This one is sad news. Ollie, the AI assistant families texted to keep the week together, is shutting down on November 6. Here is what happened, what Ollie was, and what to do before it goes.
What happened
On October 30, 2026, Ollie’s co-founder and CEO, Bill Lennon, announced on X: “This is a painful post to share. Today we’re announcing that we’re shutting down @heyollieai on November 6.” He went on: “I’m really proud of what we accomplished. We built an incredible personal assistant with a small team, and learned a ton.” The image with the post reads “A farewell to Ollie. Ollie is sunsetting on Nov. 6, 2026.”
In a follow-up post to users, he wrote: “To our users, thank you for supporting us over these last few years. We want to make this transition smooth. You should receive notifications from us on how to export your data and refunds we’ll be issuing. If you have any questions, please reach out to us at hello@ollie.ai”
What Ollie was
Ollie called itself “a family AI assistant you can simply text,” with no app to download: you texted it over iMessage or SMS, and could bring it into a group conversation with your family. Its homepage says it “brings together your calendars, emails, and to-dos, and texts you what matters,” with school emails, carpool reminders, a daily briefing, meal plans and grocery orders as the examples.
Parents loved it. Two weeks before the announcement, The New York Times told the story of Lisa Green, a pediatrics resident whose 5-year-old kept missing library-book days on a rotating kindergarten schedule. She photographed the schedule and gave it to Ollie, which now texts her to pack the book. Before that, she said, “all the balls I’m starting to drop feel like the glass ones.” In September, TechCrunch covered its $7.5 million seed round, raised largely from Khosla Ventures along with AI House, and its focus on privacy: Ollie didn’t ask for usernames or passwords to do its tasks, and TechCrunch called it “among the first mainstream, family-focused AI to achieve SOC 2 compliance.”
Ollie’s FAQ says it connected to Google or Outlook through their standard sign-in consent “so Ollie can view your schedule, create events, and triage email on your behalf.”
What happens to your plan
Ollie’s pricing page still listed three plans on October 30, 2026, priced by the number of messages Ollie sends you:
- Free: 50 messages a month, plus 6 free a day.
- Everyday: $25 a month for 150 messages, plus 10 free a day.
- Always-On: $100 a month for 1,000 messages, plus 15 free a day.
Ollie says it will issue refunds and tell each user how. Before November 6:
- Export your data when Ollie’s instructions arrive. Its FAQ lists conversations, meal plans, calendar details and email summaries among what it stores.
- Move anything dated after November 6 (reminders, carpools, appointments) onto your own calendar.
- Remove Ollie’s access to your email and calendar from your Google or Microsoft account settings once you have what you need.
- Write to hello@ollie.ai if a refund or export hasn’t arrived.
If some of what Ollie did was work email
Ollie was built for family life, and nothing replaces that one for one. If part of what you leaned on it for was keeping up with work email, that is the job alfred_ is built for.
alfred_ is an AI assistant for client-facing teams. It reads your email across up to six Gmail, Outlook and IMAP accounts, flags the emails that need your answer, and keeps one list of the replies you owe and the replies you’re waiting on. It sends a morning brief by email or text, and you can ask it for things by text. Nothing is sent until you approve it. Plans start at $29.99 a month. Other assistants you can text are in Best Ollie alternatives.
