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Issue No. 4 · Tuesday, August 25, 2026 · By Scott Olsen

PULL UP A CHAIR

Back in my day (I've always wanted to say that), campaign season meant yard signs and robocalls. This year, two AI companies wrote checks to fight each other over how AI should be regulated, and somehow landed on backing the same guy, Byron Donalds, for governor.

I've been watching this race the way you watch a fender bender in slow motion. Can't look away.

Here's the setup. "Leading the Future" wants light AI regulation, backed by well-known Silicon Valley venture capitalist Marc Andreessen and OpenAI's president, Greg Brockman. "Public First Action" wants stricter oversight, backed by Anthropic's CEO, Dario Amodei. These two just spent a combined $23 million fighting each other in a New York primary. In Florida, both wrote checks north of $2 million for Donalds. Same race, same candidate, opposite sides of the fight. Somebody explain to me how that's not just buying a seat at the table, because that's what it looks like from here.

Then the data centers. A UNF poll found 68% of Florida voters don't want one built anywhere near them, and it's turned into one of the biggest fights of the whole governor's race. I spent eleven years explaining server rooms to people who thought "the cloud" was, you know, a cloud. Now half the state has opinions about substations and water cooling. Didn't see that coming.

And the part that's less funny. The National Republican Senatorial Committee ran an AI-generated video of Texas Senate candidate James Talarico "reading" his old tweets. It's labeled AI-generated, technically. Critics say the label's the size of a postage stamp. Judge for yourself, but I know what I'd call an ad designed so you almost miss the fine print.

No neat bow on this one. Just a weird year to be paying attention. If your office touches elections, planning, or utilities, some version of this is probably already sitting in your inbox. Reply and tell me how it's actually showing up on your desk, not just in the headlines.

THIS WEEK'S PICK

The AI already inside Microsoft 365 you are not using

If your office already pays for Microsoft 365, you already have some real AI, no purchase order needed. The catch is that "Copilot" is actually the name of three different things, and knowing which one you have changes what it can actually do for you.

START HERE  WHAT YOU ALREADY HAVE, FREE

Copilot Chat

Any paid Microsoft 365 Business or Government tier already includes Copilot Chat at no extra cost, including Business Basic, the cheapest one. Sign in at m365.cloud.microsoft/chat with your work account, or use the Copilot app, and you can draft, summarize, brainstorm, and generate images right now. The limit: this version only knows what is public on the internet plus whatever you type or paste in. It cannot see your office's own email, files, or SharePoint. Think of it as a very capable outside consultant who has never seen your case files.

Cost: included with any paid M365 tier     Setup: sign in with your work account, nothing to install

IF YOU WANT IT TO READ YOUR OWN FILES

The paid Microsoft 365 Copilot add-on

This is the version that can actually read your own inbox, your files in SharePoint or OneDrive, and your Teams chats, and it is what powers full Copilot inside Word, Excel, PowerPoint, Outlook, and Teams, drafting from your real documents, not just general knowledge. It is a separate purchase on top of your existing license, currently listed around $21 per user per month for smaller organizations, sometimes discounted, and it cannot be bought standalone, you need an eligible Microsoft 365 plan first. Pricing has moved twice already this year, so confirm the current number with your Microsoft partner before you budget for it.

Cost: roughly $18 to $21/user/month, on top of your base license     Setup: ask your Microsoft partner or reseller to add it

IF YOU RUN GOVERNMENT CLOUD (GCC)

Same free tier, some extra steps for the paid one

The free Copilot Chat is included in GCC the same as commercially. One real difference: web search inside Copilot defaults to off in GCC, not just GCC-High, an admin has to explicitly turn it on, so a first try can look weaker than the commercial version until that setting is flipped. The paid add-on reached GCC-High only in December 2025, so if your office is specifically on GCC-High, check current availability with your Microsoft partner before assuming it is purchasable. And do not assume your office is on GCC at all just because you work in government: it is generally required for offices touching CJIS data, court records, or certain federal compliance requirements, but general clerk, finance, or HR functions without that exposure often run standard commercial Microsoft 365. Check with whoever manages your license if you are not sure which one you have.

HOW TO ACTUALLY USE IT

1.  Sign in at m365.cloud.microsoft/chat with your work account and ask it to draft something you would normally write from scratch, a meeting notice, a form letter, a policy summary.

2.  In Outlook, use Copilot to summarize a long thread you have been putting off, look for Summarize when Copilot Chat is pinned to your navigation bar. Note the difference: drafting a full reply through the ribbon's Copilot button is part of the paid add-on above, not this free tier, so do not expect that specific button to work yet.

3.  Try the free image generation and "Copilot Pages" to put together a flyer or public notice without opening design software you do not have.

The honest catch: the Copilot icon shows up in Word, Excel, and Outlook for everyone, licensed for the paid version or not. Clicking it does not mean you have the paid add-on, or that it can see anything inside your own files. Unless your office specifically bought the add-on, assume it only knows what is public on the internet plus whatever you paste in, nothing from your case files, budgets, or minutes.

THE RULEBOOK · TWO RULES WORTH A GLANCE

What changed that affects how your office can use AI. Short, plain, and sourced. The part that keeps you out of the newspaper. Tagged Local for a city or county action, State for a change at the state level, Federal for a change at the federal level that reaches your desk.

Local

A small Idaho city wrote an AI policy worth copying

Hayden, Idaho, a city of about 17,000, has a resolution on today's council agenda to add a formal AI use policy to its employee manual. As proposed, it requires staff to disclose when AI helped create or alter something, verify any AI-generated fact against at least one reliable outside source before it goes into city records, complete basic training on not feeding private information into AI tools, and treat AI as something that assists a decision, never replaces the judgment behind it. The vote is happening the same day this issue goes out, so treat this as pending, not yet adopted, as of send time.

What it means for you: this is a genuinely small-office-sized policy, four plain rules, not a forty-page framework. If your office does not have a written AI policy yet, this is a usable starting template regardless of how the Hayden vote lands.

Source: City of Hayden, ID council agenda (August 2026) →

State

California moves closer to requiring a 45-day heads-up before your office rolls out AI

AB 2656 would require any California state or local public employer to give the union representing affected employees 45 days' written notice before rolling out generative AI that touches a union job's duties. It cleared the Senate Appropriations Committee 7-0 on August 13 and is now positioned for a full Senate floor vote before the legislature adjourns August 31.

What it means for you: even outside California, this is worth watching as a model. Before you flip on an AI tool for a unionized department anywhere, check your own state's public-sector labor rules first, a quiet rollout can turn into a labor dispute faster than you would expect.

Source: California Legislative Information, AB 2656 (August 2026) →

FREE THIS WEEK

A free AI Use Policy Template for your office

The Rulebook keeps flagging new AI rules landing on local offices. Here is a running start: a plain-language AI Acceptable Use Policy, built for local government, that you can fill in and adopt. It is a Google Doc, so you click, make your own copy, and edit away. Nothing to buy.

Get the free template

ONE MORE QUICK WIN

The Copilot icon is not proof of what you are licensed for

Before you tell your team "we have AI now," check your actual license, not just what shows up in the ribbon. Ten minutes with whoever manages your Microsoft account settles it, and saves you from either underusing something you already pay for or assuming you have something you do not.

Know someone at another city or county who could use this? Forward it over.

Subscribe free

Until next week,

Scott Olsen, CGCIO

Former CIO with eleven years in Florida local government

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Practical guidance for local government, not legal or procurement advice.

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