Jun 2, 2026
The ho-hum that is coming, the one already arriving at the edges, is something different. It is not the slowing of capability. It is the migration of AI from topic to infrastructure. It will go into the background. From the thing you think about to the thing that makes everything else work. Consider when the iPhone 18 marries Gemini into its operating system. (Of course, knowing Apple they will bungle it up.)
[AI models are having their iPhone moment. What’s Next?
But it’s actually worse than that because even subscribing to Office 365 doesn’t fix the problem. You need a newer version of Office, which necessitates a newer version of macOS, which may necessitate getting a new Mac—all to fix what seems like an artificial problem.
Michael Tsai - Blog - Bricking Microsoft Office 2019
Harder and harder to keep your hardware and software going and secure.
The old plan wasn’t bad, but it also wasn’t the best plan that could be made with the information available. I debated what to do with it. Then I thought about me three months from now, and asked myself – do I want to regret not making this change then?
Making a New Plan | Accidentally in Code
This is such a common challenge in leadership.
Do you demonstrate consistency and with that help give others confidence in their ability to act?
Or.
Do you change as you get new information and so stay on the edge of what’s possible?
These users — much like the users of effectively every subsidized AI subscription — never really knew how much anything they did cost, because Microsoft intentionally hid the actual cost of prompts and allowed users to spend obscene amounts as a way of boosting growth for GitHub Copilot.
This problem is industry-wide.
Every single user of every single AI subscription service is having their tokens subsidized and the actual cost of AI obfuscated. As a result, every frothy, fluffy hype-piece about Claude Code or AI in general is a kalopsia — the belief that something is more beautiful than it really is.
This. This is what I worry about on behalf of nonprofits and the systems the may be setting up on these subsidized (and for them further discounted) accounts.
In the study, Nvidia and Microsoft outlined three distinct kinds of blind goal-directed (BGD) activity it often saw in AI agents. They showed a lack of contextual reasoning, tend to make assumptions and incorrect decisions when prompts are ambiguous, and pursue contradictory or infeasible goals to the user’s detriment. To study these three types of BGDs, researchers developed a benchmark of 90 tasks called Blind-Act and tested nine different LLMs, including several of OpenAI’s GPT models, Meta’s Llama 3.2, and two of Anthropic’s Claude models.
[Nvidia and Microsoft Researchers Say AI Agents Don
May 29, 2026
Coding agents really did change everything. These are tools which burn vastly more tokens, but are also quickly becoming daily drivers for the work carried out by extremely well-compensated professionals. Right now that’s still mostly software engineers, but a coding agent is a tool that can automate anything you can do by typing commands into a computer… so they are clearly applicable to a much wider set of skilled knowledge workers.
I think Anthropic and OpenAI have found product-market fit
This is what I’m finding. I’m using them to structure skills files which then interact with python scripts to things I need done. I’m not a coder. But I’m using these agents in the same model.
May 28, 2026
The lapse comes as the Department of Justice’s Office on Violence Against Women withholds $150 million in taxpayer dollars meant to be distributed in fiscal 2025 to help survivors of domestic violence, sexual assault, stalking and trafficking.
The 19th reached out to over 250 organizations and municipalities that had previously received funding from the Office on Violence Against Women to ask how the delay in fiscal 2025 funds and the stalling of fiscal 2026 grant applications has impacted them. The 48 that responded shared stories of layoffs, diminished services for survivors and sacrifices among advocates, who have taken voluntary pay cuts to make sure survivors get the life-saving support they need.
How a missing $150 million is impacting domestic violence services
These organizations are already chronically underfunded.
May 27, 2026
The API features an MCP and a CLI and ultimately opens the door to more members from our community building tools and apps on top of Buffer. Opening up Buffer has a huge potential impact for our customers and community members, and we couldn’t be more excited to see what you build.
Buffer’s API is Open for Building
Opportunity here to build shared tools for civil society orgs using Buffer.
May 26, 2026
It is the procurement model. Companies that signed up for a productivity tool are discovering they signed up for a metered utility, and the meter runs when nobody is looking. The fix may be straightforward: capped budgets per engineer, tiered access for high-leverage roles, agent runtime quotas.
Many of the larger buyers are already there. But the implication is that the era of “give every employee a Claude Code seat” is closing, and what replaces it will look more like AWS billing than like Office licences.
Microsoft’s quiet Claude Code retreat and the real cost of enterprise AI
Important for nonprofits (a) to budget; (b) to develop sector resources.
That is why, if we want this technology to go well, it is enormously important that there be people outside those incentives—people who care about things going well and insist on safety, who are paying close attention, who are willing to say hard things, who are willing to be our earnest, thoughtful, critics. It is through dialogue and mutual effort, through the push and pull, that humanity will achieve great things.
