DailyRoundup

DailyRoundup app icon and name over a gradient background

DailyRoundup

An iOS and macOS app that syncs tasks from Trello into Apple Reminders. A self-hosted sync broker running on any always-on Linux host receives Trello webhook events and queues changes for the app to pull.

Key features:

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Table of Contents

Usage

iOS App

  1. Open the app and tap the gear icon to open Settings.
  2. Enter the server URL and tap Connect to Server… to link your account (see Connecting Trello for full setup details).
  3. Tap Create Synced List… to create a linked Trello list and Reminders list pair.
  4. Create or update cards in the Trello list. The next time you open DailyRoundup, it pulls all pending changes and applies them to Reminders automatically.

The main view shows all synced reminder lists and items, with sync status displayed below the navigation title and any unresolved conflicts or potential duplicates listed as tappable rows. Tapping a task, conflict, or duplicate row opens its details in a stackable slide-up view (the same presentation style as Settings); task completion is still toggled by tapping the row’s checkbox. Pull down on the list to trigger a manual sync. Settings are accessible via the gear icon in the toolbar.

macOS App

On macOS, DailyRoundup runs as a regular dock app with the same single-view layout as iOS — synced lists and tasks with inline sync status. A menu bar icon provides quick access to sync status, pending change count, conflict count, a Sync Now button, and Settings. The app syncs continuously in the background — it triggers a sync whenever Reminders changes, on a 60-second fallback timer, and immediately after the Mac wakes from sleep.

roundup-server

Start the server for development:

cd roundup-server
python -m dailyroundup.app

Start with gunicorn for production:

gunicorn "dailyroundup.app:create_app()" --bind 0.0.0.0:5000 --workers 4 --timeout 60

Installation and Configuration

App (iOS / macOS)

Requirements: Xcode 26+, iOS 26+, macOS 26+, an Apple Developer account

  1. Clone the repository:

    git clone git@github.com:dcwalker/DailyRoundup.git
cd DailyRoundup

  2. Copy the Xcode config sample and add your development team ID:

    cp Local.xcconfig.sample Local.xcconfig
# Edit Local.xcconfig and set DEVELOPMENT_TEAM to your Apple Developer Team ID

  3. Open the project in Xcode and run on a device or simulator:

    open DailyRoundup.xcodeproj

  4. On first launch, grant Reminders and Notifications access when prompted.

  5. Tap the gear icon, enter your server URL, and tap Connect to Server… to complete setup (see Connecting Trello).

roundup-server

Requirements: Python 3.12+

  1. Clone the repository and change into this directory:

    cd roundup-server

  2. Install dependencies:

    pip install -r requirements.txt

  3. Copy env.sample to .env and fill in all required values:

    cp env.sample .env
$EDITOR .env

  4. Run database migrations:

    python migrate.py

  5. Start the server (see Usage).

Running Behind a Reverse Proxy (HTTPS)

The server must be reachable over HTTPS for Trello webhooks to fire. Use nginx or Caddy as a TLS-terminating reverse proxy in front of gunicorn.

Configuring APNs Push Notifications

Silent background-sync pushes are optional. The server starts and operates normally without them — devices fall back to polling whenever the app is opened. To enable near-real-time sync (Trello change → silent push → Reminders update within seconds):

  1. Generate an APNs key in the Apple Developer portal:
    • Go to Certificates, Identifiers & Profiles → Keys
    • Create a new key with the Apple Push Notifications service (APNs) capability enabled
    • Download the .p8 file (it can only be downloaded once; store it securely on the server)
  2. Note your credentials:
    • Key ID: the 10-character identifier shown on the key detail page
    • Team ID: the 10-character identifier shown in the top-right of the portal
  3. Set the environment variables in your .env file (see Environment Variables):
    • APNS_KEY_ID and APNS_TEAM_ID from the values above
    • APNS_BUNDLE_ID: the app’s bundle ID (e.g. dev.dcwalker.DailyRoundup)
    • APNS_PRIVATE_KEY: the full contents of the .p8 file, including the -----BEGIN PRIVATE KEY----- and -----END PRIVATE KEY----- lines

  4. Set APNS_USE_SANDBOX=1 if testing with a development or Ad Hoc build. Omit it (or set to 0) for App Store and TestFlight builds.

  5. Restart the server so it picks up the new variables.

If any of the four required variables (APNS_KEY_ID, APNS_TEAM_ID, APNS_BUNDLE_ID, APNS_PRIVATE_KEY) are absent, APNs calls are silently skipped and a DEBUG-level log message is emitted.

Connecting Trello

The app connects to Trello via OAuth during initial setup. You will need a Trello API Key and Webhook Secret before you begin.

  1. Get a Trello API Key from the Trello Power-Ups admin page. Create a new Power-Up (or use an existing one) and copy the API Key from its API Key tab.

