--- a/config/config.go
+++ b/config/config.go
@@ -8,14 +8,16 @@
 )
 
 type Config struct {
-	BotToken                   *string `yaml:"bot_token"`
-	AdminChatId                *int64  `yaml:"admin_chat_id"`
-	AdminChatTopicId           *int    `yaml:"admin_chat_topic_id"`
-	TargetChatId               *int64  `yaml:"target_chat_id"`
-	EntryMessage               string  `yaml:"entry_message"`
-	ApprovalMessage            string  `yaml:"approval_message"`
-	SendApprovalMessage        bool    `yaml:"send_approval_message"`
-	DeleteRequestAfterDecision bool    `yaml:"delete_request_after_decision"`
+	BotToken                   *string  `yaml:"bot_token"`
+	AdminChatId                *int64   `yaml:"admin_chat_id"`
+	AdminChatTopicId           *int     `yaml:"admin_chat_topic_id"`
+	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"`
 }
 
 func (c *Config) LoadConfig() error {
@@ -43,10 +45,12 @@
 		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,
+		CannedDeclineResponses:     []string{},
 	}
 
 	encoder := yaml.NewEncoder(f)
--- a/handlers/callbacks.go
+++ b//handlers/callbacks.go
@@ -39,7 +39,6 @@
 		bot.DeletePendingUser(args)
 	case "decline":
 		bot.handleDeclineRequest(query, user, userString, adminUserString)
-		bot.DeletePendingUser(args)
 	case "ban":
 		bot.showBanConfirmation(query, user)
 		bot.API.Request(api.NewCallback(query.ID, ""))
@@ -47,6 +46,19 @@
 	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 {
+			var respIdx int
+			fmt.Sscanf(parts[2], "%d", &respIdx)
+			bot.sendCannedResponse(query, user, respIdx)
+		}
+		bot.DeletePendingUser(args)
+		bot.API.Request(api.NewCallback(query.ID, ""))
+		return
 	}
 
 	if bot.Config.DeleteRequestAfterDecision {
@@ -54,6 +66,22 @@
 	}
 }
 
+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{
@@ -94,14 +122,39 @@
 		return
 	}
 
-	utils.EditMessage(bot.API, query.Message.Chat.ID, query.Message.MessageID,
-		fmt.Sprintf(AdminDeclinedMsg,
-			userString, user.From.ID, user.JoinReason, adminUserString,
-			time.Now().Format("2006-01-02 15:04:05"),
-			defaultReason,
-		),
+	messageText := fmt.Sprintf(AdminDeclinedMsg,
+		userString, user.From.ID, user.JoinReason, adminUserString,
+		time.Now().Format("2006-01-02 15:04:05"),
+		defaultReason,
 	)
 
+	edit := api.NewEditMessageText(query.Message.Chat.ID, query.Message.MessageID, messageText)
+	edit.ParseMode = api.ModeHTML
+	edit.Entities = query.Message.Entities
+
+	if len(bot.Config.CannedDeclineResponses) > 0 {
+		var rows [][]api.InlineKeyboardButton
+		for i, response := range bot.Config.CannedDeclineResponses {
+			// Clean up the response text for button display
+			snippet := strings.TrimSpace(response)
+			snippet = strings.ReplaceAll(snippet, "\n", " ")
+			// Remove multiple consecutive spaces
+			for strings.Contains(snippet, "  ") {
+				snippet = strings.ReplaceAll(snippet, "  ", " ")
+			}
+			// Truncate to 30 chars for button text
+			if len(snippet) > 30 {
+				snippet = snippet[:30] + "..."
+			}
+			btn := api.NewInlineKeyboardButtonData(snippet, fmt.Sprintf("cannedrespsel_%d_%d", user.From.ID, i))
+			rows = append(rows, []api.InlineKeyboardButton{btn})
+		}
+		keyboard := api.NewInlineKeyboardMarkup(rows...)
+		edit.ReplyMarkup = &keyboard
+	}
+
+	bot.API.Send(edit)
+
 	bot.API.Request(api.NewCallback(query.ID, "Join request declined."))
 }
 