Anthropic co-founder Chris Olah’s remarks on Pope Leo XIV.
Sounds like a civil society call to action to me.
Former officials and industry leaders fear the Cybersecurity and Infrastructure Security Agency no longer has the capacity to help utilities, banks and other critical infrastructure operators prepare for a coming wave of AI-fueled cyberattacks.
CISA takes backseat in White House AI cyber response
I just read AI Agent Traps which has given me a more expansive reference for a set of cyber risks.
Now, it’s true that some workers don’t have to be forced to use AI. Workers who enjoy a high degree of autonomy (that is to say, workers who are positioned to ignore workplace coercion) can adopt AI in ways that they feel suited to, just as those early web users and Visicalc smugglers did. They can fulfill the maxim that labor-driven automation improves quality, while resisting capital’s insistence that automation be used to increase throughput at quality’s expense.
They can act as centaurs (workers assisted by technology), not as reverse-centaurs (workers who are recruited to serve as peripherals for machines). As with all technology questions, what the technology does is nowhere near as important as who the tech does it for and who the tech does it to…
[Pluralistic: The AI bubble isn’t like the internet bubble (26 May 2026)
May 24, 2026
On making my own tools: a Readwise-to-PDF Archiver
I’ve been spending time lately refining my knowledge management system. I want to be sure I’m archiving permanent PDFs of the material that is really key to the projects I’m working on—not just the stuff I save to Readwise, but the articles I actually take the time to annotate and think through.
To make that easier, I used Gemini CLI to help me build a little archiver utility. I’ve shared it on GitHub here: Readwise_PDFArchiver_Public.
This is the third workflow utility I’ve created for myself now. Each time I do this, it gets a bit easier. I’m learning how to ask for things more efficiently, I know to clarify the architecture at the beginning, and I’m getting better at working through the technical hurdles that come up.
It’s interesting to look at these three small utilities—two of them don’t use AI at all in the final code; I just used AI to write them. The other one does use it for some analysis. What AI has really opened up for me is the option to use Python for these routine tasks that just make the maintenance of my digital systems work better.
It’s about building a bespoke workflow. The trick is keeping it only on the things that are just mine, like my PKMS. Versus workflows that are shared or nested in a broader collaboration. All of it has me thinking about how I improve my own computing environment and how we have a solid set of organizational Standard Operating Procedures so that we can be orchestrated in our team-wide or organization-wide efforts.
May 23, 2026
But what if the key to serving your users best depends in large part upon training a machine learning algorithm? What if that ML algorithm needs a massive training dataset? In an age when machine learning is in its ascendancy, this is increasingly a critical design objective.
Seeing Like an Algorithm | Remains of the Day
This an older article — and long! — but if you do any kind of modeling to better understand the preferences of your users, it is well worth the read.
May 21, 2026
[Switching vendors] also applies to other layers of the tech stack (database, etc.) to various extents as well as to some other types of software, e.g. it’s trivial to export your bookmarks from one bookmark manager to another if they both have APIs or import/export capabilities — or, with a bit more effort, you can write your own.
What If Lock-In Doesn’t Matter So Much Anymore?
Another for the “how do we bring more portability and agency to the nonprofit tech stack” file. Those are also the things that bring negotiating power.
This is a literal revolution but one against the participatory web, against us: The goal is to take away the web and guide people into Google’s abstraction on top of it. An abstraction they control and moderate. It’s about monopolizing access to information. A true Metaverse unbound by open standards and your ability to build your own corner of the web according to your needs and desires. Which – given how strong Google’s influence is on web standards – will change the shape of the standards for the technological landscape we are building the web on.
On Google declaring war on the Web
Let’s be frank: we haven’t been paying attention to context for a long time. That’s what hurts long simmering news stories, fuels mis/disinformation, dampens civic engagement.
So the question is how do we use these tools, how do we reshape them, what are we advocating for?
A demand co-op is a cooperative that pools and directs the spending power of its members. Demand determines what gets built, who survives, and where wealth flows. Most communities already have enormous spending power, but because that demand is unorganized, the value created from it is captured by outside businesses and investors. A demand co-op coordinates that spending so economic activity can build communal businesses, assets, and long-term ownership instead of constant leakage.
This reminds me of open source bounties. I’ve been thinking a lot about to aggregate the small nonprofits served by TechSoup turn philanthropy into negotiating power. Group buying, mutualism, are all a part of the answer. I will add this to the list.
The choice reflects a broader Google strategy: Stay at the frontier, but also prioritize models cheap and fast enough to deploy across products used by billions, rather than chasing benchmark supremacy alone.
How Google plans to win the AI war
What impact does this have on the environmental impact?
If they wanted an AI essay, they would have asked ChatGPT themselves. They asked you because they wanted your human judgment.
Please.