fix yesterdays schedule blocking todays

When adaptive timing shifts a late-night dose past midnight (e.g. 23:00
→ 00:42), the scheduler would create a new pending schedule on the next
day even if the dose was already taken. The proximity window was too
narrow to match the take log against the shifted time.

- Skip creating schedules for doses already taken/skipped (checks
  today + yesterday logs against base_time)
- Fix midnight wraparound in proximity check for should_send_nag
- Display base_time (actual dose time) in reminders instead of the
  internal adjusted_time

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

README.md

@@ -1,14 +1,14 @@
 # Synculous
 
-A routine and medication management app designed as a prosthetic for executive function. Built for people with ADHD.
+A comprehensive routine and medication management app designed as a prosthetic for executive function. Built for people with ADHD.
 
-The app externalizes the things ADHD impairs — time awareness, sequence memory, task initiation, and emotional regulation around failure — into a guided, sequential interface with immediate feedback and zero shame.
+The app externalizes the things ADHD impairs — time awareness, sequence memory, task initiation, and emotional regulation around failure — into a guided, sequential interface with immediate feedback and zero shame. It combines structured routines, intelligent medication tracking, AI-powered safety systems, and peer accountability features into one unified platform.
 
 ## Architecture
 
 ```
 synculous/
-├── synculous-client/       # Next.js 16 frontend (React, Tailwind)
+├── synculous-client/           # Next.js frontend (React, Tailwind)
 ├── api/                        # Flask REST API
 │   ├── main.py                 # App entry point, auth routes
 │   └── routes/                 # Domain route modules
@@ -19,28 +19,49 @@ synculous/
 │       ├── routine_steps_extended.py     # Step instructions, types, media
 │       ├── routine_tags.py         # Tagging system
 │       ├── medications.py          # Medication scheduling + adherence
+│       ├── adaptive_meds.py        # Adaptive medication timing (learning)
+│       ├── tasks.py                # One-off tasks/appointments CRUD
+│       ├── ai.py                   # AI-powered step generation
 │       ├── preferences.py          # User settings + timezone
 │       ├── notifications.py        # Web push subscriptions
 │       ├── rewards.py              # Variable reward system
-│       └── victories.py        # Achievement detection
+│       ├── victories.py            # Achievement detection
+│       └── snitch.py               # Peer accountability contacts + notifications
 ├── core/                       # Shared business logic
 │   ├── postgres.py             # Generic PostgreSQL CRUD
 │   ├── auth.py                 # JWT + bcrypt authentication
 │   ├── users.py                # User management
 │   ├── routines.py             # Routine/session/streak logic
-│   ├── tz.py               # Timezone-aware date/time helpers
+│   ├── stats.py                # Statistics calculations (completion rates, streaks)
+│   ├── snitch.py               # Snitch trigger logic + notification delivery
+│   ├── adaptive_meds.py        # Adaptive medication timing logic
+│   ├── tz.py                   # Timezone-aware date/time helpers (IANA + offset)
 │   └── notifications.py        # Multi-channel notifications
 ├── scheduler/
 │   └── daemon.py               # Background polling for reminders
-├── bot/                    # Discord bot (optional)
+├── bot/                        # Discord bot with knowledge RAG
-├── ai/                     # LLM parser for natural language commands
+│   ├── bot.py                  # Bot entry point + session management
+│   ├── command_registry.py     # Module-based command routing
+│   ├── commands/               # Command modules
+│   │   ├── routines.py         # /routine commands
+│   │   ├── medications.py      # /med, /take, /skip commands
+│   │   ├── tasks.py            # /task commands (one-off tasks/appointments)
+│   │   └── knowledge.py        # /ask command (jury-filtered RAG)
+│   └── hooks.py                # Event listeners
+├── ai/                         # LLM-powered features
+│   ├── parser.py               # OpenRouter API client
+│   ├── jury_council.py         # 5-juror safety filtration system
+│   ├── ai_config.json          # Model + prompt configuration
+│   └── (optional) RAG embeddings
 ├── config/
 │   ├── schema.sql              # Database schema
 │   ├── seed_templates.sql      # 12 premade ADHD-designed routine templates
 │   ├── seed_rewards.sql        # Variable reward pool
 │   └── .env.example            # Environment template
+├── diagrams/                   # Architecture diagrams (Mermaid)
 ├── docker-compose.yml
-└── Dockerfile
+├── Dockerfile
+└── tests/
 ```
 
 ## Quick Start
@@ -49,10 +70,10 @@ synculous/
 # Copy environment config
 cp config/.env.example config/.env
 
-# Edit with your values
+# Edit with your values (at minimum: DB_PASS, JWT_SECRET, optionally DISCORD_BOT_TOKEN, OPENROUTER_API_KEY)
 nano config/.env
 
-# Start everything
+# Start everything (db, api, scheduler, optional bot, frontend client)
 docker-compose up
 ```
 
@@ -61,20 +82,23 @@ This starts five services:
 | Service | Port | Description |
 |---------|------|-------------|
 | `db` | 5432 | PostgreSQL 16 with schema + seed data |
-| `app` | 8080 | Flask API |
+| `app` | 8010 | Flask API (internal: 5000) |
 | `scheduler` | — | Background daemon for medication/routine reminders |
-| `bot` | — | Discord bot (optional, needs `DISCORD_BOT_TOKEN`) |
+| `bot` | — | Discord bot with commands and knowledge RAG (optional, needs `DISCORD_BOT_TOKEN`) |
-| `client` | 3000 | Next.js frontend |
+| `client` | 3001 | Next.js frontend (internal: 3000) |
 
 ## Features
 
-### Routines
+### Routines & Sessions
 - Create routines with ordered steps (4-7 steps recommended)
 - Run sessions with a guided, one-step-at-a-time focus interface
 - Complete, skip, pause, resume, or cancel sessions
 - Swipe gestures for step completion on mobile
 - Per-step timing with visual countdown
 - Animated celebration screen on completion with streak stats and variable rewards
+- Every-N-day frequency option for routines
+- Tagging system for organizing routines by category
+- Session notes for logging context or blockers
 
 ### Premade Templates
 12 ADHD-designed templates ship out of the box, seeded from `config/seed_templates.sql`:
@@ -96,13 +120,44 @@ This starts five services:
 
 All templates follow the design framework: two-minute-rule entry points, concrete instructions, zero-shame language, 4-6 steps max.
 
+### One-Off Tasks & Appointments
+- Create standalone tasks and appointments outside of routines
+- Scheduled date/time with optional reminders
+- Quick-complete action for fast check-off
+- Tasks appear on the routines timeline for a unified daily view
+- AI-powered task composition via bot and web client
+- Natural language date parsing in bot commands
+
+### AI-Powered Step Generation
+- Generate ADHD-friendly routine steps from a plain-language goal description
+- Uses OpenRouter LLM to produce 2-minute-rule-compliant steps
+- Each step includes name and estimated duration
+- Available via API endpoint and integrated into the web client's routine creation flow
+
 ### Medications
-- Scheduling: daily, twice daily, specific days, every N days, as-needed (PRN)
+- Scheduling: daily, twice daily, specific days, every N days, as-needed (PRN); batch-schedule multiple meds at once
 - "Today's meds" view with cross-midnight lookahead (late night + early morning)
 - Take, skip, snooze actions with logging
 - Adherence tracking and statistics
 - Refill tracking with low-quantity alerts
 - Background reminders via the scheduler daemon
+- Medication editing (update name, dose, schedule, refill count)
+- Web push and Discord notifications for doses
+
+#### Adaptive Medication Timing
+- Machine-learning-based timing predictions based on user adherence patterns
+- System learns when you're most likely to take meds
+- Automatic reminder optimization (fewer false-positive reminders)
+- Override and manual timing adjustments always available
+- Useful for people with irregular schedules
+
+### Peer Accountability: "Snitch" Feature
+- Designate trusted contacts to receive medication adherence notifications
+- Contacts don't need an account or login
+- Granular privacy controls: users choose *what* to share (meds, streaks, notes)
+- Contacts receive weekly summaries or real-time alerts for missed doses
+- Based on research showing peer accountability improves adherence
+- Optional consent-based consent flow for contact approvals
 
 ### Streaks and Stats
 - Per-routine streak tracking (current + longest)
@@ -116,36 +171,97 @@ All templates follow the design framework: two-minute-rule entry points, concret
 - Random reward on routine completion (post-completion only, never mid-routine)
 - Reward history tracking per user
 - Common and rare rarity tiers
+- Designed to leverage variable-ratio reinforcement schedules
 
 ### Notifications
-- Web push notifications via VAPID
+- Web push notifications via VAPID (in-browser)
-- Discord webhooks
+- Discord webhooks (for bot mentions)
-- ntfy support
+- Discord DMs (for sensitive notifications like "snitch" alerts)
-- Scheduled reminders for medications and routines
+- ntfy support (for self-hosted push)
+- Timezone-aware scheduled reminders for medications and routines
 
-### Timezone Support
+### Timezone Support (Dual-Path)
-All date/time operations respect the user's local timezone:
+All date/time operations respect the user's local timezone via two mechanisms:
-- The frontend sends `X-Timezone-Offset` with every API request
+
-- The timezone offset is also persisted to `user_preferences` for background jobs
+**In request context:**
-- Streaks, "today's meds," weekly stats, and reminders all use the user's local date
+- The frontend sends `X-Timezone-Name` (IANA standard, e.g., "America/New_York") or `X-Timezone-Offset` header
-- The scheduler daemon looks up each user's stored offset for reminder timing
+- Handlers use these headers for real-time API operations
+
+**In background jobs (scheduler daemon):**
+- Timezone is stored in `user_preferences.timezone_name` (IANA format)
+- Scheduler retrieves stored timezone for each user
+- Falls back to numeric offset, then UTC if name is unavailable
+- Enables accurate reminder delivery even if user's browser context is offline
+
+**Result:** Streaks, "today's meds," weekly stats, and reminders all use the user's local date.
