feat: schedule page SMS reminders with AI follow-up and reschedule column

- Add Text Reminder for Column button with per-column checkboxes and AI follow-up toggle (default on)
- Batch reminder endpoint resolves {firstName}, {officeName}, {appointmentDate}, {appointmentTime} from AI chat templates
- Add Reschedule for Column UI (logic TBD)
- Move Download Claim PDF for Column below Reschedule for Column
- Add reminderSms template field to AI Chat Settings with variable hints

Co-Authored-By: Claude Sonnet 4.6 <noreply@anthropic.com>

apps/Backend/src/routes/ai-settings.ts

@@ -53,8 +53,8 @@ router.put("/chat-templates", async (req: Request, res: Response): Promise<any>
   try {
     const userId = req.user?.id;
     if (!userId) return res.status(401).json({ message: "Unauthorized" });
-    const { reminderGreeting, newPatientGreeting, generalFallback, rescheduleGreeting } = req.body;
+    const { reminderGreeting, newPatientGreeting, generalFallback, rescheduleGreeting, reminderSms } = req.body;
-    await storage.saveAiChatTemplates(userId, { reminderGreeting, newPatientGreeting, generalFallback, rescheduleGreeting });
+    await storage.saveAiChatTemplates(userId, { reminderGreeting, newPatientGreeting, generalFallback, rescheduleGreeting, reminderSms });
     const updated = await storage.getAiChatTemplates(userId);
     return res.status(200).json(updated);
   } catch (err) {

apps/Backend/src/routes/twilio.ts

@@ -1,6 +1,7 @@
 import express, { Request, Response } from "express";
 import twilio from "twilio";
 import { storage } from "../storage";
+import { prisma as db } from "@repo/db/client";
 import { getHandoff, setHandoff, resetConversation, startNewPatientConversation, startRescheduleConversation, getAfterHoursHandoff, setAfterHoursHandoff } from "../ai/aiHandoffStore";
 
 const router = express.Router();
@@ -97,7 +98,10 @@ router.post("/send-sms", async (req: Request, res: Response): Promise<any> => {
         await startNewPatientConversation(userId, pid);
       } else if (startFlow === "reschedule") {
         await startRescheduleConversation(userId, pid);
+      } else if (startFlow === "no_follow_up") {
+        // AI follow-up disabled — leave existing stage untouched
       } else {
+        // "reminder" or unspecified → start reminder AI flow
         await resetConversation(userId, pid);
       }
     }
@@ -108,6 +112,116 @@ router.post("/send-sms", async (req: Request, res: Response): Promise<any> => {
   }
 });
 
+// POST /api/twilio/send-reminders-batch
+router.post("/send-reminders-batch", async (req: Request, res: Response): Promise<any> => {
+  try {
+    const userId = req.user?.id;
+    if (!userId) return res.status(401).json({ message: "Unauthorized" });
+
+    const { date, staffIds, aiFollowUp = true } = req.body as {
+      date: string;
+      staffIds: number[];
+      aiFollowUp?: boolean;
+    };
+    if (!date || !Array.isArray(staffIds) || staffIds.length === 0) {
+      return res.status(400).json({ message: "date and staffIds are required" });
+    }
+
+    const settings = await storage.getTwilioSettings(userId);
+    if (!settings) {
+      return res.status(400).json({ message: "Twilio is not configured. Please add your Twilio credentials in Settings." });
+    }
+
+    // Resolve office name and reminder SMS template
+    const officeContact = await storage.getOfficeContact(userId);
+    const officeName = (officeContact as any)?.officeName?.trim() || "";
+    const chatTemplates = await storage.getAiChatTemplates(userId);
+
+    const DEFAULT_REMINDER_SMS =
+      "Hi {firstName}, this is a reminder from {officeName}. You have an appointment on {appointmentDate} at {appointmentTime}. Please reply YES to confirm or NO to reschedule. Thank you!";
+    const templateBody = chatTemplates.reminderSms?.trim() || DEFAULT_REMINDER_SMS;
+
+    // Fetch appointments for the selected staff columns on the given date
+    const dayStart = new Date(date);
+    dayStart.setUTCHours(0, 0, 0, 0);
+    const dayEnd = new Date(date);
+    dayEnd.setUTCHours(23, 59, 59, 999);
+
+    const appointments = await db.appointment.findMany({
+      where: {
+        staffId: { in: staffIds },
+        date: { gte: dayStart, lte: dayEnd },
+        status: { not: "cancelled" },
+        patient: { userId },
+      },
+      include: {
+        patient: { select: { id: true, firstName: true, phone: true } },
+      },
+      orderBy: { startTime: "asc" },
+    });
+
+    // Format a date string as "May 9, 2026"
+    const months = ["January","February","March","April","May","June","July","August","September","October","November","December"];
+    const formatApptDate = (d: Date | string) => {
+      const dt = new Date(d);
+      return `${months[dt.getUTCMonth()]} ${dt.getUTCDate()}, ${dt.getUTCFullYear()}`;
+    };
+
+    const client = getTwilioClient(settings.accountSid, settings.authToken);
+    let sent = 0;
+    let skipped = 0;
+
+    // Deduplicate by patientId — send at most one reminder per patient per run
+    const seen = new Set<number>();
+
+    for (const appt of appointments) {
+      const patient = appt.patient;
+      if (!patient?.phone || seen.has(patient.id)) { skipped++; continue; }
+      seen.add(patient.id);
+
+      const apptDate      = formatApptDate(appt.date);
+      const apptTime      = typeof appt.startTime === "string"
+        ? appt.startTime.substring(0, 5)
+        : String(appt.startTime);
+
+      const message = templateBody
+        .replace(/\{firstName\}/g,       patient.firstName ?? "")
+        .replace(/\{officeName\}/g,      officeName)
+        .replace(/\{appointmentDate\}/g, apptDate)
+        .replace(/\{appointmentTime\}/g, apptTime)
+        .replace(/\{date\}/g,            apptDate)
+        .replace(/\{time\}/g,            apptTime);
+
+      try {
+        const twilioMsg = await client.messages.create({
+          body: message,
+          from: settings.phoneNumber,
+          to: patient.phone,
+        });
+        await storage.createCommunication({
+          patientId: patient.id,
+          userId,
+          channel: "sms",
+          direction: "outbound",
+          status: "sent",
+          body: message,
+          twilioSid: twilioMsg.sid,
+        });
+        if (aiFollowUp) {
+          await resetConversation(userId, patient.id);
+        }
+        sent++;
+      } catch {
+        skipped++;
+      }
+    }
+
+    return res.status(200).json({ sent, skipped });
+  } catch (err: any) {
+    return res.status(500).json({ error: err.message || "Failed to send reminders" });
+  }
+});
+
 // GET /api/twilio/templates
 router.get("/templates", async (req: Request, res: Response): Promise<any> => {
   try {

