| Connected inbox (automatic extraction) | ✓ Connect once, events picked up for you Gmail, Outlook, iCloud, Yahoo, AOL - no prompting needed | ◐ Manual forwarding or chat commands Relied on forwarded emails or conversational texting to process tasks |
| PDF newsletter parsing | ✓ Parses attached PDFs and tables Extracts dates, times, and notes from complex school newsletters | ◐ Limited document parsing Struggled with multi-page schedules and embedded timetable tables |
| WhatsApp group monitoring | ✓ Linked device Monitors selected parent group chats quietly | ✗ Not available Operated primarily via SMS and web text interfaces |
| Photo and letter extraction | ✓ Built in Flyers, timetables, PDFs, and paper letters | ◐ Photo capture via MMS Supported sending photos over text message |
| Calendar connection | ✓ Google, Outlook, Apple Calendar Events land directly on your existing phone calendar | ✓ Calendar sync Synced confirmed events to Google and Apple calendars |
| Parent interaction effort | ✓ Zero ongoing effort Runs quietly in the background without daily messaging | ◐ Chat-driven interaction Required continuous texting, replying, and prompt follow-up |
| Proactive reminders | ✓ Days in advance Advance notice for kit preparation, forms, and schedule changes | ◐ Conversational check-ins Sent periodic SMS check-ins and digest messages |
| Second parent's inbox | ✓ Connected on Family plan Both parents connect separate inboxes under one subscription | ◐ Shared household SMS Allowed adding partners to text threads |
| Privacy and data verification | ✓ CASA2 certified, zero human reviewers Processed ephemerally in memory, never stored, no human reading your emails | ◐ Human reviewers in the loop Relied on third-party parent reviewers to inspect and verify texted entries |
| Pricing | ✓ £6.99/mo or £59.99/yr Family covers two accounts at £9.99/mo or £99.99/yr. 7-day free trial | ✗ Discontinued ($40 to $100/mo) Milo charged $40/mo for Sidekick and $100/mo for Pilot before shutting down |
| Platform | ✓ iOS and Android Native apps with home screen widgets and calendar integration | ◐ SMS and web Operated through text messaging rather than a dedicated native app |
Gold 2026