  2. Generate a Webhook Secret — any long random string. The server uses this to verify HMAC-SHA1 signatures on incoming Trello webhook events. You can generate one with:

    openssl rand -hex 32
  3. In the app, tap the gear icon to open Settings, then tap Connect to Server…. Fill in:
    • Server URL: your roundup-server’s HTTPS URL
    • Bootstrap Token: the DAILYROUNDUP_BOOTSTRAP_TOKEN value from your server’s .env file
    • Trello API Key: the key from step 1
    • Webhook Secret: the secret from step 2

  4. Tap Connect. The app creates your account on the server and immediately opens a Trello OAuth page in an in-app browser. Sign in to Trello and tap Allow to grant DailyRoundup read/write access. The OAuth token is sent back to the app automatically and persisted on the server.

  5. Once connected, the bootstrap token is no longer needed — the app stores a permanent per-account auth token in iCloud Keychain.

If you already have a permanent auth token (e.g. from a previous setup or another device), expand I already have a token in the connect sheet and paste the token directly. This skips the bootstrap token and OAuth steps.

To re-authorize Trello (e.g. if you revoked access), tap Authorize Trello in the Trello Configuration section of Settings. This opens the same OAuth flow and updates the token on the server.

For a detailed sequence diagram showing every API call during setup and what the server stores at each step, see Setup Flow Details.

Operations

Health monitoring via GET /health and GET /dailyroundup/status, optional Datadog usage metrics over DogStatsD, GitHub Actions alerting on deployment failures, common troubleshooting scenarios (auth errors, missing webhooks, APNs configuration), and server log access via journalctl. See Operations for full details.

Card Action Scheduler

The card-action scheduler (issue #334) is a background daemon thread inside roundup-server that drives the account-wide “move cards by date” feature:

The configuration is account-wide and applies to every synced list on the account’s trello_board_id; synced lists on any other board are skipped (with a WARNING log) because Trello’s update_card cannot cross boards. The two destination list IDs must reference open Trello lists on the same board.

The scheduler also drives the per-list pin to top feature, enabled with move_pinned_to_top_enabled. The 📌 prefix on a card’s name is the source of truth: when the toggle is on, cards whose name starts with 📌 are kept at the top of the Trello list, ordered by dateLastActivity descending, while non-pinned cards keep their relative order. Reordering is event-driven on Trello webhook events under the sync_lease, logging at INFO for each reorder (touched list, pinned-card count, and cards moved), with startup and daily reconcile passes that correct any drift left by missed webhook events and log at WARN when they do. A 📌 card without a due date can also surface on opted-in devices as a title-only Live Activity for a configurable window; a 📌 card that has a due date keeps the existing remind-to-due Live Activity.

The scheduler is event-driven: it maintains a card_action_index table populated from Trello webhook events and from configuration changes, sleeps until the earliest indexed wake-up moment, and acquires the global sync_lease before acting so concurrent writers cannot race. It also runs a reconciliation pass on startup and on a daily cadence that walks every applicable list, compares indexed timestamps against current Trello state, corrects any drift, and logs discrepancies at WARNING so missed webhook events stay visible to operators.

Configuration is stored on the accounts table and is set via PUT /dailyroundup/account. Set DAILYROUNDUP_SCHEDULER_ENABLED=0 to disable the scheduler.

Technical Details

System architecture diagrams, webhook ingest and foreground sync flow sequences, module structure tables for the iOS/macOS app and roundup-server, and the sixteen-table database schema. See Technical Details for full details.

Environment Variables

Variable Required Description
DAILYROUNDUP_BOOTSTRAP_TOKEN Yes (initial setup) One-time token used to create the first account via POST /dailyroundup/account. Once an account is created, the permanent per-account token is stored in iCloud Keychain and this variable is no longer needed.
DAILYROUNDUP_WEBHOOK_URL Yes Public HTTPS URL for the Trello webhook callback
DAILYROUNDUP_DB_PATH No Path to the SQLite database file (default: dailyroundup.db)
DAILYROUNDUP_HOST No Development server bind host (default: 0.0.0.0)
DAILYROUNDUP_PORT No Development server port (default: 5000)
DAILYROUNDUP_MAX_CONTENT_LENGTH No Maximum request body size in bytes (default: 8388608, i.e. 8 MB)
DAILYROUNDUP_SCHEDULER_ENABLED No Set to 0 to disable the card-action scheduler (default: enabled). See Card Action Scheduler.
DAILYROUNDUP_DRAIN_TIMEOUT No Seconds the deploy-drain step (drain.py) waits for in-flight sync jobs to finish before a restart (default: 30).
FLASK_DEBUG No Set to 1 for Flask debug mode (development only)
APNS_KEY_ID No* 10-character APNs key ID from the Apple Developer portal
APNS_TEAM_ID No* 10-character Team ID from the Apple Developer portal
APNS_BUNDLE_ID No* iOS/macOS app bundle ID (e.g. dev.dcwalker.DailyRoundup)
APNS_PRIVATE_KEY No* Full PEM contents of the .p8 file, including BEGIN/END PRIVATE KEY lines
APNS_USE_SANDBOX No Set to 1 to target the APNs sandbox; omit for production
HEALTHCHECK_URL No Base URL for the post-deployment health check script (default: http://127.0.0.1:5000)
HEALTHCHECK_TIMEOUT No Seconds to wait for the server to become ready during the health check (default: 30)
HEALTHCHECK_TOKEN No Per-account bearer token for the GET /dailyroundup/status check in healthcheck.py; if unset, that check is skipped
DD_AGENT_HOST No Datadog Agent host for DogStatsD usage metrics. When set, the server emits the counters described in Usage Metrics; when unset, metric emission is disabled and no socket is opened
DD_DOGSTATSD_PORT No DogStatsD UDP port (default: 8125); only used when DD_AGENT_HOST is set

