Perhaps optionally. Like modes for "just keep it on this device" and "keep it on this device but I'm a server and will provide it to other devices when asked". Assume a secure connection between the personal server and all one's edge devices such that clients act more like remote controls for the "main agent" on the server.

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Yup. This is definitely an option for syncing chat transcripts. And it would be implemented at the client/application layer.