diff --git a/config/config.go b/config/config.go
index 45215ea..51b4d4e 100644
--- a/config/config.go
+++ b/config/config.go
@@ -14,6 +14,7 @@ type Config struct {
 	TargetChatId               *int64   `yaml:"target_chat_id"`
 	EntryMessage               string   `yaml:"entry_message"`
 	ApprovalMessage            string   `yaml:"approval_message"`
+	ReminderMessage            string   `yaml:"reminder_message"`
 	SendApprovalMessage        bool     `yaml:"send_approval_message"`
 	DeleteRequestAfterDecision bool     `yaml:"delete_request_after_decision"`
 	CannedDeclineResponses     []string `yaml:"canned_decline_responses"`
@@ -44,7 +45,8 @@ func (c *Config) CreateConfig() error {
 		AdminChatId:                Int64Ptr(0),
 		AdminChatTopicId:           IntPtr(0),
 		TargetChatId:               Int64Ptr(0),
-		EntryMessage:               "You have requested to join the group, please write a brief message explaining why you want to join.",
+		EntryMessage:               "You have requested to join the group. Please write a brief message explaining why you want to join.",
+		ReminderMessage:            "Don't forget to give a one-message response to your join request.",
 		ApprovalMessage:            "",
 		SendApprovalMessage:        false,
 		DeleteRequestAfterDecision: false,
diff --git a/handlers/callbacks.go b/handlers/callbacks.go
index 59afc85..d39bc18 100644
--- a/handlers/callbacks.go
+++ b/handlers/callbacks.go
@@ -46,6 +46,9 @@ func (bot *Bot) HandleCallbackQuery(query *api.CallbackQuery) {
 	case "banc":
 		bot.handleBanRequest(query, user, userString, adminUserString)
 		bot.DeletePendingUser(args)
+	case "remind":
+		bot.sendReminder(query, user, userString, adminUserString)
+		bot.API.Request(api.NewCallback(query.ID, "Reminder sent!"))
 	case "cannedrespsel":
 		parts := strings.Split(query.Data, "_")
 		if len(parts) >= 3 {
@@ -63,6 +66,22 @@ func (bot *Bot) HandleCallbackQuery(query *api.CallbackQuery) {
 	}
 }
 
+func (bot *Bot) sendReminder(query *api.CallbackQuery, user *ExtendedChatJoinRequest, userString, adminUserString string) {
+	utils.SendMessage(bot.API, user.From.ID, 0, bot.Config.ReminderMessage)
+
+	// Edit admin message to show reminder was sent
+	messageText := fmt.Sprintf(AdminJoinRequestMsg, userString, user.From.ID, user.JoinReason)
+	messageText += fmt.Sprintf("\n\n<b>Reminder sent by</b>: %s\n<b>Reminder sent at</b>: %s",
+		adminUserString, time.Now().Format("2006-01-02 15:04:05"))
+
+	keyboard := utils.NewApprovalKeyboard(user.From.ID)
+
+	edit := api.NewEditMessageText(query.Message.Chat.ID, query.Message.MessageID, messageText)
+	edit.ParseMode = api.ModeHTML
+	edit.ReplyMarkup = &keyboard
+	bot.API.Send(edit)
+}
+
 // handleApproveRequest approves a join request and sends an approval callback.
 func (bot *Bot) handleApproveRequest(query *api.CallbackQuery, user *ExtendedChatJoinRequest, userString, adminUserString string) {
 	r := api.ApproveChatJoinRequestConfig{
diff --git a/handlers/join.go b/handlers/join.go
index b050d11..9badd98 100644
--- a/handlers/join.go
+++ b/handlers/join.go
@@ -19,6 +19,10 @@ func (bot *Bot) HandleJoinRequestResponse(user *ExtendedChatJoinRequest, update
 	userString := utils.BuildUserString(&user.From)
 
 	keyboard := utils.NewApprovalKeyboard(user.From.ID)
+	if bot.Config.ReminderMessage != "" {
+		newButton := api.NewInlineKeyboardButtonData("Send Reminder", fmt.Sprintf("remind_%d", user.From.ID))
+		keyboard.InlineKeyboard[1] = append([]api.InlineKeyboardButton{newButton}, keyboard.InlineKeyboard[1]...)
+	}
 	utils.EditMessageWithKeyboard(bot.API, *bot.Config.AdminChatId, user.JoinRequestMessageID,
 		fmt.Sprintf(AdminJoinRequestMsg, userString, user.From.ID, user.JoinReason), &keyboard)
 
@@ -27,12 +31,24 @@ func (bot *Bot) HandleJoinRequestResponse(user *ExtendedChatJoinRequest, update
 
 // HandleJoinRequest initiates the join approval flow by sending the entry message and admin notification.
 func (bot *Bot) HandleJoinRequest(request *api.ChatJoinRequest) {
+	// Check if user already has a pending request
+	if existingUser := bot.GetPendingUser(request.From.ID); existingUser != nil {
+		utils.SendMessage(bot.API, request.From.ID, 0,
+			"You have already requested to join. Please send a single message as your join reason.")
+		return
+	}
+
 	utils.SendMessage(bot.API, request.From.ID, 0, bot.Config.EntryMessage)
 	userString := utils.BuildUserString(&request.From)
 
+	keyboard := utils.NewApprovalKeyboard(request.From.ID)
+	if bot.Config.ReminderMessage != "" {
+		newButton := api.NewInlineKeyboardButtonData("Send Reminder", fmt.Sprintf("remind_%d", request.From.ID))
+		keyboard.InlineKeyboard[1] = append([]api.InlineKeyboardButton{newButton}, keyboard.InlineKeyboard[1]...)
+	}
 	m := api.NewMessage(*bot.Config.AdminChatId,
 		fmt.Sprintf(AdminJoinRequestMsg, userString, request.From.ID, "(awaiting user response)"))
-	m.ReplyMarkup = utils.NewApprovalKeyboard(request.From.ID)
+	m.ReplyMarkup = keyboard
 	m.ParseMode = api.ModeHTML
 	m.LinkPreviewOptions = api.LinkPreviewOptions{IsDisabled: true}
 	if topic := *bot.Config.AdminChatTopicId; topic != 0 {
diff --git a/pkg/utils/utils.go b/pkg/utils/utils.go
index 1456b40..c18a452 100644
--- a/pkg/utils/utils.go
+++ b/pkg/utils/utils.go
@@ -38,7 +38,7 @@ func EscapeHTML(s string) string {
 func NewApprovalKeyboard(userID int64) api.InlineKeyboardMarkup {
 	approveBtn := api.NewInlineKeyboardButtonData("Approve", fmt.Sprintf("approve_%d", userID))
 	declineBtn := api.NewInlineKeyboardButtonData("Decline", fmt.Sprintf("decline_%d", userID))
-	banBtn := api.NewInlineKeyboardButtonData("Ban (24h)", fmt.Sprintf("ban_%d", userID))
+	banBtn := api.NewInlineKeyboardButtonData("⚠️ Ban (24h)", fmt.Sprintf("ban_%d", userID))
 	return api.NewInlineKeyboardMarkup(
 		[]api.InlineKeyboardButton{approveBtn, declineBtn},
 		[]api.InlineKeyboardButton{banBtn},