@@ -176,12 +229,14 @@
 	userID, username, joinReason, declinedBy, declinedAt := utils.GetInfoFromMsg(repliedMsg.Text)
 
 	reason := utils.EscapeHTML(update.Message.Text)
-	if strings.HasPrefix(update.Message.Text, "+") {
-		reason = utils.EscapeHTML(update.Message.Text[1:])
+	if !strings.HasPrefix(update.Message.Text, "/") {
+		reason = utils.EscapeHTML(update.Message.Text)
 		utils.SendMessage(bot.API, userID, 0,
 			fmt.Sprintf("Your join request was declined for the following reason:\n\n%s", reason))
 	}
 
+	reason = strings.TrimPrefix(reason, "/")
+
 	utils.EditMessage(bot.API, update.Message.Chat.ID, repliedMsg.MessageID,
 		fmt.Sprintf(AdminDeclinedMsg, username, userID, joinReason, declinedBy, declinedAt, reason))
 
@@ -189,6 +244,26 @@
 	bot.API.Send(api.NewDeleteMessage(update.Message.Chat.ID, update.Message.MessageID))
 }
 
+// sendCannedResponse sends a canned decline response to the declined user.
+func (bot *Bot) sendCannedResponse(query *api.CallbackQuery, user *ExtendedChatJoinRequest, respIdx int) {
+	if respIdx < 0 || respIdx >= len(bot.Config.CannedDeclineResponses) {
+		return
+	}
+
+	reason := utils.EscapeHTML(bot.Config.CannedDeclineResponses[respIdx])
+	utils.SendMessage(bot.API, user.From.ID, 0,
+		fmt.Sprintf("Your join request was declined for the following reason:\n\n%s", reason))
+
+	// Extract user info from original message and reformat with the canned response
+	userID, username, joinReason, declinedBy, declinedAt := utils.GetInfoFromMsg(query.Message.Text)
+
+	edit := api.NewEditMessageText(query.Message.Chat.ID, query.Message.MessageID,
+		fmt.Sprintf(AdminDeclinedMsg, username, userID, joinReason, declinedBy, declinedAt, reason))
+	edit.ParseMode = api.ModeHTML
+	edit.Entities = query.Message.Entities
+	bot.API.Send(edit)
+}
+
 // parseCallbackData parses the action and user ID from a callback query's data string.
 func parseCallbackData(data string) (action string, userID int64, err error) {
 	normalized := strings.Join(strings.Split(data, "_"), " ")

--- a/handlers/handlers.go
+++ b/handlers/handlers.go
@@ -13,7 +13,7 @@
 	AdminDeclinedMsg    = "❌ Join #request declined for %s [<code>%d</code>]\n\n<b>Join reason</b>: %s\n<b>Declined by</b>: %s\n<b>Declined at</b>: %s\n<b>Declined reason</b>: %s"
 	AdminBannedMsg      = "🚫 Join #request banned for %s [<code>%d</code>]\n\n<b>Join reason</b>: %s\n<b>Banned by</b>: %s\n<b>Banned at</b>: %s\n<b>Banned until</b>: %s"
 	AdminFailedMsg      = "⚠️ Join #request failed for %s [<code>%d</code>]\n\n<b>Join reason</b>: %s\n<b>Failure reason</b>: %s"
-	defaultReason       = "(no reason provided, reply to this to set one, prepend with + to also send to user)"
+	defaultReason       = "(no reason provided, reply to this message to send one to the user, prepend with / to just set it)"
 )
 
 // Types shared by handler files
--- a/handlers/join.go
+++ b/handlers/join.go
@@ -19,6 +19,10 @@
 	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 @@
 
 // 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 {
--- a/pkg/utils/utils.go
+++ b/pkg/utils/utils.go
@@ -38,7 +38,7 @@
 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},