apps/Backend/src/storage/twilio-storage.ts

@@ -67,10 +67,11 @@ export const twilioStorage = {
       newPatientGreeting:  all["_ai_chat_new_patient_greeting"] ?? "",
       generalFallback:     all["_ai_chat_general_fallback"]     ?? "",
       rescheduleGreeting:  all["_ai_chat_reschedule_greeting"]  ?? "",
+      reminderSms:         all["_ai_chat_reminder_sms"]         ?? "",
     };
   },
 
-  async saveAiChatTemplates(userId: number, templates: { reminderGreeting?: string; newPatientGreeting?: string; generalFallback?: string; rescheduleGreeting?: string }) {
+  async saveAiChatTemplates(userId: number, templates: { reminderGreeting?: string; newPatientGreeting?: string; generalFallback?: string; rescheduleGreeting?: string; reminderSms?: string }) {
     const settings = await db.twilioSettings.findUnique({ where: { userId } });
     const existing = (settings?.templates as Record<string, string>) || {};
     const updated: Record<string, string> = { ...existing };
@@ -78,6 +79,7 @@ export const twilioStorage = {
     if (templates.newPatientGreeting !== undefined) updated["_ai_chat_new_patient_greeting"]  = templates.newPatientGreeting;
     if (templates.generalFallback    !== undefined) updated["_ai_chat_general_fallback"]      = templates.generalFallback;
     if (templates.rescheduleGreeting !== undefined) updated["_ai_chat_reschedule_greeting"]   = templates.rescheduleGreeting;
+    if (templates.reminderSms        !== undefined) updated["_ai_chat_reminder_sms"]          = templates.reminderSms;
     return db.twilioSettings.upsert({
       where:  { userId },
       update: { templates: updated },

apps/Frontend/src/components/settings/ai-chat-templates-card.tsx

@@ -12,6 +12,7 @@ type AiChatTemplates = {
   newPatientGreeting: string;
   generalFallback: string;
   rescheduleGreeting: string;
+  reminderSms: string;
 };
 
 type OfficeContact = {
@@ -19,6 +20,8 @@ type OfficeContact = {
 };
 
 const DEFAULTS = {
+  reminderSms:
+    "Hi {firstName}, this is a reminder from {officeName}. You have an appointment on {appointmentDate} at {appointmentTime}. Please reply YES to confirm or NO to reschedule. Thank you!",
   reminderGreeting:
     "Hi! My name is Lisa, the dedicated AI assistant at {officeName}. I can confirm or reschedule your appointment and answer general questions 24/7. How can I help you today?",
   newPatientGreeting:
@@ -36,6 +39,7 @@ function preview(text: string, officeName: string) {
 export function AiChatTemplatesCard() {
   const { toast } = useToast();
 
