I’m in the process of updating some of our internal shortcuts to use OpenAI’s API-only GPT-4.1 model instead of Claude, and in doing that, I realized that it was a good opportunity to finally learn the new Responses API. Announced by OpenAI a couple months back, the Responses API will eventually replace the old Chat...
Sycophancy in GPT-4o→
OpenAI found itself in the middle of another controversy earlier this week, only this time it wasn’t about publishers or regulation, but about its core product – ChatGPT. Specifically, after rolling out an update to the default 4o model with improved personality, users started noticing that ChatGPT was adopting highly sycophantic behavior: it weirdly agreed with users on all kinds of prompts, even about topics that would typically warrant some justified pushback from a digital assistant. (Simon Willison and Ethan Mollick have a good roundup of the examples as well as the change in the system prompt that may have caused this.) OpenAI had to roll back the update and explain what happened on the company’s blog:
We have rolled back last week’s GPT‑4o update in ChatGPT so people are now using an earlier version with more balanced behavior. The update we removed was overly flattering or agreeable—often described as sycophantic.
We are actively testing new fixes to address the issue. We’re revising how we collect and incorporate feedback to heavily weight long-term user satisfaction and we’re introducing more personalization features, giving users greater control over how ChatGPT behaves.
And:
We also believe users should have more control over how ChatGPT behaves and, to the extent that it is safe and feasible, make adjustments if they don’t agree with the default behavior.
Today, users can give the model specific instructions to shape its behavior with features like custom instructions. We’re also building new, easier ways for users to do this. For example, users will be able to give real-time feedback to directly influence their interactions and choose from multiple default personalities.
“Easier ways” for users to adjust ChatGPT’s behavior sound to me like a user-friendly toggle or slider to adjust ChatGPT’s personality (Grok has something similar, albeit unhinged), which I think would be a reasonable addition to the product. I’ve long argued that Siri should come with an adjustable personality similar to CARROT Weather, which lets you tweak whether you want the app to be “evil” or “professional” with a slider. I increasingly feel like that sort of option would make a lot of sense for modern LLMs, too.
Tackling Trackers
This week, Federico and John tackle tracking apps. From database apps to media trackers, they consider what makes a good tracking app no matter what you’re tracking.
On AppStories+, Federico quizzes John about what’s on his desk, the tech he’d be happy to have a burgler steal, and more.
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What Siri Isn’t: Perplexity’s Voice Assistant and the Potential of LLMs Integrated with iOS
You’ve probably heard that Perplexity – a company whose web scraping tactics I generally despise, and the only AI bot we still block at MacStories – has rolled out an iOS version of their voice assistant that integrates with several native features of the operating system. Here’s their promo video in case you missed it:
This is a very clever idea: while other major LLMs’ voice modes are limited to having a conversation with the chatbot (with the kind of quality and conversation flow that, frankly, annihilates Siri), Perplexity put a different spin on it: they used native Apple APIs and frameworks to make conversations more actionable (some may even say “agentic”) and integrated with the Apple apps you use every day. I’ve seen a lot of people calling Perplexity’s voice assistant “what Siri should be” or arguing that Apple should consider Perplexity as an acquisition target because of this, and I thought I’d share some additional comments and notes after having played with their voice mode for a while.
The Current State of Major LLMs and Their Shortcuts Integrations
Earlier this week, I decided to do some research about the current state of major LLM apps and their implementations of Shortcuts actions. While millions of people are interacting with chatbots on a daily basis using their respective websites and dedicated mobile apps, I thought it’d be interesting to see how these popular services are...
How We’re Using AI
This week, Federico and John revisit the fast-paced world of artificial intelligence to describe how they’re using a variety of tools for their everyday workflows.
On AppStories+, John shares his theory of the way we’ll look at AI models in the future.
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Automation Academy: How I Turn Voice Recordings into Searchable Obsidian Notes with Shortcuts, Hazel, and LLMs
As I mentioned last week in the MacStories Weekly newsletter and have been hinting recently on both Connected and AppStories, I’m in the process of building a “perfect memory” system in Obsidian that allows me to save, archive, and search anything I write, think about, or come across on the Internet. This project is a...
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Time for Calendars
This week, Federico and John survey their favorite calendar apps, discussing the strengths and weaknesses of each.
On AppStories+, Federico shares Shortcuts tips for working with Google’s Gemini API and the highly structured data it returns. Plus he and John share their concern and cautious optimism for the future of Shortcuts.
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My Obsidian Setup, Part 12: Rethinking YouTube Watch Later with Markdown and AI
Earlier this week on the Connected Pro pre-show, I mentioned that I’ve decided to take on the challenge of building a “perfect memory” for myself in Obsidian. The project involves three key aspects: Saving all kinds of content into Obsidian: my articles, transcribed voice recordings, but also videos I watch online and interesting webpages I...

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