ChatGPT's new Mac plugin analyzed my iMessages - and I found it surprisingly useful

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Like many people, I exchange frequent text messages with family, relatives, friends, and other individuals in my life. But I don't necessarily pause to understand how I'm communicating with them. Now I can ask ChatGPT for some armchair analysis based on those messages.

On Thursday, OpenAI rolled out a new plugin for ChatGPT that connects to your Apple iMessages, but only on the Mac. With this new skill, you can ask ChatGPT to send a text to someone on your behalf. OK, that's not a big deal, as you can simply use the Messages app to send the text yourself. You can also tell the AI to find and summarize specific texts based on name, topic, and other criteria. OK, that sounds useful.

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(Disclosure: Ziff Davis, ZDNET's parent company, filed an April 2025 lawsuit against OpenAI, alleging it infringed Ziff Davis copyrights in training and operating its AI systems.)

But the coolest part is asking ChatGPT to analyze your messages, either in general or with a specific person. In response, the AI suggests ways to communicate more effectively.

To get started on your Mac, make sure you've updated ChatGPT to the latest version. In the app, click the ChatGPT menu at the top, select "Check for Update," and then allow the latest one to download and install.

Next, click your account name at the bottom of the left pane and select Settings. At the Settings screen, look for the Integrations section and select Plugins. Click the Browse directory button, then start typing the word "Messages." Apple's Messages should appear among the results. Click the Install button next to its entry to add it.

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Ah, but there's more. You'll next be asked to grant ChatGPT the necessary permissions on your Mac to access your text messages. Yes, there are some privacy implications, as the AI needs to read your texts to deliver its results. If you're OK with this, then allow those permissions, and you're set.

As the first step, you might want to simply compose and send a text message to someone. At the prompt, type "Send the following message to [name of person] using @." After you type the @, start typing the word Messages and then choose Apple Messages from the list of plugins. Type the message you wish to send and submit the prompt.