+
+### Authentication & Session Persistence
+- JWT access tokens (1-hour expiry) + optional long-lived refresh tokens (30 days)
+- "Trust this device" option on login issues a refresh token for seamless re-auth
+- Bot session caching with persistent pickle storage across restarts
 
 ### User Preferences
 - Sound effects (default off — habituation risk)
 - Haptic feedback (default on)
 - Launch screen toggle
 - Celebration style
-- Timezone offset (auto-synced from browser)
+- Timezone (IANA name + numeric offset, auto-synced from browser)
+- Discord presence indicator toggle (shows online/offline in Discord)
+
+### Discord Bot Integration
+Full-featured Discord bot for managing routines and medications without opening the app:
+
+#### Bot Commands
+- `/routine list` — List all routines
+- `/routine start <name>` — Start a routine session (guided steps in Discord thread)
+- `/routine stats <name>` — View streak and completion stats
+- `/med today` — Show today's medications with status
+- `/med take <med_name>` — Log a dose as taken
+- `/med skip <med_name>` — Log a dose as skipped
+- `/task add <description>` — Create a one-off task (supports natural language dates)
+- `/task list` — Show upcoming tasks
+- `/task done <name>` — Mark a task as complete
+- `/ask <question>` — Query the knowledge base with jury-filtered safety checks
+- Discord presence automatically shows your routine/meditation status
+
+#### Jury Council Safety System
+The `/ask` command uses a sophisticated 5-juror safety filtration pipeline:
+
+**Two-stage process:**
+1. **Question Generator** (Qwen3 Nitro, fallback to Qwen3-235B): Expands user query into 2-3 precise search questions
+2. **Jury Council** (5 parallel jurors, 100% consensus required): Each juror evaluates questions from a distinct safety lens
+
+**Juror Roles:**
+- **Safety:** Would answering cause harm? Evaluates crisis risk (C-SSRS framework), self-harm methods, lethal means
+- **Empathy:** Is this emotionally appropriate for someone in distress? Checks for deceptive empathy, harmful validation, stigmatizing language
+- **Intent:** Is this benign? Detects jailbreaks, social engineering, prompt injection, method-seeking disguised as education
+- **Clarity:** Is the question retrievable? Checks if the question is specific enough to get meaningful results from the knowledge base
+- **Ethics:** Within bounds for an informational AI? Blocks diagnosis, treatment planning, medication advice, scope violations, deceptive role-play
+
+**Safety model:** Questions only approved if ALL 5 jurors vote yes. Any juror error = fail closed. Crisis indicators trigger immediate resource redirection (988, Crisis Text Line, etc.) instead of RAG answers.
+
+This system makes it possible to serve help-seeking users asking about self-harm coping strategies, suicidal ideation management, and DBT skills while firmly rejecting harmful intent (method-seeking, glorification, extraction attempts).
+
+### Knowledge Base & RAG
+- Embeddings-based retrieval of ADHD, DBT, and mental health educational content
+- Multi-book support with user-selectable knowledge bases
+- Jury-filtered questions for safety
+- LLM-powered intent classification routes general questions to the knowledge base automatically
+- Multi-query retrieval with deduplication for better coverage
+- DBT advice evaluation mode (checks advice against DBT principles)
+- Discord bot `/ask` command uses RAG with jury council checks
+- Extensible knowledge source (can add more documents)
 
 ## API Overview
 
-All endpoints require `Authorization: Bearer <token>` except `/api/register` and `/api/login`.
+All endpoints require `Authorization: Bearer <token>` except `/api/register`, `/api/login`, and `/api/refresh`.
 
 ### Auth
 | Method | Endpoint | Description |
 |--------|----------|-------------|
 | POST | `/api/register` | Create account |
-| POST | `/api/login` | Get JWT token |
+| POST | `/api/login` | Get JWT token (optionally with refresh token via `trust_device`) |
+| POST | `/api/refresh` | Exchange refresh token for new access token |
 
 ### Routines
 | Method | Endpoint | Description |
@@ -170,6 +286,7 @@ All endpoints require `Authorization: Bearer <token>` except `/api/register` and
 | POST | `/api/sessions/:id/resume` | Resume session |
 | POST | `/api/sessions/:id/cancel` | Cancel session |
 | POST | `/api/sessions/:id/abort` | Abort with reason |
+| POST | `/api/sessions/:id/note` | Add session note |
 
 ### Medications
 | Method | Endpoint | Description |
@@ -182,6 +299,41 @@ All endpoints require `Authorization: Bearer <token>` except `/api/register` and
 | GET | `/api/medications/adherence` | Adherence stats |
 | GET | `/api/medications/refills-due` | Refills due soon |
 
+### Adaptive Medications
+| Method | Endpoint | Description |
+|--------|----------|-------------|
+| GET | `/api/adaptive-meds/:id` | Get adaptive timing data for a medication |
+| PUT | `/api/adaptive-meds/:id` | Update adaptive timing preferences |
+| POST | `/api/adaptive-meds/:id/reset` | Reset adaptive learning and return to default schedule |
+| GET | `/api/adaptive-meds/stats` | View adaptive timing effectiveness stats |
+
+### Snitch (Peer Accountability)
+| Method | Endpoint | Description |
+|--------|----------|-------------|
+| GET | `/api/snitch/contacts` | List designated accountability contacts |
+| POST | `/api/snitch/contacts` | Add a new contact (generates invite link) |
+| PUT | `/api/snitch/contacts/:id` | Update contact (name, shared info, frequency) |
+| DELETE | `/api/snitch/contacts/:id` | Remove a contact |
+| POST | `/api/snitch/contacts/:id/resend-invite` | Resend contact invite link |
+| GET | `/api/snitch/contacts/:id/consent` | Get contact's consent status |
+| POST | `/api/snitch/contacts/:id/consent` | Contact accepts or declines sharing |
+| GET | `/api/snitch/history` | View recent alerts sent to contacts |
+| POST | `/api/snitch/test-send` | Send test alert to a contact |
+
+### Tasks
+| Method | Endpoint | Description |
+|--------|----------|-------------|
+| GET | `/api/tasks` | List user's tasks |
+| POST | `/api/tasks` | Create a task |
+| PUT | `/api/tasks/:id` | Update a task |
+| DELETE | `/api/tasks/:id` | Delete a task |
+| POST | `/api/tasks/:id/complete` | Mark task as complete |
+
+### AI
+| Method | Endpoint | Description |
+|--------|----------|-------------|
+| POST | `/api/ai/generate-steps` | Generate ADHD-friendly routine steps from a goal description |
+
 ### Stats
 | Method | Endpoint | Description |
 |--------|----------|-------------|
@@ -191,37 +343,99 @@ All endpoints require `Authorization: Bearer <token>` except `/api/register` and
 | GET | `/api/routines/weekly-summary` | Weekly progress |
 | GET | `/api/victories` | Achievement detection |
 
-### Templates, Tags, Rewards, Preferences
+### Templates, Tags, Rewards, Preferences, Notifications
 | Method | Endpoint | Description |
 |--------|----------|-------------|
 | GET | `/api/templates` | List available templates |
 | POST | `/api/templates/:id/clone` | Clone template to user's routines |
-| GET/PUT | `/api/preferences` | User settings |
+| GET/PUT | `/api/preferences` | User settings and timezone |
 | GET | `/api/rewards/random` | Random completion reward |
+| POST | `/api/notifications/subscribe` | Subscribe to web push notifications (VAPID) |
+| POST | `/api/notifications/unsubscribe` | Unsubscribe from push notifications |
 
 ## Environment Variables
 
-| Variable | Description |
+| Variable | Required | Description |
-|----------|-------------|
+|----------|----------|-------------|
-| `DB_HOST` | PostgreSQL host |
+| `DB_HOST` | Yes | PostgreSQL host (default: `db` in Docker) |
-| `DB_PORT` | PostgreSQL port |
+| `DB_PORT` | Yes | PostgreSQL port (default: `5432`) |
-| `DB_NAME` | Database name |
+| `DB_NAME` | Yes | Database name (default: `app`) |
-| `DB_USER` | Database user |
+| `DB_USER` | Yes | Database user (default: `app`) |
-| `DB_PASS` | Database password |
+| `DB_PASS` | Yes | Database password |
-| `JWT_SECRET` | JWT signing secret |
+| `JWT_SECRET` | Yes | JWT signing secret (generate a random string, min 32 chars) |
-| `DISCORD_BOT_TOKEN` | Discord bot token (optional) |
+| `DISCORD_BOT_TOKEN` | No | Discord bot token (if running Discord bot) |
-| `API_URL` | API URL for bot (default: `http://app:5000`) |
+| `OPENROUTER_API_KEY` | No | OpenRouter API key (if using jury council RAG features) |
-| `OPENROUTER_API_KEY` | OpenRouter API key (for AI parser) |
+| `API_URL` | No | API URL for bot (default: `http://app:5000` in Docker) |
-| `POLL_INTERVAL` | Scheduler poll interval in seconds (default: 60) |
+| `POLL_INTERVAL` | No | Scheduler poll interval in seconds (default: `60`) |
+| `VAPID_PUBLIC_KEY` | No | VAPID public key for web push notifications |
+| `VAPID_PRIVATE_KEY` | No | VAPID private key for web push notifications |
 
 ## Design Framework
 
-Synculous follows a documented design framework based on research from 9 books on behavior design, cognitive psychology, and ADHD. The three core principles:
+Synculous follows a documented design framework based on research from 9 books on behavior design, cognitive psychology, and ADHD. The core principles inform every feature:
 
+### Core Principles
 1. **Immediate Feedback** — Visual state change on tap in <0.1s. Per-step completion signals. Post-routine celebration.
 2. **One Thing at a Time** — Current step visually dominant. No decisions during execution. 4-7 steps max per routine.
 3. **Zero Shame** — No failure language. Streaks as identity markers, not performance metrics. Non-punitive everywhere.
