text), EditMessageTextOptions{ParseMode: "HTML"})
+		_, err = b.tg.EditMessageText(ctx, chatID, messageID, EscapeHTML(text), EditMessageTextOptions{ParseMode: "HTML", ReplyMarkup: clearInlineKeyboardMarkup()})
 		return err
 	}
 	_, err = b.tg.SendMessage(ctx, chatID, EscapeHTML(text), SendMessageOptions{ParseMode: "HTML"})
@@ -1149,7 +1149,7 @@ func (b *Bot) handleApprovalCallback(ctx context.Context, callback *CallbackQuer
 		return err
 	}
 	updated := b.resolveApprovalMessageHTML(approval, decision)
-	_, err = b.tg.EditMessageText(ctx, callback.Message.Chat.ID, callback.Message.MessageID, updated, EditMessageTextOptions{ParseMode: "HTML"})
+	_, err = b.tg.EditMessageText(ctx, callback.Message.Chat.ID, callback.Message.MessageID, updated, EditMessageTextOptions{ParseMode: "HTML", ReplyMarkup: clearInlineKeyboardMarkup()})
 	return ignoreTelegramMessageNotModified(err)
 }
 
@@ -1710,6 +1710,9 @@ func (b *Bot) handleCodexServerRequest(ctx context.Context, event codexapp.Event
 	if err != nil {
 		return err
 	}
+	if approval.Status != "pending" {
+		return nil
+	}
 	text := renderApprovalHTML(kind, event.Params, "")
 	markup := approvalMarkup(approval.ID)
 	if msg, ok, err := b.attachApprovalToToolMessage(ctx, params.ThreadID, params.ItemID, text, markup); err != nil {
@@ -2023,7 +2026,7 @@ func (b *Bot) upsertToolMessage(ctx context.Context, threadID, itemID, htmlText
 			msgID := tool.messageID
 			markup := tool.approvalMarkup
 			b.mu.Unlock()
-			_, err := b.tg.EditMessageText(ctx, msgChatID, msgID, combined, EditMessageTextOptions{ParseMode: "HTML", ReplyMarkup: markup})
+			_, err := b.tg.EditMessageText(ctx, msgChatID, msgID, combined, EditMessageTextOptions{ParseMode: "HTML", ReplyMarkup: editReplyMarkup(markup)})
 			if err := ignoreTelegramMessageNotModified(err); err != nil {
 				return err
 			}
@@ -2078,7 +2081,7 @@ func (b *Bot) attachApprovalToToolMessage(ctx context.Context, threadID, itemID,
 	msg := Message{MessageID: tool.messageID, Chat: Chat{ID: tool.chatID}}
 	b.mu.Unlock()
 
-	_, err := b.tg.EditMessageText(ctx, msg.Chat.ID, msg.MessageID, combined, EditMessageTextOptions{ParseMode: "HTML", ReplyMarkup: markup})
+	_, 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)
@@ -2653,6 +2656,17 @@ func (b *Bot) rememberSettingsMessage(ctx context.Context, userID int64, chatID
 	}
 }
 
+func clearInlineKeyboardMarkup() *InlineKeyboardMarkup {
+	return &InlineKeyboardMarkup{InlineKeyboard: [][]InlineKeyboardButton{}}
+}
+
+func editReplyMarkup(markup *InlineKeyboardMarkup) *InlineKeyboardMarkup {
+	if markup != nil {
+		return markup
+	}
+	return clearInlineKeyboardMarkup()
+}
+
 func approvalMarkup(id int64) *InlineKeyboardMarkup {
 	return &InlineKeyboardMarkup{InlineKeyboard: [][]InlineKeyboardButton{
 		{
diff --git a/internal/telegram/render_test.go b/internal/telegram/render_test.go
index 661ecb7..71967fe 100644
--- a/internal/telegram/render_test.go
+++ b/internal/telegram/render_test.go
@@ -84,6 +84,25 @@ func TestApprovalResponseForPermissions(t *testing.T) {
 	}
 }
 
+func TestEditReplyMarkupClearsInlineKeyboard(t *testing.T) {
+	markup := editReplyMarkup(nil)
+	if markup == nil {
+		t.Fatal("nil edit markup would leave Telegram buttons unchanged")
+	}
+	raw, err := json.Marshal(markup)
+	if err != nil {
+		t.Fatal(err)
+	}
+	if string(raw) != `{"inline_keyboard":[]}` {
+		t.Fatalf("clear markup JSON = %s", raw)
+	}
+
+	existing := approvalMarkup(7)
+	if editReplyMarkup(existing) != existing {
+		t.Fatal("non-nil markup should be preserved")
+	}
+}
+
 func TestParseCommand(t *testing.T) {
 	name, args, ok := parseCommand("/resume@my_bot 123")
 	if !ok || name != "resume" || len(args) != 1 || args[0] != "123" {