+  const [reminderSms,        setReminderSms]        = useState(DEFAULTS.reminderSms);
   const [reminderGreeting,   setReminderGreeting]   = useState(DEFAULTS.reminderGreeting);
   const [newPatientGreeting, setNewPatientGreeting] = useState(DEFAULTS.newPatientGreeting);
   const [generalFallback,    setGeneralFallback]    = useState(DEFAULTS.generalFallback);
@@ -67,6 +71,7 @@ export function AiChatTemplatesCard() {
   useEffect(() => {
     if (templates && !initialized.current) {
       initialized.current = true;
+      setReminderSms(templates.reminderSms               || DEFAULTS.reminderSms);
       setReminderGreeting(templates.reminderGreeting     || DEFAULTS.reminderGreeting);
       setNewPatientGreeting(templates.newPatientGreeting || DEFAULTS.newPatientGreeting);
       setGeneralFallback(templates.generalFallback       || DEFAULTS.generalFallback);
@@ -95,6 +100,7 @@ export function AiChatTemplatesCard() {
   const handleSubmit = (e: React.FormEvent) => {
     e.preventDefault();
     saveMutation.mutate({
+      reminderSms:        reminderSms.trim()         || DEFAULTS.reminderSms,
       reminderGreeting:   reminderGreeting.trim()   || DEFAULTS.reminderGreeting,
       newPatientGreeting: newPatientGreeting.trim()  || DEFAULTS.newPatientGreeting,
       generalFallback:    generalFallback.trim()     || DEFAULTS.generalFallback,
@@ -105,6 +111,15 @@ export function AiChatTemplatesCard() {
   const officeName = officeContact?.officeName?.trim() || "";
 
   const templates_list = [
+    {
+      key: "reminderSms" as const,
+      icon: <CalendarCheck className="h-4 w-4 text-primary" />,
+      label: "Reminder SMS Text",
+      description: "Outgoing text sent from the Schedule page. Supports: {firstName}, {officeName}, {appointmentDate}, {appointmentTime}.",
+      value: reminderSms,
+      onChange: setReminderSms,
+      placeholder: DEFAULTS.reminderSms,
+    },
     {
       key: "reminder" as const,
       icon: <CalendarCheck className="h-4 w-4 text-primary" />,
@@ -152,9 +167,12 @@ export function AiChatTemplatesCard() {
           <h3 className="text-lg font-semibold">AI Chat Templates</h3>
         </div>
         <p className="text-sm text-muted-foreground">
-          Customize how your AI assistant introduces itself and responds to patients. Use{" "}
+          Customize the reminder SMS and AI reply templates. Available variables:{" "}
+          <code className="bg-muted px-1 py-0.5 rounded text-xs font-mono">{"{firstName}"}</code>{" "}
           <code className="bg-muted px-1 py-0.5 rounded text-xs font-mono">{"{officeName}"}</code>{" "}
-          as a placeholder — it will be replaced automatically with your dental office name.
+          <code className="bg-muted px-1 py-0.5 rounded text-xs font-mono">{"{appointmentDate}"}</code>{" "}
+          <code className="bg-muted px-1 py-0.5 rounded text-xs font-mono">{"{appointmentTime}"}</code>{" "}
+          — replaced automatically when reminders are sent.
         </p>
 
         {/* Office name hint */}
@@ -208,6 +226,7 @@ export function AiChatTemplatesCard() {
                 variant="ghost"
                 className="text-xs text-muted-foreground"
                 onClick={() => {
+                  setReminderSms(DEFAULTS.reminderSms);
                   setReminderGreeting(DEFAULTS.reminderGreeting);
                   setNewPatientGreeting(DEFAULTS.newPatientGreeting);
                   setGeneralFallback(DEFAULTS.generalFallback);

apps/Frontend/src/pages/appointments-page.tsx

@@ -158,6 +158,9 @@ export default function AppointmentsPage() {
   const [selectedClaimColumns, setSelectedClaimColumns] = useState<Set<number>>(new Set());
   const [isClaimingColumn, setIsClaimingColumn] = useState(false);
   const [selectedReminderColumns, setSelectedReminderColumns] = useState<Set<number>>(new Set());
+  const [isSendingReminders, setIsSendingReminders] = useState(false);
+  const [reminderAiFollowUp, setReminderAiFollowUp] = useState(true);
+  const [selectedRescheduleColumns, setSelectedRescheduleColumns] = useState<Set<number>>(new Set());
   const [selectedDownloadPdfColumns, setSelectedDownloadPdfColumns] = useState<Set<number>>(new Set());
   const [isDownloadingClaimPdfs, setIsDownloadingClaimPdfs] = useState(false);
   const [columnLabels, setColumnLabels] = useState<Record<string, string>>({});
@@ -187,6 +190,15 @@ export default function AppointmentsPage() {
     });
   };
 