 
+### Behavioral Foundations
+- **Two-Minute Rule Entry Points** — Every routine starts with something achievable in under 2 minutes (lower activation energy)
+- **Variable Reward Scheduling** — Random rewards on completion leverage variable-ratio reinforcement (proven for habit building)
+- **Streak-Based Identity** — Streaks build intrinsic motivation by making completion a visible, accumulating identity signal
+- **Peer Accountability** — "Snitch" contacts provide external accountability without shame (research shows this improves adherence)
+- **Adaptive Timing** — System learns your natural rhythm and optimizes reminders based on your actual behavior (reduces cognitive load)
+
+### Safety & Ethics
+- **Jury Council** — 5-juror consensus model for AI safety ensures content is appropriate for emotionally vulnerable users
+- **Crisis Awareness** — System detects crisis indicators and redirects to professional resources (988, Crisis Text Line) rather than generic psychoeducation
+- **Transparent Limitations** — All system messages clarify "this is educational, not treatment" and encourage professional care
+- **User Agency** — All adaptive and automated features can be overridden; manual controls are always available
+
+## Development & Testing
+
+### Running Tests
+```bash
+# Run pytest on all tests
+pytest
+
+# Run specific test file
+pytest tests/test_routines.py
+
+# Run with coverage
+pytest --cov=core --cov=api tests/
+```
+
+### Database Migrations
+For schema changes, create migration scripts in `config/` and reference them in `docker-compose.yml` or run manually:
+```bash
+psql -h localhost -U app -d app -f config/migration_name.sql
+```
+
+### Timezone Testing
+The system uses dual-path timezone support. Test both:
+1. **Request headers**: X-Timezone-Name (IANA) or X-Timezone-Offset
+2. **Stored preferences**: Verify `user_preferences.timezone_name` is persisted and read by scheduler
+
+### Discord Bot Development
+Bot commands are modular in `bot/commands/`. To add a command:
+1. Create a new command file in `bot/commands/`
+2. Import and register in `bot/bot.py`
+3. Bot automatically syncs commands to Discord on startup
+
+## Documentation
+
+Comprehensive documentation is available in `DOCUMENTATION.md`:
+- Detailed feature explanations
+- Database schema reference
+- Jury Council safety model (full spec)
+- Deployment & configuration
+- Contributing guidelines
+
 ## License
 
 MIT
+
+---
+
+**Built with evidence-based design for ADHD. Not a replacement for therapy or medication — a tool to support them.**

api/routes/medications.py

@@ -13,6 +13,7 @@ from psycopg2.extras import Json
 import core.auth as auth
 import core.postgres as postgres
 import core.tz as tz
+import core.adaptive_meds as adaptive_meds
 
 
 def _get_user_uuid(token):
@@ -145,56 +146,6 @@ def register(app):
         meds = postgres.select("medications", where={"user_uuid": user_uuid}, order_by="name")
         return flask.jsonify(meds), 200
 
-    def _time_str_to_minutes(time_str):
-        """Convert 'HH:MM' to minutes since midnight."""
-        parts = time_str.split(":")
-        return int(parts[0]) * 60 + int(parts[1])
-
-    def _get_routine_duration_minutes(routine_id):
-        """Get total duration of a routine from its steps."""
-        steps = postgres.select("routine_steps", where={"routine_id": routine_id})
-        total = sum(s.get("duration_minutes", 0) or 0 for s in steps)
-        return max(total, 1)
-
-    def _check_med_schedule_conflicts(user_uuid, new_times, new_days=None, exclude_med_id=None):
-        """Check if the proposed medication schedule conflicts with existing routines or medications.
-        Returns (has_conflict, conflict_message) tuple.
-        """
-        if not new_times:
-            return False, None
-
-        # Check conflicts with routines (duration-aware)
-        user_routines = postgres.select("routines", {"user_uuid": user_uuid})
-        for r in user_routines:
-            sched = postgres.select_one("routine_schedules", {"routine_id": r["id"]})
-            if not sched or not sched.get("time"):
-                continue
-            routine_days = sched.get("days", [])
-            if isinstance(routine_days, str):
-                routine_days = json.loads(routine_days)
-            if new_days and not any(d in routine_days for d in new_days):
-                continue
-            routine_start = _time_str_to_minutes(sched["time"])
-            routine_dur = _get_routine_duration_minutes(r["id"])
-            for t in new_times:
-                med_start = _time_str_to_minutes(t)
-                # Med falls within routine time range
-                if routine_start <= med_start < routine_start + routine_dur:
-                    return True, f"Time conflicts with routine: {r.get('name', 'Unnamed routine')}"
-
-        # Check conflicts with other medications
-        user_meds = postgres.select("medications", {"user_uuid": user_uuid, "active": True})
-        for med in user_meds:
-            if med["id"] == exclude_med_id:
-                continue
-            med_times = med.get("times", [])
-            if isinstance(med_times, str):
-                med_times = json.loads(med_times)
-            if any(t in med_times for t in new_times):
-                return True, f"Time conflicts with medication: {med.get('name', 'Unnamed medication')}"
-
-        return False, None
-
     @app.route("/api/medications", methods=["POST"])
     def api_addMedication():
         """Add a medication. Body: {name, dosage, unit, frequency, times?, days_of_week?, interval_days?, start_date?, notes?}"""
@@ -214,15 +165,6 @@ def register(app):
             if not data.get("start_date") or not data.get("interval_days"):
                 return flask.jsonify({"error": "every_n_days frequency requires both start_date and interval_days"}), 400
 
-        # Check for schedule conflicts
-        new_times = data.get("times", [])
-        new_days = data.get("days_of_week", [])
-        has_conflict, conflict_msg = _check_med_schedule_conflicts(
-            user_uuid, new_times, new_days
-        )
-        if has_conflict:
-            return flask.jsonify({"error": conflict_msg}), 409
-
         row = {
             "id": str(uuid.uuid4()),
             "user_uuid": user_uuid,
@@ -283,16 +225,6 @@ def register(app):
             "days_of_week", "interval_days", "start_date", "next_dose_date",
         ]
 
-        # Check for schedule conflicts if times are being updated
-        if "times" in data:
-            new_times = data.get("times", [])
-            new_days = data.get("days_of_week") or existing.get("days_of_week", [])
-            has_conflict, conflict_msg = _check_med_schedule_conflicts(
-                user_uuid, new_times, new_days, exclude_med_id=med_id
-            )
-            if has_conflict:
-                return flask.jsonify({"error": conflict_msg}), 409
-
         updates = {k: v for k, v in data.items() if k in allowed}
         if not updates:
             return flask.jsonify({"error": "no valid fields to update"}), 400
@@ -333,6 +265,11 @@ def register(app):
             "notes": data.get("notes"),
         }
         log = postgres.insert("med_logs", log_entry)
+        # Update adaptive schedule status so nags stop
+        try:
+            adaptive_meds.mark_med_taken(user_uuid, med_id, data.get("scheduled_time"))
+        except Exception:
+            pass  # Don't fail the take action if schedule update fails
         # Advance next_dose_date for interval meds
         if med.get("frequency") == "every_n_days" and med.get("interval_days"):
             next_date = _compute_next_dose_date(med)
@@ -359,6 +296,11 @@ def register(app):
             "notes": data.get("reason"),
         }
         log = postgres.insert("med_logs", log_entry)
+        # Update adaptive schedule status so nags stop
+        try:
+            adaptive_meds.mark_med_skipped(user_uuid, med_id, data.get("scheduled_time"))
+        except Exception:
+            pass  # Don't fail the skip action if schedule update fails
         # Advance next_dose_date for interval meds
         if med.get("frequency") == "every_n_days" and med.get("interval_days"):
             next_date = _compute_next_dose_date(med)

bot/bot.py

@@ -128,6 +128,7 @@ class JurySystem:
     async def retrieve(self, query_text, top_k=5):
         """Async retrieval — returns list of {metadata, score} dicts."""
         import asyncio
+
         return await asyncio.to_thread(self._retrieve_sync, query_text, top_k)
 
     async def query(self, query_text):
@@ -147,6 +148,7 @@ If the answer is not in the context, say you don't know based on the provided te
 Be concise, compassionate, and practical."""
 
             from ai.jury_council import generate_rag_answer
+
             return await generate_rag_answer(query_text, context_text, system_prompt)
         except Exception as e:
             return f"Error querying DBT knowledge base: {e}"
@@ -181,7 +183,9 @@ def apiRequest(method, endpoint, token=None, data=None, _retried=False):
         if resp.status_code == 401 and not _retried:
             new_token = _try_refresh_token_for_session(token)
             if new_token:
-                return apiRequest(method, endpoint, token=new_token, data=data, _retried=True)
+                return apiRequest(
+                    method, endpoint, token=new_token, data=data, _retried=True
+                )
         try:
             return resp.json(), resp.status_code
         except ValueError:
@@ -201,9 +205,12 @@ def _try_refresh_token_for_session(expired_token):
                 if cached:
                     refresh_token = cached.get("refresh_token")
             if refresh_token:
-                result, status = apiRequest("post", "/api/refresh",
+                result, status = apiRequest(
+                    "post",
+                    "/api/refresh",
                     data={"refresh_token": refresh_token},
-                                            _retried=True)
+                    _retried=True,
+                )
                 if status == 200 and "token" in result:
                     new_token = result["token"]
                     session["token"] = new_token
@@ -258,7 +265,8 @@ def negotiateToken(discord_id, username, password):
     # Try refresh token first (avoids sending password)
     if cached and cached.get("refresh_token"):
         result, status = apiRequest(
-            "post", "/api/refresh",
+            "post",
+            "/api/refresh",
             data={"refresh_token": cached["refresh_token"]},
             _retried=True,
         )
@@ -279,7 +287,9 @@ def negotiateToken(discord_id, username, password):
         and cached.get("hashed_password")
         and verifyPassword(password, cached.get("hashed_password"))
     ):
-        result, status = apiRequest("post", "/api/login", data=login_data, _retried=True)
+        result, status = apiRequest(
+            "post", "/api/login", data=login_data, _retried=True
+        )
         if status == 200 and "token" in result:
             token = result["token"]
             payload = decodeJwtPayload(token)
@@ -530,7 +540,9 @@ async def handleDBTQuery(message):
         if not jury_result.safe_questions:
             return True
 
-        await message.channel.send("🔍 Searching knowledge base with approved questions...")
+        await message.channel.send(
+            "🔍 Searching knowledge base with approved questions..."
+        )
 
         # Step 3: Multi-query retrieval — deduplicated by chunk ID
         seen_ids = set()
@@ -544,7 +556,9 @@ async def handleDBTQuery(message):
                     context_chunks.append(r["metadata"]["text"])
 
         if not context_chunks:
-            await message.channel.send("⚠️ No relevant content found in the knowledge base.")
+            await message.channel.send(
+                "⚠️ No relevant content found in the knowledge base."
