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Here’s why I won’t be switching on auto-deleting Siri chats
Ben Lovejoy · 2026-05-18 · via 9to5Mac
Here's why I won't be switching on auto-deleting Siri chats | A still from an Apple keynote on the new Siri

Whenever the new Siri finally launches, it’s going to be the most privacy-respecting AI chatbot out there, with an additional privacy feature reported yesterday.

We already knew that Apple’s agreement with Google will mean that Siri is not allowed to be used to train the Gemini model, and Bloomberg is now reporting an option to automatically delete our Siri conversations

While the new Siri will be powered by Google’s Gemini, it won’t be running on Google servers. Apple has said that it will instead run AI functions on-device wherever possible and the Gemini model on its own Private Cloud Compute servers where required. Outgoing CEO Tim Cook said at the time:

“We believe that we can unlock a lot of experiences and innovate in a key way due to the collaboration. We’ll continue to run on the device and run in Private Cloud Compute, and maintain our industry-leading privacy standards in doing so.“

Yesterday’s report says that the new Siri app will offer us the option of having our chats automatically deleted afterwards.

Another privacy win with the new Siri app will be auto-deleting conversation history. On the Messages app, you can set your conversation history to automatically delete after 30 days or a year, or leave them indefinitely. The same options will exist in the new Siri app.

That sounds good, and I do think it’s a positive thing that the option will be available – but I won’t be enabling it myself. That’s because AI chatbots learn from the history of all our chats, and that context can be extremely useful in our future interactions.

Claude is my current AI of choice, and I’ve trained it both explicitly and implicitly to reflect my own preferences. I’ve given it a number of standing instructions – for example, to be succinct, to use bullet points wherever possible, to avoid flowery language, to refrain from sycophancy, and to always include links to its sources of factual information. Additionally, when it answers a question in a style I like, I give it feedback on this and it has definitely learned from this practice.

There have been other examples when Claude has used contextual knowledge it has about me in order to tailor its responses. These aren’t things I’ve explicitly told it, but rather information it has gleaned from previous questions I have asked and from web searches it has carried out in response to my queries. There have been a good number of occasions on which Claude has intelligently used context like this when answering my questions.

For this reason, I won’t be automatically deleting any of my Siri chats. There’s always the option to manually delete individual chats if you have concerns about Siri retaining sensitive data from particular sessions. I’ve also done this for chat sessions used when I’m assisting a friend with something, and I don’t want it to get confused by thinking that context relates to me.

As an aside, one thing I very quickly learned with AI chatbots is that you should start a new conversation for each topic. If you don’t, then it processes all of the content of the current chat each time you add something to it, and that uses many more tokens. It’s also much easier to refer back to previous sessions and to resume them when required if each is a distinct chat in your sidebar or history. Claude generally does a good job at giving each chat a sensible name.

That will be my approach, then – how about you? Please share your thoughts in the comments.

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