Caddy is a personal AI assistant that lives inside iMessage on iPhone and RCS on Android, so there is no separate app or inbox to check . This launch extends that approach by bringing a richer interactive interface directly into the Messages thread and shipping a matching update to the Caddy app, so users can act on incoming information without context switching.
The headline additions focus on quick, in-thread actions. When a connected email arrives, Caddy texts the user with a one-tap option, and once tapped, Caddy drafts the reply . Users tell Caddy the outcome they want, it reads the connected Gmail thread, prepares a reply in iMessage, and waits for review before sending . A new Find My integration lets Caddy use the user's current location to suggest nearby restaurants, folding local recommendations into the same conversation that already handles email, calendar, and task triage.
Caddy was founded in 2025 by Rajiv Sancheti and Connor Waslo, is part of Y Combinator's Fall 2025 batch, and has five employees based in New York City . The launch matters for operators and founders who want an assistant that reaches them where they already read messages, rather than one more inbox to open, and it sharpens Caddy's positioning against other text-native AI agents by making approvals and location-aware suggestions a tap away.
Comments (11)
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Priya Nadkarni1d ago
iMessage as the UI is a bold choice. Curious what happens when Apple decides they want this exact feature next September.
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Kwame Oyelaran1d ago
The Find My plus restaurant suggestion flow is cute, but what stops it from pinging me a sushi spot while I'm literally at the dentist?
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Lena Voss1d ago
Launch video pacing was tight but the voiceover sounded like it was recorded inside a MacBook fan. Still watched it twice.
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mina1d ago
'Stay on top of work and life' is doing nothing for me. Try 'Caddy texts you back so you don't have to.'
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Tomás B.1d ago
Retention question: what's the week-4 number on texting-based assistants? Everyone I know eventually mutes the thread.
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Ravi S.1d ago
Building something adjacent in the calendar space and honestly the iMessage surface is the move I wish we'd committed to. Respect.
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sasha1d ago
Been '3 weeks from launching' my own assistant for 8 months. Seeing this live is motivating and also deeply upsetting.
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Yuki Matsuo1d ago
One-tap email replies via SMS is the kind of feature that lives or dies on how often the suggested reply is actually right. Rooting for the model.
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Oluchi A.1d ago
Shipped a one-tap reply inside a messaging surface at a Big Co in 2019 and leadership killed it for 'thread hygiene.' Glad someone finally did it.
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Fareed Khoury1d ago
Before I plug my inbox and location into a texting bot, where does the data live and who gets to read it when subpoenas show up?
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Deepa Varghese1d ago
Who's on the hiring side here? I know an iOS eng who has strong feelings about MessageKit and would probably work for espresso.
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Caddy is a personal AI assistant that lives inside iMessage on iPhone and RCS on Android, so there is no separate app or inbox to check . This launch extends that approach by bringing a richer interactive interface directly into the Messages thread and shipping a matching update to the Caddy app, so users can act on incoming information without context switching. The headline additions focus on quick, in-thread actions. When a connected email arrives, Caddy texts the user with a one-tap option, and once tapped, Caddy drafts the reply . Users tell Caddy the outcome they want, it reads the connected Gmail thread, prepares a reply in iMessage, and waits for review before sending . A new Find My integration lets Caddy use the user's current location to suggest nearby restaurants, folding local recommendations into the same conversation that already handles email, calendar, and task triage. Caddy was founded in 2025 by Rajiv Sancheti and Connor Waslo, is part of Y Combinator's Fall 2025 batch, and has five employees based in New York City . The launch matters for operators and founders who want an assistant that reaches them where they already read messages, rather than one more inbox to open, and it sharpens Caddy's positioning against other text-native AI agents by making approvals and location-aware suggestions a tap away.
Comments (11)
iMessage as the UI is a bold choice. Curious what happens when Apple decides they want this exact feature next September.
The Find My plus restaurant suggestion flow is cute, but what stops it from pinging me a sushi spot while I'm literally at the dentist?
Launch video pacing was tight but the voiceover sounded like it was recorded inside a MacBook fan. Still watched it twice.
'Stay on top of work and life' is doing nothing for me. Try 'Caddy texts you back so you don't have to.'
Retention question: what's the week-4 number on texting-based assistants? Everyone I know eventually mutes the thread.
Building something adjacent in the calendar space and honestly the iMessage surface is the move I wish we'd committed to. Respect.
Been '3 weeks from launching' my own assistant for 8 months. Seeing this live is motivating and also deeply upsetting.
One-tap email replies via SMS is the kind of feature that lives or dies on how often the suggested reply is actually right. Rooting for the model.
Shipped a one-tap reply inside a messaging surface at a Big Co in 2019 and leadership killed it for 'thread hygiene.' Glad someone finally did it.
Before I plug my inbox and location into a texting bot, where does the data live and who gets to read it when subpoenas show up?
Who's on the hiring side here? I know an iOS eng who has strong feelings about MessageKit and would probably work for espresso.