+            )
             return True
 
         context = "\n\n---\n\n".join(context_chunks)
@@ -644,7 +658,8 @@ def _restore_sessions_from_cache():
         if not refresh_token:
             continue
         result, status = apiRequest(
-            "post", "/api/refresh",
+            "post",
+            "/api/refresh",
             data={"refresh_token": refresh_token},
             _retried=True,
         )
@@ -705,9 +720,14 @@ async def update_presence_tracking():
         import core.adaptive_meds as adaptive_meds
         import core.postgres as postgres
 
-        print(f"[DEBUG] Running presence tracking. Guilds: {len(client.guilds)}", flush=True)
+        print(
+            f"[DEBUG] Running presence tracking. Guilds: {len(client.guilds)}",
+            flush=True,
+        )
         for guild in client.guilds:
-            print(f"[DEBUG] Guild: {guild.name} ({guild.id}) - Members: {guild.member_count}")
+            print(
+                f"[DEBUG] Guild: {guild.name} ({guild.id}) - Members: {guild.member_count}"
+            )
 
         # Get all users with presence tracking enabled
         settings = postgres.select(
@@ -733,27 +753,46 @@ async def update_presence_tracking():
             # Get the member from a shared guild (needed for presence data)
             try:
                 member = None
+                try:
                     target_id = int(discord_user_id)
+                except (ValueError, TypeError):
+                    print(
+                        f"[DEBUG] Invalid Discord ID for user {user_uuid}: {discord_user_id}",
+                        flush=True,
+                    )
+                    continue
 
                 # Search through all guilds the bot is in
                 for guild in client.guilds:
                     member = guild.get_member(target_id)
-                    print(f"[DEBUG] Checked guild {guild.name}, member: {member}", flush=True)
+                    print(
+                        f"[DEBUG] Checked guild {guild.name}, member: {member}",
+                        flush=True,
+                    )
                     if member:
                         break
 
                 if not member:
-                    print(f"[DEBUG] User {discord_user_id} not found in any shared guild", flush=True)
+                    print(
+                        f"[DEBUG] User {discord_user_id} not found in any shared guild",
+                        flush=True,
+                    )
                     continue
 
                 # Check if user is online
                 is_online = member.status != discord.Status.offline
-                print(f"[DEBUG] User status: {member.status}, is_online: {is_online}", flush=True)
+                print(
+                    f"[DEBUG] User status: {member.status}, is_online: {is_online}",
+                    flush=True,
+                )
 
                 # Get current presence from DB
                 presence = adaptive_meds.get_user_presence(user_uuid)
                 was_online = presence.get("is_currently_online") if presence else False
-                print(f"[DEBUG] Previous state: {was_online}, Current: {is_online}", flush=True)
+                print(
+                    f"[DEBUG] Previous state: {was_online}, Current: {is_online}",
+                    flush=True,
+                )
 
                 # Update presence if changed
                 if is_online != was_online:
@@ -788,6 +827,7 @@ async def presenceTrackingLoop():
     except Exception as e:
         print(f"[ERROR] presenceTrackingLoop failed: {e}", flush=True)
         import traceback
+
         traceback.print_exc()
 
 

bot/commands/routines.py

@@ -217,12 +217,13 @@ async def handle_routine(message, session, parsed):
             await message.channel.send("When should this routine be scheduled? (e.g., 'Monday Wednesday Friday at 7am')")
             return
 
-        # Build schedule data
+        # Build schedule data (API expects "days" and "time")
         schedule_data = {}
         if days_of_week:
-            schedule_data["days_of_week"] = days_of_week
+            schedule_data["days"] = days_of_week
         if times:
-            schedule_data["times"] = times
+            schedule_data["time"] = times[0]
+            schedule_data["remind"] = True
 
         resp, status = api_request("put", f"/api/routines/{routine_id}/schedule", token, schedule_data)
         if status == 200:

core/adaptive_meds.py

@@ -10,10 +10,10 @@ This module handles:
 
 import json
 import uuid
-from datetime import datetime, timedelta, time
+from datetime import datetime, timedelta, time, timezone
 from typing import Optional, Dict, List, Tuple
 import core.postgres as postgres
-from core.tz import user_now, user_today_for
+from core.tz import user_now, user_now_for, user_today_for, tz_for_user
 
 
 def _normalize_time(val):
@@ -42,12 +42,24 @@ def get_user_presence(user_uuid: str) -> Optional[Dict]:
 
 
 def update_user_presence(user_uuid: str, discord_user_id: str, is_online: bool):
-    """Update user's presence status."""
+    """Update user's presence status. If a wake event is detected (came online
+    after 30+ minutes offline), recalculates today's adaptive medication schedules."""
     now = datetime.utcnow()
 
     presence = get_user_presence(user_uuid)
+    is_wake_event = False
 
     if presence:
+        # Detect wake event before updating
+        if is_online and not presence.get("is_currently_online"):
+            last_offline = presence.get("last_offline_at")
+            if last_offline:
+                if isinstance(last_offline, datetime) and last_offline.tzinfo is None:
+                    last_offline = last_offline.replace(tzinfo=timezone.utc)
+                offline_duration = (now.replace(tzinfo=timezone.utc) - last_offline).total_seconds()
+                if offline_duration > 1800:  # 30 minutes
+                    is_wake_event = True
+
         # Update existing record
         updates = {"is_currently_online": is_online, "updated_at": now}
 
@@ -71,6 +83,26 @@ def update_user_presence(user_uuid: str, discord_user_id: str, is_online: bool):
         }
         postgres.insert("user_presence", data)
 
+    # On wake event, recalculate today's adaptive schedules
+    if is_wake_event:
+        _recalculate_schedules_on_wake(user_uuid, now)
+
+
+def _recalculate_schedules_on_wake(user_uuid: str, wake_time: datetime):
+    """Recalculate today's pending adaptive schedules using the actual wake time."""
+    settings = get_adaptive_settings(user_uuid)
+    if not settings or not settings.get("adaptive_timing_enabled"):
+        return
+
+    try:
+        meds = postgres.select("medications", {"user_uuid": user_uuid, "active": True})
+        for med in meds:
+            times = med.get("times", [])
+            if times:
+                create_daily_schedule(user_uuid, med["id"], times, recalculate=True)
+    except Exception:
+        pass  # Best-effort — don't break presence tracking if this fails
+
 
 def record_presence_event(user_uuid: str, event_type: str, timestamp: datetime):
     """Record a presence event in the history."""
@@ -182,12 +214,8 @@ def calculate_adjusted_times(
         # Return base times with 0 offset
         return [(t, 0) for t in base_times]
 
-    # Get user's timezone
+    # Get current time in user's timezone (works in both request and scheduler context)
-    prefs = postgres.select("user_preferences", {"user_uuid": user_uuid})
+    user_current_time = user_now_for(user_uuid)
-    offset_minutes = prefs[0].get("timezone_offset", 0) if prefs else 0
-
-    # Get current time in user's timezone
-    user_current_time = user_now(offset_minutes)
     today = user_current_time.date()
 
     # Determine wake time
@@ -270,7 +298,7 @@ def should_send_nag(
             return False, "User offline"
 
     # Get today's schedule record for this specific time slot
-    today = current_time.date()
+    today = user_today_for(user_uuid)
     query = {"user_uuid": user_uuid, "medication_id": med_id, "adjustment_date": today}
     if scheduled_time is not None:
         query["adjusted_time"] = scheduled_time
@@ -291,30 +319,89 @@ def should_send_nag(
     nag_interval = settings.get("nag_interval_minutes", 15)
 
     if last_nag:
+        if isinstance(last_nag, datetime) and last_nag.tzinfo is None:
+            last_nag = last_nag.replace(tzinfo=timezone.utc)
         time_since_last_nag = (current_time - last_nag).total_seconds() / 60
         if time_since_last_nag < nag_interval:
             return False, f"Too soon ({int(time_since_last_nag)} < {nag_interval} min)"
+    else:
+        # First nag: require at least nag_interval minutes since the scheduled dose time
+        if scheduled_time:
+            sched_hour, sched_min = int(scheduled_time[:2]), int(scheduled_time[3:5])
+            sched_dt = current_time.replace(hour=sched_hour, minute=sched_min, second=0, microsecond=0)
+            minutes_since_dose = (current_time - sched_dt).total_seconds() / 60
+            if minutes_since_dose < nag_interval:
+                return False, f"Too soon after dose time ({int(minutes_since_dose)} < {nag_interval} min)"
 
-    # Check if this specific dose was already taken today
+    # Check if this specific dose was already taken or skipped today
     logs = postgres.select(
         "med_logs",
         {
             "medication_id": med_id,
             "user_uuid": user_uuid,
-            "action": "taken",
-            "scheduled_time": scheduled_time,
         },
     )
 
-    # Filter to today's logs for this time slot
+    # Get medication times to calculate dose interval for proximity check
-    today_logs = [
+    med = postgres.select_one("medications", {"id": med_id})
-        log
+    dose_interval_minutes = 60  # default fallback
-        for log in logs
+    if med and med.get("times"):
-        if log.get("created_at") and log["created_at"].date() == today
+        times = med["times"]
-    ]
+        if len(times) >= 2:
+            time_minutes = []
+            for t in times:
+                t = _normalize_time(t)
+                if t:
+                    h, m = int(t[:2]), int(t[3:5])
+                    time_minutes.append(h * 60 + m)
+            time_minutes.sort()
+            intervals = []
+            for i in range(1, len(time_minutes)):
+                intervals.append(time_minutes[i] - time_minutes[i - 1])
+            if intervals:
+                dose_interval_minutes = min(intervals)
 
-    if today_logs:
+    proximity_window = max(30, dose_interval_minutes // 2)
-        return False, "Already taken today"
+
+    # Filter to today's logs and check for this specific dose
+    user_tz = tz_for_user(user_uuid)
+    for log in logs:
+        action = log.get("action")
+        if action not in ("taken", "skipped"):
+            continue
+
+        created_at = log.get("created_at")
+        if not created_at:
+            continue
+
+        # created_at is stored as UTC but timezone-naive; convert to user's timezone
+        if created_at.tzinfo is None:
+            created_at = created_at.replace(tzinfo=timezone.utc)
+        created_at_local = created_at.astimezone(user_tz)
+
+        if created_at_local.date() != today:
+            continue
+
+        log_scheduled_time = log.get("scheduled_time")
+        if log_scheduled_time:
+            log_scheduled_time = _normalize_time(log_scheduled_time)
+            if log_scheduled_time == scheduled_time:
+                return False, f"Already {action} today"
+        else:
+            if scheduled_time:
+                log_hour = created_at_local.hour
+                log_min = created_at_local.minute
+                sched_hour, sched_min = (
+                    int(scheduled_time[:2]),
+                    int(scheduled_time[3:5]),
+                )
+                log_mins = log_hour * 60 + log_min
+                sched_mins = sched_hour * 60 + sched_min
+                diff_minutes = abs(log_mins - sched_mins)
+                # Handle midnight wraparound (e.g. 23:00 vs 00:42)
+                diff_minutes = min(diff_minutes, 1440 - diff_minutes)
+                if diff_minutes <= proximity_window:
+                    return False, f"Already {action} today"
 
     return True, "Time to nag"
 
@@ -335,13 +422,18 @@ def record_nag_sent(user_uuid: str, med_id: str, scheduled_time):
 
         postgres.update(
             "medication_schedules",
-            {"nag_count": new_nag_count, "last_nag_at": datetime.utcnow()},
+            {"nag_count": new_nag_count, "last_nag_at": datetime.now(timezone.utc)},
             {"id": schedule["id"]},
         )
 
 
-def create_daily_schedule(user_uuid: str, med_id: str, base_times: List[str]):
+def create_daily_schedule(user_uuid: str, med_id: str, base_times: List[str], recalculate: bool = False):
-    """Create today's medication schedule with adaptive adjustments."""
