Inward2Onward · Amplify

Calendar Countermeasure Automation

A redundant reminder system so a required training is never again missed for lack of a reminder. Reads the Amplify calendar, then pushes the day, tomorrow, and the week ahead to email and text — with native calendar reminders underneath as the guarantee.

Live & tested — August 5, 2026

System status

  • Native calendar reminders — Email 24h + Popup 60m on ej@amplifyai.com. Tested, firing.
  • Email — to ej@inward2onward.com via Resend. Delivery confirmed in logs.
  • iMessage — to 623-272-8066 from EJ's Mac. Tested, arriving.
  • Gmail forward — native reminder emails routed amplify → inward2onward. Verified.
  • Four scheduled automations — running on schedule (America/Phoenix).

Defense in depth — no single point of failure

Layer 1 · Guarantee

Native calendar reminders

Email 24h + popup 60m, fired by Google and your phone — independent of any automation or the Mac being on.

Layer 2 · Awareness

Daily & weekly digests

Morning agenda, evening tomorrow-preview, Friday week-ahead. Email + iMessage. Required trainings flagged at top.

Layer 3 · Watchdog

Weekly health check

Every Monday, confirms the digests ran, the calendar is readable, and both channels are alive — alerts if not.

How it flows

Source
Google Calendar
ej@amplifyai.com
Engine
Cowork Scheduled Tasks
4 jobs · Phoenix time
Email
Resend
ej@inward2onward.com
Text
iMessage
623-272-8066

The four automations

TaskWhen (America/Phoenix)Sends
morning-agenda-digestDaily ~6:10 AMToday's schedule → email + iMessage
end-of-day-tomorrow-previewDaily ~5:02 PMTomorrow's schedule → email + iMessage
week-ahead-digestFri ~4:01 PMNext 7 days → email + iMessage
reminder-system-health-checkMon ~7:06 AMWatchdog → alerts if anything broke

Tech stack — in use

ComponentRoleConfigStatus
Cowork — Scheduled TasksOrchestrationCron, Phoenix time; runs while app openLive
Google Calendar (MCP)Data sourceej@amplifyai.com (owner)Verified
Calendar native notificationsReminder — Layer 1Email 24h + Popup 60mTested
Resend (MCP)Email deliveryreminders@inward2onward.com (verified)Live
iMessage connectorText deliverysend_imessage → +16232728066, from MacTested
Gmail forwarding filter (amplify)Email routingcalendar-notification@google.com → inward2onwardVerified

Evaluated but not used

ComponentConsidered forNot used because
Twilio (MCP)Programmatic SMSConnector is documentation-only; cannot send Dropped
T-Mobile email-to-SMS gatewayFree SMS via ResendReturned delivery_delayed; replaced by iMessage Dropped
Gmail (MCP)Email sendCan only draft, not send Dropped

The one habit that keeps it working

Keep the Mac awake & Messages signed in around run times

6 AM · 5 PM · Friday 4 PM. iMessage sends from your Mac, so if it's asleep the text won't fire. Email still queues, and the native calendar reminders run independently — so you're covered either way, but a live Mac gets you all channels.

Project documents

  • PRD-Meeting-Session-Reminder-Automation.md — design, architecture, defense-in-depth, stress test
  • SOP-Reminder-Automation.md — runbook, troubleshooting, metrics (tech stack in Appendix A)
  • Tech-Stack-Reminder-Automation.md — standalone tech stack
  • Brief-to-Kayla-Countermeasure.md — accountability brief, ready to send
  • START_HERE.md — one-page index & current status