Apple is expected to launch a new version of Siri in September with iOS 27, a move that would make it the world’s most widely installed AI chatbot from day one because it will come preloaded on hundreds of millions of iPhones. The oldest supported devices mentioned in the report are the iPhone 15 Pro models.
Yet Bloomberg reporter Natalie Lung, after testing the system, said the new Siri still trails ChatGPT by a wide margin in pure conversation quality, even though it is much better at reading on-device content and understanding what is on the screen.
Siri’s advantage lies in device context
Bloomberg said the upgraded Siri can, for the first time, generate tailored replies based on a user’s emails, text messages, notes and files. It can also interpret whatever is visible on the screen. That includes spreadsheets, documents and even crossword puzzles, where it can offer clues directly.
This is presented as Siri’s main strength. Its edge is not chat fluency on its own, but the ability to combine personal device data with live screen context when responding to a request.
There is a cost to that. On first launch, the new Siri may need hours, or even days, to re-index content stored on the device before it can accurately pull answers from information saved years earlier.
Real-time third-party data remains limited
The report said Siri still cannot access real-time information from third-party apps, such as live flight or hotel prices from travel comparison services. Bloomberg noted that ChatGPT had already rolled out that type of integration late last year.
Without those outside connections, users currently have to upload photos and documents manually if they want to give Siri more reference material.
Bloomberg also found that Siri is not positioning itself as a companion or therapist. When asked about personal troubles, it says it is a virtual assistant and cannot talk like a human friend, then suggests speaking with family, friends or a professional. It takes a similar line on health questions. Even though Apple has fitness data from the Apple Watch, Siri still says it is not a doctor and recommends consulting medical professionals.
Easier to summon, but conversation remains turn-based
On access, Siri keeps a native advantage. Users can open it through a new standalone app, say “Hey Siri,” swipe down from the top of the screen, or long-press the Siri button. ChatGPT, as a third-party app, must be triggered through a customized action button, Control Center or a lock-screen shortcut.
That said, Bloomberg was blunt about the current speaking experience. Siri still works largely in a one-question, one-answer format, and users cannot interrupt it mid-response. That conversational feature only entered public beta in July and is not expected to be fully available until the fall.
ChatGPT leans on voice and workflow tools
OpenAI’s strongest card in the comparison is voice. Its latest voice model, GPT-Live, allows back-and-forth speech that is no longer strictly turn-taking. It can listen while speaking and even insert brief acknowledgments while the user is still talking, making the exchange feel closer to a live human conversation.
The paid ChatGPT Work offering goes further by bringing integrations such as the Codex coding tool and Google Drive into the desktop app. Bloomberg said it can produce slide decks, websites and even edit content directly based on files stored on a computer within minutes. Those functions have now been opened to mobile and browser versions as well.
That setup also comes with trade-offs. Heavy usage can quickly consume allowance limits, and projects are not yet fully synchronized between desktop and mobile devices. Ty Geri, OpenAI’s product manager for ChatGPT Work, said in an interview, “This is a pain point we want to solve,” adding that most knowledge work already happens in the cloud, which is why the desktop experience was separated for now.
Distribution versus capability
Bloomberg framed the competition as a contest between distribution and capability. Siri wins on default installation and on knowing the user better through on-device data. ChatGPT leads on iteration speed and the natural feel of its voice interaction.
For Apple users, this is an upgrade that had been promised since 2024 and is only now nearing release after a two-year wait. As long as the iPhone chip is new enough, the new Siri could, for the first time, put years of accumulated personal device data to practical use. It may not be the strongest at casual conversation, but the report argues that no rival is better placed to understand a user’s day-to-day context on Apple hardware.
OpenAI, however, is still moving quickly. The report ends with a simple question: which product can keep users coming back more often. Bloomberg suggests the answer may not take long to emerge.