+    """Create today's medication schedule with adaptive adjustments.
+
+    If recalculate=True, deletes existing *pending* schedules and recreates them
+    with updated adaptive timing (e.g. after a wake event is detected).
+    Already-taken or skipped schedules are preserved.
+    """
     today = user_today_for(user_uuid)
 
     # Check if schedule already exists
@@ -350,14 +442,62 @@ def create_daily_schedule(user_uuid: str, med_id: str, base_times: List[str]):
         {"user_uuid": user_uuid, "medication_id": med_id, "adjustment_date": today},
     )
 
-    if existing:
+    if existing and not recalculate:
+        return
+
+    if existing and recalculate:
+        # Only delete pending schedules — preserve taken/skipped
+        for sched in existing:
+            if sched.get("status") == "pending":
+                postgres.delete("medication_schedules", {"id": sched["id"]})
+        # Check if any pending remain to create
+        remaining = [s for s in existing if s.get("status") != "pending"]
+        completed_base_times = set()
+        for s in remaining:
+            bt = _normalize_time(s.get("base_time"))
+            if bt:
+                completed_base_times.add(bt)
+        # Only create schedules for times that haven't been taken/skipped
+        base_times = [t for t in base_times if t not in completed_base_times]
+        if not base_times:
             return
 
     # Calculate adjusted times
     adjusted_times = calculate_adjusted_times(user_uuid, base_times)
 
+    # Check recent med logs to skip doses already taken/skipped.
+    # Handles cross-midnight: if adaptive offset shifts 23:00 → 00:42 today,
+    # but the user already took the 23:00 dose last night, don't schedule it.
+    # Yesterday's logs only suppress if the scheduled_time is late-night
+    # (21:00+), since only those could plausibly cross midnight with an offset.
+    user_tz = tz_for_user(user_uuid)
+    yesterday = today - timedelta(days=1)
+    recent_logs = postgres.select("med_logs", {"medication_id": med_id, "user_uuid": user_uuid})
+    taken_base_times = set()
+    for log in recent_logs:
+        if log.get("action") not in ("taken", "skipped"):
+            continue
+        created_at = log.get("created_at")
+        if not created_at:
+            continue
+        if created_at.tzinfo is None:
+            created_at = created_at.replace(tzinfo=timezone.utc)
+        log_date = created_at.astimezone(user_tz).date()
+        if log_date == today:
+            log_sched = _normalize_time(log.get("scheduled_time"))
+            if log_sched:
+                taken_base_times.add(log_sched)
+        elif log_date == yesterday:
+            # Only suppress cross-midnight doses (late-night times like 21:00+)
+            log_sched = _normalize_time(log.get("scheduled_time"))
+            if log_sched and log_sched >= "21:00":
+                taken_base_times.add(log_sched)
+
     # Create schedule records for each time
     for base_time, (adjusted_time, offset) in zip(base_times, adjusted_times):
+        if base_time in taken_base_times:
+            continue
+
         data = {
             "id": str(uuid.uuid4()),
             "user_uuid": user_uuid,
@@ -373,17 +513,40 @@ def create_daily_schedule(user_uuid: str, med_id: str, base_times: List[str]):
 
 
 def mark_med_taken(user_uuid: str, med_id: str, scheduled_time):
-    """Mark a medication as taken."""
+    """Mark a medication schedule as taken."""
+    _mark_med_status(user_uuid, med_id, scheduled_time, "taken")
+
+
+def mark_med_skipped(user_uuid: str, med_id: str, scheduled_time):
+    """Mark a medication schedule as skipped."""
+    _mark_med_status(user_uuid, med_id, scheduled_time, "skipped")
+
+
+def _mark_med_status(user_uuid: str, med_id: str, scheduled_time, status: str):
+    """Update a medication schedule's status for today."""
     scheduled_time = _normalize_time(scheduled_time)
     today = user_today_for(user_uuid)
 
-    postgres.update(
+    # Try matching by adjusted_time first
-        "medication_schedules",
+    where = {
-        {"status": "taken"},
-        {
         "user_uuid": user_uuid,
         "medication_id": med_id,
         "adjustment_date": today,
-            "adjusted_time": scheduled_time,
+    }
-        },
+    if scheduled_time is not None:
-    )
+        where["adjusted_time"] = scheduled_time
+
+    schedules = postgres.select("medication_schedules", where)
+    if schedules:
+        postgres.update("medication_schedules", {"status": status}, {"id": schedules[0]["id"]})
+    elif scheduled_time is not None:
+        # Fallback: try matching by base_time (in case adjusted == base)
+        where_base = {
+            "user_uuid": user_uuid,
+            "medication_id": med_id,
+            "adjustment_date": today,
+            "base_time": scheduled_time,
+        }
+        schedules_base = postgres.select("medication_schedules", where_base)
+        if schedules_base:
+            postgres.update("medication_schedules", {"status": status}, {"id": schedules_base[0]["id"]})

regenerate_embeddings.py

@@ -0,0 +1,56 @@
+#!/usr/bin/env python3
+"""Regenerate DBT embeddings with qwen/qwen3-embedding-8b model (384 dimensions)"""
+
+import json
+import os
+from openai import OpenAI
+import time
+
+# Load config
+with open("config.json", "r") as f:
+    config = json.load(f)
+
+# Initialize OpenAI client with OpenRouter
+client = OpenAI(
+    base_url="https://openrouter.ai/api/v1",
+    api_key=config["openrouter_api_key"],
+)
+
+# Load text data
+with open("bot/data/dbt_knowledge.text.json", "r") as f:
+    text_data = json.load(f)
+
+print(f"Regenerating embeddings for {len(text_data)} chunks...")
+
+# Generate embeddings
+embeddings_data = []
+for i, item in enumerate(text_data):
+    try:
+        response = client.embeddings.create(
+            model="qwen/qwen3-embedding-8b",
+            input=item["text"]
+        )
+        embedding = response.data[0].embedding
+        
+        embeddings_data.append({
+            "id": item["id"],
+            "source": item["source"],
+            "text": item["text"],
+            "embedding": embedding
+        })
+        
+        if (i + 1) % 10 == 0:
+            print(f"Processed {i + 1}/{len(text_data)} chunks...")
+            
+        # Small delay to avoid rate limits
+        time.sleep(0.1)
+        
+    except Exception as e:
+        print(f"Error processing item {i}: {e}")
+        continue
+
+# Save new embeddings
+with open("bot/data/dbt_knowledge.embeddings.json", "w") as f:
+    json.dump(embeddings_data, f)
+
+print(f"\nDone! Generated {len(embeddings_data)} embeddings with {len(embeddings_data[0]['embedding'])} dimensions")

scheduler/daemon.py

@@ -26,6 +26,17 @@ def _user_now_for(user_uuid):
     return tz.user_now_for(user_uuid)
 
 
+def _utc_to_local_date(created_at, user_tz):
+    """Convert a DB created_at (naive UTC datetime) to a local date string YYYY-MM-DD."""
+    if created_at is None:
+        return ""
+    if isinstance(created_at, datetime):
+        if created_at.tzinfo is None:
+            created_at = created_at.replace(tzinfo=timezone.utc)
+        return created_at.astimezone(user_tz).date().isoformat()
+    return str(created_at)[:10]
+
+
 def check_medication_reminders():
     """Check for medications due now and send notifications."""