+  const toggleRescheduleColumn = (staffId: number) => {
+    setSelectedRescheduleColumns((prev) => {
+      const next = new Set(prev);
+      if (next.has(staffId)) next.delete(staffId);
+      else next.add(staffId);
+      return next;
+    });
+  };
+
   const toggleDownloadPdfColumn = (staffId: number) => {
     setSelectedDownloadPdfColumns((prev) => {
       const next = new Set(prev);
@@ -1202,6 +1214,27 @@ export default function AppointmentsPage() {
     }
   };
 
+  const handleSendRemindersForColumn = async () => {
+    if (!user || selectedReminderColumns.size === 0) return;
+    setIsSendingReminders(true);
+    try {
+      const res = await apiRequest("POST", "/api/twilio/send-reminders-batch", {
+        date: formattedSelectedDate,
+        staffIds: Array.from(selectedReminderColumns),
+        aiFollowUp: reminderAiFollowUp,
+      });
+      const { sent, skipped } = await res.json();
+      toast({
+        title: "Text Reminders Sent",
+        description: `Sent ${sent} reminder${sent !== 1 ? "s" : ""}${skipped > 0 ? `, skipped ${skipped} (no phone)` : ""}.`,
+      });
+    } catch (err: any) {
+      toast({ title: "Failed to Send Reminders", description: err?.message ?? String(err), variant: "destructive" });
+    } finally {
+      setIsSendingReminders(false);
+    }
+  };
+
   const handleDownloadClaimPdfs = async () => {
     if (!user || selectedDownloadPdfColumns.size === 0) return;
     const staffIdsParam = Array.from(selectedDownloadPdfColumns).join(",");
@@ -1349,10 +1382,21 @@ export default function AppointmentsPage() {
             {/* Text Reminder for Column section */}
             <div className="flex items-center gap-2 border rounded-md px-3 py-2 bg-white shadow-sm">
               <Button
-                disabled={true}
+                onClick={() => handleSendRemindersForColumn()}
+                disabled={isLoading || isSendingReminders || selectedReminderColumns.size === 0}
                 size="sm"
               >
-                Text Reminder for Column
+                {isSendingReminders ? (
+                  <>
+                    <LoaderCircleIcon className="h-4 w-4 mr-1 animate-spin" />
+                    Sending...
+                  </>
+                ) : (
+                  <>
+                    <MessageSquare className="h-4 w-4 mr-1" />
+                    Text Reminder for Column
+                  </>
+                )}
               </Button>
               {staffMembers.map((staff, index) => (
                 <label
@@ -1370,6 +1414,46 @@ export default function AppointmentsPage() {
                   </span>
                 </label>
               ))}
+              <div className="flex items-center gap-1.5 ml-2 pl-2 border-l border-gray-200">
+                <button
+                  type="button"
+                  role="switch"
+                  aria-checked={reminderAiFollowUp}
+                  onClick={() => setReminderAiFollowUp((v) => !v)}
+                  className={`relative inline-flex h-5 w-9 shrink-0 cursor-pointer rounded-full border-2 border-transparent transition-colors focus:outline-none ${reminderAiFollowUp ? "bg-teal-600" : "bg-gray-300"}`}
+                >
+                  <span
+                    className={`pointer-events-none inline-block h-4 w-4 rounded-full bg-white shadow transform transition-transform ${reminderAiFollowUp ? "translate-x-4" : "translate-x-0"}`}
+                  />
+                </button>
+                <span className="text-xs text-gray-600 whitespace-nowrap">AI follow up</span>
+              </div>
+            </div>
+
+            {/* Reschedule for Column section */}
+            <div className="flex items-center gap-2 border rounded-md px-3 py-2 bg-white shadow-sm">
+              <Button
+                disabled={true}
+                size="sm"
+              >
+                Reschedule for Column
+              </Button>
+              {staffMembers.map((staff, index) => (
+                <label
+                  key={staff.id}
+                  className="flex items-center gap-1 cursor-pointer select-none"
+                >
+                  <input
+                    type="checkbox"
+                    className="w-4 h-4 rounded border-gray-400 accent-teal-600"
+                    checked={selectedRescheduleColumns.has(Number(staff.id))}
+                    onChange={() => toggleRescheduleColumn(Number(staff.id))}
+                  />
+                  <span className="text-sm font-medium">
+                    {columnLabels[String(staff.id)] ?? String.fromCharCode(65 + index)}
+                  </span>
+                </label>
+              ))}
             </div>
 
             {/* Download Claim PDF for Column section */}