* All four APNS_* variables must be set together to enable push notifications. If any are absent, APNs is disabled and the server logs a DEBUG message. See Configuring APNs Push Notifications for setup steps.

Trello credentials (trello_api_key, trello_token, trello_board_id) and the Webhook Secret (trello_webhook_secret) are stored per-account in the database and configured via the app’s Settings screen after account creation.

API Reference

POST /dailyroundup/account is protected by the DAILYROUNDUP_BOOTSTRAP_TOKEN environment variable. All other endpoints except GET /health and the Trello webhook endpoints require an Authorization header with the per-account bearer token returned when the account was created:

Authorization: Bearer <account-token>

See roundup-server/openapi.yaml for the full OpenAPI specification.

Method Path Description
GET /health Health check
GET /dailyroundup/status Account-scoped operational stats (sync list count, registered device count)
POST /dailyroundup/account Create a new account (requires bootstrap token)
GET /dailyroundup/account Get current account details
PUT /dailyroundup/account Update account settings (Trello credentials, webhook secret)
GET /dailyroundup/lists List all synced list pairs for this account
POST /dailyroundup/lists Create a new synced list pair
POST /dailyroundup/lists/merge Merge an existing Trello list and Reminders calendar into a synced pair
PATCH /dailyroundup/lists/{sync_list_id} Update list metadata
DELETE /dailyroundup/lists/{sync_list_id} Remove a synced list pair
POST /dailyroundup/lists/{sync_list_id}/reset Reset all sync state for a list
GET /dailyroundup/trello_boards List all Trello boards on the configured account
GET /dailyroundup/trello_lists List all Trello lists on the configured board
GET /dailyroundup/trello_cards List all cards in a Trello list
GET /dailyroundup/trello_test Test Trello API connectivity
GET /dailyroundup/changes Return pending Trello-side changes
POST /dailyroundup/changes/{change_id}/ack Acknowledge an applied change
POST /dailyroundup/sync Accept Reminders-side changes (returns 202 with job_id for async polling)
GET /dailyroundup/sync/jobs/{job_id} Poll for sync job status and results
GET /dailyroundup/sync/status Return per-list sync statistics
GET /dailyroundup/state Full state dump for initial sync or recovery
GET /dailyroundup/card_metadata Fetch labels, attachments, checklists, and custom fields for cards
POST /dailyroundup/devices Register a device APNs token
POST /dailyroundup/reconcile Reconcile sync_tasks against actual Trello cards (open and archived); emits delete changes for cards that were permanently deleted
GET /dailyroundup/potential-duplicates List unresolved potential duplicates
POST /dailyroundup/potential-duplicates/{id}/resolve Resolve a potential duplicate (merge or keep_both)
GET /dailyroundup/conflicts List all unresolved conflicts
POST /dailyroundup/conflicts/{conflict_id}/resolve Resolve a conflict
POST /dailyroundup/attachments/move-urls Batch-move URL link attachments into card descriptions and delete the attachments from Trello
DELETE /dailyroundup/account Delete account and all associated data
GET /dailyroundup/webhook/trello Trello webhook verification endpoint
POST /dailyroundup/webhook/trello Receive Trello webhook events

Permissions

Permission Access granted Required for
Reminders (EventKit) Read and write all reminder lists and items Displaying, creating, and updating reminders from Trello
iCloud Key-Value Store Read and write app-specific KV pairs in iCloud Syncing server URL, sync list IDs, and last sync timestamp across devices
iCloud Keychain Read and write a single Keychain item Storing the auth token securely across devices
Push Notifications (APNs) Receive remote notifications and notification actions Registering device tokens and delivering conflict-resolution alerts

Design Guidelines

The app follows Apple’s Human Interface Guidelines on both iOS and macOS. There are no custom colors, typefaces, or animation overrides — all controls use standard SwiftUI system components so the app adapts automatically to light/dark mode, Dynamic Type, and accessibility settings. On macOS, Forms use .formStyle(.grouped) for consistent grouped-section layout. New UI should use system-provided components and avoid hardcoded colors or custom interaction patterns unless a standard component cannot fulfill the requirement.

Documentation

Contributing

See CONTRIBUTING.md for coding standards, commit message format, and documentation guidelines. See AGENTS.md for AI-agent-specific directives.