     try:
@@ -47,6 +58,7 @@ def check_medication_reminders():
             current_day = now.strftime("%a").lower()
             today = now.date()
             today_str = today.isoformat()
+            user_tz = tz.tz_for_user(user_uuid)
 
             for med in user_med_list:
                 freq = med.get("frequency", "daily")
@@ -83,13 +95,13 @@ def check_medication_reminders():
                 if current_time not in times:
                     continue
 
-                # Already taken today? Check by created_at date
+                # Already taken today? Check by created_at date in user's timezone
                 logs = postgres.select(
                     "med_logs", where={"medication_id": med["id"], "action": "taken"}
                 )
                 already_taken = any(
                     log.get("scheduled_time") == current_time
-                    and str(log.get("created_at", ""))[:10] == today_str
+                    and _utc_to_local_date(log.get("created_at"), user_tz) == today_str
                     for log in logs
                 )
                 if already_taken:
@@ -111,20 +123,25 @@ def check_routine_reminders():
         from datetime import date as date_type
 
         schedules = postgres.select("routine_schedules", where={"remind": True})
+        logger.info(f"Routine reminders: found {len(schedules)} schedule(s) with remind=True")
 
         for schedule in schedules:
             routine = postgres.select_one("routines", {"id": schedule["routine_id"]})
             if not routine:
+                logger.warning(f"Routine not found for schedule {schedule['id']}")
                 continue
 
             now = _user_now_for(routine["user_uuid"])
             current_time = now.strftime("%H:%M")
             today = now.date()
 
-            if current_time != schedule.get("time"):
+            sched_time = schedule.get("time")
+            if current_time != sched_time:
                 continue
 
-            frequency = schedule.get("frequency", "weekly")
+            logger.info(f"Routine '{routine['name']}' time match at {current_time}")
+
+            frequency = schedule.get("frequency") or "weekly"
             if frequency == "every_n_days":
                 start = schedule.get("start_date")
                 interval = schedule.get("interval_days")
@@ -134,14 +151,19 @@ def check_routine_reminders():
                         if isinstance(start, date_type)
                         else datetime.strptime(str(start), "%Y-%m-%d").date()
                     )
-                    if (today - start_d).days < 0 or (today - start_d).days % interval != 0:
+                    if (today - start_d).days < 0 or (
+                        today - start_d
+                    ).days % interval != 0:
+                        logger.info(f"Routine '{routine['name']}' skipped: not due today (every {interval} days from {start_d})")
                         continue
                 else:
+                    logger.warning(f"Routine '{routine['name']}' skipped: every_n_days but missing start_date={start} or interval_days={interval}")
                     continue
             else:
                 current_day = now.strftime("%a").lower()
                 days = schedule.get("days", [])
                 if current_day not in days:
+                    logger.info(f"Routine '{routine['name']}' skipped: {current_day} not in {days}")
                     continue
 
             user_settings = notifications.getNotificationSettings(routine["user_uuid"])
@@ -150,8 +172,11 @@ def check_routine_reminders():
                 notifications._sendToEnabledChannels(
                     user_settings, msg, user_uuid=routine["user_uuid"]
                 )
+                logger.info(f"Routine reminder sent for '{routine['name']}'")
+            else:
+                logger.warning(f"No notification settings for user {routine['user_uuid']}, skipping routine '{routine['name']}'")
     except Exception as e:
-        logger.error(f"Error checking routine reminders: {e}")
+        logger.error(f"Error checking routine reminders: {e}", exc_info=True)
 
 
 def check_refills():
@@ -213,6 +238,7 @@ def check_adaptive_medication_reminders():
             now = _user_now_for(user_uuid)
             current_time = now.strftime("%H:%M")
             today = now.date()
+            user_tz = tz.tz_for_user(user_uuid)
 
             # Check if adaptive timing is enabled
             settings = adaptive_meds.get_adaptive_settings(user_uuid)
@@ -248,18 +274,37 @@ def check_adaptive_medication_reminders():
                     else:
                         continue
 
-                # Get today's schedule
+                # Get today's schedule (any status — we filter below)
                 schedules = postgres.select(
                     "medication_schedules",
                     where={
                         "user_uuid": user_uuid,
                         "medication_id": med["id"],
                         "adjustment_date": today,
-                        "status": "pending",
                     },
                 )
 
+                # If no schedules exist yet, create them on demand
+                if not schedules:
+                    times = med.get("times", [])
+                    if times:
+                        try:
+                            adaptive_meds.create_daily_schedule(user_uuid, med["id"], times)
+                            schedules = postgres.select(
+                                "medication_schedules",
+                                where={
+                                    "user_uuid": user_uuid,
+                                    "medication_id": med["id"],
+                                    "adjustment_date": today,
+                                },
+                            )
+                        except Exception as e:
+                            logger.warning(f"Could not create on-demand schedule for {med['id']}: {e}")
+
                 for sched in schedules:
+                    # Skip already-taken or skipped schedules
+                    if sched.get("status") in ("taken", "skipped"):
+                        continue
                     # Check if it's time to take this med
                     if adaptive_enabled:
                         # Use adjusted time
@@ -277,32 +322,40 @@ def check_adaptive_medication_reminders():
                     if check_time != current_time:
                         continue
 
-                    # Check if already taken
+                    # Check if already taken or skipped for this time slot today
                     logs = postgres.select(
                         "med_logs",
                         where={
                             "medication_id": med["id"],
                             "user_uuid": user_uuid,
-                            "action": "taken",
                         },
                     )
 
-                    already_taken = any(
+                    already_handled = any(
-                        str(log.get("created_at", ""))[:10] == today.isoformat()
+                        log.get("action") in ("taken", "skipped")
+                        and log.get("scheduled_time") == check_time
+                        and _utc_to_local_date(log.get("created_at"), user_tz)
+                        == today.isoformat()
                         for log in logs
                     )
 
-                    if already_taken:
+                    if already_handled:
                         continue
 
-                    # Send notification
+                    # Send notification — display base_time to the user
+                    base_display = sched.get("base_time")
+                    if isinstance(base_display, time_type):
+                        base_display = base_display.strftime("%H:%M")
+                    elif base_display is not None:
+                        base_display = str(base_display)[:5]
+
                     user_settings = notifications.getNotificationSettings(user_uuid)
                     if user_settings:
                         offset = sched.get("adjustment_minutes", 0)
                         if offset > 0:
-                            msg = f"⏰ Time to take {med['name']} ({med['dosage']} {med['unit']}) · {check_time} (adjusted +{offset}min)"
+                            msg = f"⏰ Time to take {med['name']} ({med['dosage']} {med['unit']}) · {base_display} (adjusted +{offset}min)"
                         else:
-                            msg = f"⏰ Time to take {med['name']} ({med['dosage']} {med['unit']}) · {check_time}"
+                            msg = f"⏰ Time to take {med['name']} ({med['dosage']} {med['unit']}) · {base_display}"
 
                         notifications._sendToEnabledChannels(
                             user_settings, msg, user_uuid=user_uuid
@@ -352,7 +405,9 @@ def check_nagging():
                     },
                 )
             except Exception as e:
-                logger.warning(f"Could not query medication_schedules for {med_id}: {e}")
+                logger.warning(
+                    f"Could not query medication_schedules for {med_id}: {e}"
+                )
                 # Table may not exist yet
                 continue
 
@@ -360,7 +415,9 @@ def check_nagging():
             if not schedules:
                 if not _is_med_due_today(med, today):
                     continue
-                logger.info(f"No schedules found for medication {med_id}, attempting to create")
+                logger.info(
+                    f"No schedules found for medication {med_id}, attempting to create"
+                )
                 times = med.get("times", [])
                 if times:
                     try:
@@ -392,11 +449,8 @@ def check_nagging():
                 if not should_nag:
                     continue
 
-                # Get the time to display
+                # Always display the base_time (the user's actual dose time),
-                adaptive_enabled = settings.get("adaptive_timing_enabled")
+                # not the internal adjusted_time used for scheduling.
-                if adaptive_enabled:
-                    display_time = sched.get("adjusted_time")
-                else:
                 display_time = sched.get("base_time")
                 # Normalize TIME objects for display
                 if isinstance(display_time, time_type):
@@ -531,9 +585,7 @@ def _check_per_user_midnight_schedules():
                         continue
                     times = med.get("times", [])
                     if times:
-                        adaptive_meds.create_daily_schedule(
+                        adaptive_meds.create_daily_schedule(user_uuid, med["id"], times)
-                            user_uuid, med["id"], times
-                        )
         except Exception as e:
             logger.warning(
                 f"Could not create adaptive schedules for user {user_uuid}: {e}"
@@ -543,6 +595,7 @@ def _check_per_user_midnight_schedules():
 def check_task_reminders():
     """Check one-off tasks for advance and at-time reminders."""
     from datetime import timedelta
+
     try:
         tasks = postgres.select("tasks", where={"status": "pending"})
         if not tasks:
@@ -575,15 +628,24 @@ def check_task_reminders():
                 # Advance reminder
                 if reminder_min > 0 and not task.get("advance_notified"):
                     adv_dt = sched_dt - timedelta(minutes=reminder_min)
-                    if adv_dt.date() == current_date and adv_dt.strftime("%H:%M") == current_hhmm:
+                    if (
+                        adv_dt.date() == current_date
+                        and adv_dt.strftime("%H:%M") == current_hhmm
+                    ):
                         if user_settings is None:
-                            user_settings = notifications.getNotificationSettings(user_uuid)
+                            user_settings = notifications.getNotificationSettings(
+                                user_uuid
+                            )
                         if user_settings:
                             msg = f"⏰ In {reminder_min} min: {task['title']}"
                             if task.get("description"):
                                 msg += f" — {task['description']}"
-                            notifications._sendToEnabledChannels(user_settings, msg, user_uuid=user_uuid)
+                            notifications._sendToEnabledChannels(
-                        postgres.update("tasks", {"advance_notified": True}, {"id": task["id"]})
+                                user_settings, msg, user_uuid=user_uuid
+                            )
+                        postgres.update(
+                            "tasks", {"advance_notified": True}, {"id": task["id"]}
+                        )
 
                 # At-time reminder
                 if sched_date == current_date and sched_hhmm == current_hhmm:
@@ -593,10 +655,15 @@ def check_task_reminders():
                         msg = f"📋 Now: {task['title']}"
                         if task.get("description"):
                             msg += f"\n{task['description']}"
-                        notifications._sendToEnabledChannels(user_settings, msg, user_uuid=user_uuid)
+                        notifications._sendToEnabledChannels(
+                            user_settings, msg, user_uuid=user_uuid
+                        )
                     postgres.update(
                         "tasks",
-                        {"status": "notified", "updated_at": datetime.utcnow().isoformat()},
+                        {
+                            "status": "notified",
+                            "updated_at": datetime.utcnow().isoformat(),
+                        },
                         {"id": task["id"]},
                     )
     except Exception as e:
@@ -608,13 +675,14 @@ def poll_callback():
     # Create daily schedules per-user at their local midnight
     _check_per_user_midnight_schedules()
 
-    # Check reminders - use both original and adaptive checks
+    # Check medication reminders (adaptive path handles both adaptive and non-adaptive)
     logger.info("Checking medication reminders")
-    check_medication_reminders()
     try:
         check_adaptive_medication_reminders()
     except Exception as e:
         logger.warning(f"Adaptive medication reminder check failed: {e}")
+        # Fall back to basic reminders if adaptive check fails entirely
+        check_medication_reminders()
 
     # Check for nags - log as error to help with debugging
     try:

synculous-client/src/app/dashboard/medications/new/page.tsx

@@ -3,7 +3,7 @@
 import { useState } from 'react';
 import { useRouter } from 'next/navigation';
 import api from '@/lib/api';
-import { ArrowLeftIcon } from '@/components/ui/Icons';
+import { ArrowLeftIcon, PlusIcon, TrashIcon } from '@/components/ui/Icons';
 
 const DAY_OPTIONS = [
   { value: 'mon', label: 'Mon' },
@@ -15,96 +15,78 @@ const DAY_OPTIONS = [
   { value: 'sun', label: 'Sun' },
 ];
 
-export default function NewMedicationPage() {
+interface MedEntry {
-  const router = useRouter();
+  id: string;
-  const [name, setName] = useState('');
+  name: string;
-  const [dosage, setDosage] = useState('');
+  dosage: string;
-  const [unit, setUnit] = useState('mg');
