AgentComparison
Ollie · product · family assistant by iMessage and SMS

Ollie

A text-first family assistant for calendar, inbox and school messages, billed by messages.

Group: Personal agents you message

Ollie is a text-first family assistant that watches your calendar and inbox, answers questions such as what is on this week and tells you what matters. You text a number over iMessage or SMS and connect Google or Outlook through standard OAuth consent.

Documentation researched, not testedChecked 1 October 2026Vendor documentation, not a test

The decision in plain English

Ollie bills by messages: a free plan with 50 messages a month, then $25 a month for 150 and $100 a month for 1,000, plus a small daily free allowance. TechCrunch says Ollie is SOC 2 compliant; we did not find that on the vendor pages we read, so it is not stated here as fact.

Best fit

Families who want a calendar-and-inbox assistant they text.

Poor fit

Anyone who needs a published SOC 2 report from the vendor's own site before connecting an inbox.

Documented capabilities

Vendor statements, not verified task outcomes.

  • Watches calendar and inbox and texts what matters Source · checked 2026-10-03
  • Works over iMessage or SMS with Google or Outlook connections Source · checked 2026-10-03

Permissions and human control

  • Ollie's FAQ says calendar and email access is granted through standard OAuth consent screens and that it never sees or stores your Google or Microsoft password.

Documented controls do not prove that an agent always follows them.

Limits and open questions

  • Billing is by Ollie replies; plans cap messages per month
  • SOC 2 claim comes from TechCrunch only; not verified by us
  • Messages are sent to Anthropic, Google and OpenAI models via commercial APIs (vendor FAQ)
  • Described by the vendor; not tested by AgentComparison

Privacy and security

Ollie's FAQ says your data is used only to provide the service and is not shared with other users, that models come from Anthropic, Google and OpenAI via commercial APIs whose terms say inputs are not used for training, and that Ollie uses layered security including OAuth.

Common questions about Ollie

What is Ollie for?

Families who want a calendar-and-inbox assistant they text. The vendor describes it as: Ollie is a text-first family assistant that watches your calendar and inbox, answers questions such as what is on this week and tells you what matters. You text a number over iMessage or SMS and connect Google or Outlook through standard OAuth consent.

Who should look elsewhere?

Anyone who needs a published SOC 2 report from the vendor's own site before connecting an inbox.

How much does Ollie cost?

ollie.ai/pricing lists Free ($0), $25 a month and $100 a month plans by monthly message allowance.

What can it access and what needs my approval?

Ollie's FAQ says calendar and email access is granted through standard OAuth consent screens and that it never sees or stores your Google or Microsoft password.

What happens to my data?

Ollie's FAQ says your data is used only to provide the service and is not shared with other users, that models come from Anthropic, Google and OpenAI via commercial APIs whose terms say inputs are not used for training, and that Ollie uses layered security including OAuth.

Has AgentComparison tested it?

No. This record is built from the vendor's own documentation, checked 2026-10-03. Vendor claims are attributed, not confirmed.

How to evaluate Ollie yourself

  1. Pick one low-risk task that matches its documented capabilities: watches calendar and inbox and texts what matters.
  2. Write the expected output and what counts as failure before you start.
  3. Connect the minimum access needed, and check approval settings first.
  4. Run it twice and compare, then review every action it took.
  5. Check cost after any free allowance. Unknown price is not free.

Related

Sources and history

Change history

Documentation overview expanded with current pricing/access sources. No hands-on results claimed.

Report a correction