+  unit: string;
-  const [frequency, setFrequency] = useState('daily');
+  frequency: string;
-  const [times, setTimes] = useState<string[]>(['08:00']);
+  times: string[];
-  const [daysOfWeek, setDaysOfWeek] = useState<string[]>([]);
+  daysOfWeek: string[];
-  const [intervalDays, setIntervalDays] = useState(7);
+  intervalDays: number;
-  const [startDate, setStartDate] = useState(new Date().toISOString().slice(0, 10));
+  startDate: string;
-  const [isLoading, setIsLoading] = useState(false);
-  const [error, setError] = useState('');
-
-  const handleAddTime = () => {
-    setTimes([...times, '12:00']);
-  };
-
-  const handleRemoveTime = (index: number) => {
-    setTimes(times.filter((_, i) => i !== index));
-  };
-
-  const handleTimeChange = (index: number, value: string) => {
-    const newTimes = [...times];
-    newTimes[index] = value;
-    setTimes(newTimes);
-  };
-
-  const toggleDay = (day: string) => {
-    setDaysOfWeek(prev =>
-      prev.includes(day) ? prev.filter(d => d !== day) : [...prev, day]
-    );
-  };
-
-  const handleSubmit = async (e: React.FormEvent) => {
-    e.preventDefault();
-    if (!name.trim() || !dosage.trim()) {
-      setError('Name and dosage are required');
-      return;
-    }
-    if (frequency === 'specific_days' && daysOfWeek.length === 0) {
-      setError('Select at least one day of the week');
-      return;
 }
 
-    setIsLoading(true);
+function blankEntry(): MedEntry {
-    setError('');
+  return {
+    id: `med-${Date.now()}-${Math.random()}`,
+    name: '',
+    dosage: '',
+    unit: 'mg',
+    frequency: 'daily',
+    times: ['08:00'],
+    daysOfWeek: [],
+    intervalDays: 7,
+    startDate: new Date().toISOString().slice(0, 10),
+  };
+}
 
-    try {
+function MedCard({
-      await api.medications.create({
+  entry,
-        name,
+  index,
-        dosage,
+  total,
-        unit,
+  onChange,
-        frequency,
+  onRemove,
-        times: frequency === 'as_needed' ? [] : times,
+}: {
-        ...(frequency === 'specific_days' && { days_of_week: daysOfWeek }),
+  entry: MedEntry;
-        ...(frequency === 'every_n_days' && { interval_days: intervalDays, start_date: startDate }),
+  index: number;
+  total: number;
+  onChange: (updates: Partial<MedEntry>) => void;
+  onRemove: () => void;
+}) {
+  const handleAddTime = () => onChange({ times: [...entry.times, '12:00'] });
+  const handleRemoveTime = (i: number) => onChange({ times: entry.times.filter((_, idx) => idx !== i) });
+  const handleTimeChange = (i: number, val: string) => {
+    const t = [...entry.times];
+    t[i] = val;
+    onChange({ times: t });
+  };
+  const toggleDay = (day: string) =>
+    onChange({
+      daysOfWeek: entry.daysOfWeek.includes(day)
+        ? entry.daysOfWeek.filter(d => d !== day)
+        : [...entry.daysOfWeek, day],
     });
-      router.push('/dashboard/medications');
-    } catch (err) {
-      setError((err as Error).message || 'Failed to add medication');
-    } finally {
-      setIsLoading(false);
-    }
-  };
 
   return (
-    <div className="min-h-screen bg-gray-50 dark:bg-gray-950">
-      <header className="bg-white dark:bg-gray-900 border-b border-gray-200 dark:border-gray-700 sticky top-0 z-10">
-        <div className="flex items-center gap-3 px-4 py-3">
-          <button onClick={() => router.back()} className="p-1 text-gray-600 dark:text-gray-400">
-            <ArrowLeftIcon size={24} />
-          </button>
-          <h1 className="text-xl font-bold text-gray-900 dark:text-gray-100">Add Medication</h1>
-        </div>
-      </header>
-
-      <form onSubmit={handleSubmit} className="p-4 space-y-6">
-        {error && (
-          <div className="bg-red-50 dark:bg-red-900/30 text-red-600 dark:text-red-400 px-4 py-3 rounded-lg text-sm">
-            {error}
-          </div>
-        )}
-
     <div className="bg-white dark:bg-gray-800 rounded-xl p-4 shadow-sm space-y-4">
+      <div className="flex items-center justify-between">
+        <span className="text-sm font-semibold text-gray-500 dark:text-gray-400">
+          Medication {index + 1}
+        </span>
+        {total > 1 && (
+          <button type="button" onClick={onRemove} className="text-red-500 dark:text-red-400 p-1">
+            <TrashIcon size={18} />
+          </button>
+        )}
+      </div>
+
       <div>
-            <label className="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-1">Medication Name</label>
+        <label className="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-1">Name</label>
         <input
           type="text"
-              value={name}
+          value={entry.name}
-              onChange={(e) => setName(e.target.value)}
+          onChange={e => onChange({ name: e.target.value })}
           placeholder="e.g., Vitamin D"
           className="w-full px-4 py-3 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-700 text-gray-900 dark:text-gray-100 placeholder-gray-400 dark:placeholder-gray-500 focus:ring-2 focus:ring-indigo-500 outline-none"
         />
@@ -115,8 +97,8 @@ export default function NewMedicationPage() {
           <label className="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-1">Dosage</label>
           <input
             type="text"
-                value={dosage}
+            value={entry.dosage}
-                onChange={(e) => setDosage(e.target.value)}
+            onChange={e => onChange({ dosage: e.target.value })}
             placeholder="e.g., 1000"
             className="w-full px-4 py-3 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-700 text-gray-900 dark:text-gray-100 placeholder-gray-400 dark:placeholder-gray-500 focus:ring-2 focus:ring-indigo-500 outline-none"
           />
@@ -124,8 +106,8 @@ export default function NewMedicationPage() {
         <div>
           <label className="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-1">Unit</label>
           <select
-                value={unit}
+            value={entry.unit}
-                onChange={(e) => setUnit(e.target.value)}
+            onChange={e => onChange({ unit: e.target.value })}
             className="w-full px-4 py-3 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-700 text-gray-900 dark:text-gray-100 focus:ring-2 focus:ring-indigo-500 outline-none"
           >
             <option value="mg">mg</option>
@@ -142,8 +124,8 @@ export default function NewMedicationPage() {
       <div>
         <label className="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-1">Frequency</label>
         <select
-              value={frequency}
+          value={entry.frequency}
-              onChange={(e) => setFrequency(e.target.value)}
+          onChange={e => onChange({ frequency: e.target.value })}
           className="w-full px-4 py-3 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-700 text-gray-900 dark:text-gray-100 focus:ring-2 focus:ring-indigo-500 outline-none"
         >
           <option value="daily">Daily</option>
@@ -153,8 +135,7 @@ export default function NewMedicationPage() {
         </select>
       </div>
 
-          {/* Day-of-week picker for specific_days */}
+      {entry.frequency === 'specific_days' && (
-          {frequency === 'specific_days' && (
         <div>
           <label className="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-2">Days</label>
           <div className="flex gap-2 flex-wrap">
@@ -164,7 +145,7 @@ export default function NewMedicationPage() {
                 type="button"
                 onClick={() => toggleDay(value)}
                 className={`px-3 py-2 rounded-lg text-sm font-medium border transition-colors ${
-                      daysOfWeek.includes(value)
+                  entry.daysOfWeek.includes(value)
                     ? 'bg-indigo-600 text-white border-indigo-600'
                     : 'bg-white dark:bg-gray-700 text-gray-700 dark:text-gray-300 border-gray-300 dark:border-gray-600'
                 }`}
@@ -176,33 +157,31 @@ export default function NewMedicationPage() {
         </div>
       )}
 
-          {/* Interval settings for every_n_days */}
+      {entry.frequency === 'every_n_days' && (
-          {frequency === 'every_n_days' && (
         <div className="space-y-4">
           <div>
             <label className="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-1">Every N Days</label>
             <input
               type="number"
               min={1}
-                  value={intervalDays}
+              value={entry.intervalDays}
-                  onChange={(e) => setIntervalDays(parseInt(e.target.value) || 1)}
+              onChange={e => onChange({ intervalDays: parseInt(e.target.value) || 1 })}
-                  className="w-full px-4 py-3 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-700 text-gray-900 dark:text-gray-100 placeholder-gray-400 dark:placeholder-gray-500 focus:ring-2 focus:ring-indigo-500 outline-none"
+              className="w-full px-4 py-3 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-700 text-gray-900 dark:text-gray-100 focus:ring-2 focus:ring-indigo-500 outline-none"
             />
           </div>
           <div>
             <label className="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-1">Starting From</label>
             <input
               type="date"
-                  value={startDate}
+              value={entry.startDate}
-                  onChange={(e) => setStartDate(e.target.value)}
+              onChange={e => onChange({ startDate: e.target.value })}
               className="w-full px-4 py-3 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-700 text-gray-900 dark:text-gray-100 focus:ring-2 focus:ring-indigo-500 outline-none"
             />
           </div>
         </div>
       )}
 
-          {/* Times picker — hidden for as_needed */}
+      {entry.frequency !== 'as_needed' && (
-          {frequency !== 'as_needed' && (
         <div>
           <div className="flex items-center justify-between mb-1">
             <label className="block text-sm font-medium text-gray-700 dark:text-gray-300">Times</label>
@@ -214,22 +193,19 @@ export default function NewMedicationPage() {
               + Add Time
             </button>
           </div>
-              {frequency === 'daily' && (
-                <p className="text-xs text-gray-400 dark:text-gray-500 mb-2">Add multiple times for 2x, 3x, or more doses per day</p>
-              )}
           <div className="space-y-2">
-                {times.map((time, index) => (
+            {entry.times.map((time, i) => (
-                  <div key={index} className="flex gap-2">
+              <div key={i} className="flex gap-2">
                 <input
                   type="time"
                   value={time}
-                      onChange={(e) => handleTimeChange(index, e.target.value)}
+                  onChange={e => handleTimeChange(i, e.target.value)}
                   className="flex-1 px-4 py-3 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-700 text-gray-900 dark:text-gray-100 focus:ring-2 focus:ring-indigo-500 outline-none"
                 />
-                    {times.length > 1 && (
+                {entry.times.length > 1 && (
                   <button
                     type="button"
-                        onClick={() => handleRemoveTime(index)}
+                    onClick={() => handleRemoveTime(i)}
                     className="text-red-500 dark:text-red-400 px-3"
                   >
                     Remove
@@ -241,13 +217,114 @@ export default function NewMedicationPage() {
         </div>
       )}
     </div>
+  );
+}
+
+export default function NewMedicationPage() {
+  const router = useRouter();
+  const [entries, setEntries] = useState<MedEntry[]>([blankEntry()]);
+  const [isLoading, setIsLoading] = useState(false);
+  const [error, setError] = useState('');
+
+  const updateEntry = (index: number, updates: Partial<MedEntry>) => {
+    setEntries(prev => prev.map((e, i) => (i === index ? { ...e, ...updates } : e)));
+  };
+
+  const removeEntry = (index: number) => {
+    setEntries(prev => prev.filter((_, i) => i !== index));
+  };
+
+  const handleSubmit = async (e: React.FormEvent) => {
+    e.preventDefault();
+
+    for (let i = 0; i < entries.length; i++) {
+      const entry = entries[i];
+      if (!entry.name.trim() || !entry.dosage.trim()) {
+        setError(`Medication ${i + 1}: name and dosage are required`);
+        return;
+      }
+      if (entry.frequency === 'specific_days' && entry.daysOfWeek.length === 0) {
+        setError(`Medication ${i + 1}: select at least one day of the week`);
+        return;
+      }
+    }
+
+    setIsLoading(true);
+    setError('');
+
+    try {
+      for (const entry of entries) {
+        await api.medications.create({
+          name: entry.name,
+          dosage: entry.dosage,
+          unit: entry.unit,
+          frequency: entry.frequency,
+          times: entry.frequency === 'as_needed' ? [] : entry.times,
+          ...(entry.frequency === 'specific_days' && { days_of_week: entry.daysOfWeek }),
+          ...(entry.frequency === 'every_n_days' && {
+            interval_days: entry.intervalDays,
+            start_date: entry.startDate,
+          }),
+        });
+      }
+      router.push('/dashboard/medications');
+    } catch (err) {
+      setError((err as Error).message || 'Failed to add medication');
+    } finally {
+      setIsLoading(false);
+    }
+  };
+
+  const count = entries.length;
+
+  return (
+    <div className="min-h-screen bg-gray-50 dark:bg-gray-950">
+      <header className="bg-white dark:bg-gray-900 border-b border-gray-200 dark:border-gray-700 sticky top-0 z-10">
+        <div className="flex items-center gap-3 px-4 py-3">
+          <button onClick={() => router.back()} className="p-1 text-gray-600 dark:text-gray-400">
+            <ArrowLeftIcon size={24} />
+          </button>
+          <h1 className="text-xl font-bold text-gray-900 dark:text-gray-100">Add Medications</h1>
+        </div>
+      </header>
+
+      <form onSubmit={handleSubmit} className="p-4 space-y-4">
+        {error && (
+          <div className="bg-red-50 dark:bg-red-900/30 text-red-600 dark:text-red-400 px-4 py-3 rounded-lg text-sm">
+            {error}
+          </div>
+        )}
+
+        {entries.map((entry, index) => (
+          <MedCard
+            key={entry.id}
+            entry={entry}
+            index={index}
+            total={count}
+            onChange={updates => updateEntry(index, updates)}
+            onRemove={() => removeEntry(index)}
+          />
+        ))}
+
+        <button
+          type="button"
+          onClick={() => setEntries(prev => [...prev, blankEntry()])}
+          className="w-full flex items-center justify-center gap-2 py-3 border-2 border-dashed border-indigo-300 dark:border-indigo-700 rounded-xl text-indigo-600 dark:text-indigo-400 font-medium hover:border-indigo-400 dark:hover:border-indigo-600 transition-colors"
+        >
+          <PlusIcon size={18} />
+          Add Another Medication
+        </button>
 
         <button
           type="submit"
           disabled={isLoading}
           className="w-full bg-indigo-600 text-white font-semibold py-4 rounded-xl hover:bg-indigo-700 disabled:opacity-50"
         >
-          {isLoading ? 'Adding...' : 'Add Medication'}
+          {isLoading
+            ? 'Adding...'
+            : count === 1
+            ? 'Add Medication'
+            : `Add ${count} Medications`}
         </button>
       </form>
     </div>

synculous-client/src/app/dashboard/routines/new/page.tsx

@@ -50,6 +50,9 @@ export default function NewRoutinePage() {
   const [scheduleDays, setScheduleDays] = useState<string[]>(['mon', 'tue', 'wed', 'thu', 'fri', 'sat', 'sun']);
   const [scheduleTime, setScheduleTime] = useState('08:00');
   const [scheduleRemind, setScheduleRemind] = useState(true);
+  const [scheduleFrequency, setScheduleFrequency] = useState<'weekly' | 'every_n_days'>('weekly');
+  const [scheduleIntervalDays, setScheduleIntervalDays] = useState(2);
+  const [scheduleStartDate, setScheduleStartDate] = useState(() => new Date().toISOString().split('T')[0]);
 
   const toggleDay = (day: string) => {
     setScheduleDays(prev =>
@@ -128,11 +131,16 @@ export default function NewRoutinePage() {
         });
       }
 
-      if (scheduleDays.length > 0) {
+      if (scheduleFrequency === 'every_n_days' || scheduleDays.length > 0) {
         await api.routines.setSchedule(routine.id, {
           days: scheduleDays,
           time: scheduleTime,
           remind: scheduleRemind,
+          frequency: scheduleFrequency,
+          ...(scheduleFrequency === 'every_n_days' && {
+            interval_days: scheduleIntervalDays,
+            start_date: scheduleStartDate,
+          }),
         });
       }
 
@@ -227,6 +235,56 @@ export default function NewRoutinePage() {
         <div className="bg-white dark:bg-gray-800 rounded-xl p-4 shadow-sm space-y-4">
           <h2 className="text-lg font-semibold text-gray-900 dark:text-gray-100">Schedule <span className="text-sm font-normal text-gray-400">(optional)</span></h2>
 
+          {/* Frequency selector */}
+          <div className="flex gap-2">
+            <button
+              type="button"
+              onClick={() => setScheduleFrequency('weekly')}
+              className={`flex-1 px-3 py-2 rounded-lg text-sm font-medium border transition-colors ${
+                scheduleFrequency === 'weekly' ? 'bg-indigo-600 text-white border-indigo-600' : 'bg-white dark:bg-gray-700 text-gray-700 dark:text-gray-300 border-gray-300 dark:border-gray-600'
+              }`}
+            >
+              Weekly
+            </button>
+            <button
+              type="button"
+              onClick={() => setScheduleFrequency('every_n_days')}
+              className={`flex-1 px-3 py-2 rounded-lg text-sm font-medium border transition-colors ${
+                scheduleFrequency === 'every_n_days' ? 'bg-indigo-600 text-white border-indigo-600' : 'bg-white dark:bg-gray-700 text-gray-700 dark:text-gray-300 border-gray-300 dark:border-gray-600'
+              }`}
+            >
+              Every N Days
+            </button>
+          </div>
+
+          {scheduleFrequency === 'every_n_days' ? (
+            <div className="space-y-3">
+              <div>
+                <label className="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-1">Repeat every</label>
+                <div className="flex items-center gap-2">
+                  <input
+                    type="number"
+                    min={2}
+                    max={365}
+                    value={scheduleIntervalDays}
+                    onChange={(e) => setScheduleIntervalDays(Math.max(2, Number(e.target.value)))}
+                    className="w-20 px-3 py-2 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-700 text-gray-900 dark:text-gray-100 focus:ring-2 focus:ring-indigo-500 outline-none"
+                  />
+                  <span className="text-sm text-gray-600 dark:text-gray-400">days</span>
+                </div>
+              </div>
+              <div>
+                <label className="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-1">Starting from</label>
+                <input
+                  type="date"
+                  value={scheduleStartDate}
+                  onChange={(e) => setScheduleStartDate(e.target.value)}
+                  className="w-full px-4 py-3 border border-gray-300 dark:border-gray-600 rounded-lg bg-white dark:bg-gray-700 text-gray-900 dark:text-gray-100 focus:ring-2 focus:ring-indigo-500 outline-none"
+                />
+              </div>
+            </div>
+          ) : (
+            <>
               {/* Quick select buttons */}
               <div className="flex gap-2">
                 <button
@@ -277,6 +335,8 @@ export default function NewRoutinePage() {
                   ))}
                 </div>
               </div>
+            </>
+          )}
 
           <div>
             <label className="block text-sm font-medium text-gray-700 dark:text-gray-300 mb-1">Time</label>

synculous-client/src/app/dashboard/settings/page.tsx

@@ -396,14 +396,24 @@ export default function SettingsPage() {
               </button>
             </div>
             {notif.discord_enabled && (
+              <div className="space-y-1">
                 <input
                   type="text"
-                placeholder="Your Discord user ID"
+                  placeholder="Your Discord user ID (numbers only)"
                   value={notif.discord_user_id}
-                onChange={(e) => setNotif({ ...notif, discord_user_id: e.target.value })}
+                  onChange={(e) => {
+                    const val = e.target.value;
+                    if (val === '' || /^\d+$/.test(val)) {
+                      setNotif({ ...notif, discord_user_id: val });
+                    }
+                  }}
                   onBlur={() => updateNotif({ discord_user_id: notif.discord_user_id })}
                   className="w-full px-3 py-2 text-sm border border-gray-200 dark:border-gray-600 rounded-lg focus:outline-none focus:ring-2 focus:ring-indigo-500 focus:border-transparent text-gray-900 dark:text-gray-100 placeholder-gray-400 dark:placeholder-gray-500 bg-white dark:bg-gray-700"
                 />
+                <p className="text-xs text-gray-500 dark:text-gray-400">
+                  Enable Developer Mode in Discord, right-click your profile, and copy User ID
+                </p>
+              </div>
             )}
           </div>
         </div>
@@ -831,7 +841,7 @@ export default function SettingsPage() {
                     />
                     <select
                       value={newContact.contact_type}
-                      onChange={(e) => setNewContact({ ...newContact, contact_type: e.target.value })}
+                      onChange={(e) => setNewContact({ ...newContact, contact_type: e.target.value, contact_value: '' })}
                       className="w-full px-3 py-2 text-sm border border-gray-200 dark:border-gray-600 rounded-lg text-gray-900 dark:text-gray-100 bg-white dark:bg-gray-800"
                     >
                       <option value="discord">Discord</option>
@@ -840,9 +850,18 @@ export default function SettingsPage() {
                     </select>
                     <input
                       type="text"
-                      placeholder={newContact.contact_type === 'discord' ? 'Discord User ID' : newContact.contact_type === 'email' ? 'Email address' : 'Phone number'}
+                      placeholder={newContact.contact_type === 'discord' ? 'Discord User ID (numbers only)' : newContact.contact_type === 'email' ? 'Email address' : 'Phone number'}
                       value={newContact.contact_value}
-                      onChange={(e) => setNewContact({ ...newContact, contact_value: e.target.value })}
+                      onChange={(e) => {
+                        const val = e.target.value;
+                        if (newContact.contact_type === 'discord') {
+                          if (val === '' || /^\d+$/.test(val)) {
+                            setNewContact({ ...newContact, contact_value: val });
+                          }
+                        } else {
+                          setNewContact({ ...newContact, contact_value: val });
+                        }
+                      }}
                       className="w-full px-3 py-2 text-sm border border-gray-200 dark:border-gray-600 rounded-lg text-gray-900 dark:text-gray-100 bg-white dark:bg-gray-800"
                     />
                     <div className="flex items-center justify-between">