Every month brings a flood of AI announcements. Most don’t matter to a small business. This roundup picks out the handful that do, explains them in plain English, and tells you what, if anything, to do about them. Here’s what mattered in September 2026.
This month in 60 seconds
- Action needed: OpenAI is retiring custom GPTs on December 11, 2026. If your business relies on one, plan its migration now.
- Microsoft 365 Copilot can now take on multi-step work with your approval, and manage your Outlook inbox in plain English.
- Google Gemini now connects to more business apps and has a desktop app for Windows.
- New AI models from OpenAI and Google are rolling out. Useful, but no reason to switch tools mid-project.
- A reminder from a major outage: have a backup plan for AI-dependent work.
1. OpenAI is retiring custom GPTs (deadline: December 11)
OpenAI announced that custom GPTs, the tailored ChatGPT assistants many businesses built for things like answering policy questions or drafting proposals in a house style, will stop running on December 11, 2026. The change affects all ChatGPT plans. They’re being replaced by plugins and “skills,” and OpenAI offers a migration tool that carries over a GPT’s instructions and knowledge files. Some things don’t carry over automatically, including custom actions, the selected model, past conversations and some sharing settings. Some Enterprise workspaces may qualify for a deferral.
What to do now
Our take: This is a good moment to ask whether each GPT is still earning its keep. If one mainly answers questions from your documents for customers, a purpose-built tool like the one in our CustomGPT.ai guide may be a better long-term home.
2. Microsoft 365 Copilot takes on bigger jobs
Microsoft’s September release notes include several features that matter for small teams on Microsoft 365:
- Copilot Cowork: describe an outcome, such as “prepare a summary of this client’s open issues and draft a follow-up,” and Copilot gathers context from your email, meetings, chats and files, then completes the steps with your approval.
- Inbox triage in plain English: ask Copilot in Outlook to “move emails from Contoso about invoices to my Finance folder” or clean up newsletters. It asks for confirmation before acting on more than five emails or changing inbox rules.
- Find meetings by topic: Copilot can now search meeting invitations, chats and transcripts from the past two months.
- Planner agent: ask “what’s due this week?” and manage tasks in natural language.
Our take: Agent features like Cowork are where the real time savings are heading, but they act on your real email and files. Start with low-stakes tasks, and make sure your AI policy covers what Copilot may do on someone’s behalf. Availability depends on your license and is rolling out in phases.
3. Google Gemini connects to more of your tools
Google added Connected Apps to the Gemini app, linking it to third-party tools including Airtable, monday.com, PandaDoc, Squarespace and Webflow. It also launched a Gemini app for Windows (opened with Alt + Space) that can work across your Gmail and Drive files, and brought its improved voice models into Google Workspace, so you can get things done by voice in Gmail, Docs and Keep.
Our take: If you’re on Google Workspace, Gemini is increasingly a hub for your other business apps. As with any integration, connect only the apps you need, and review what each connection can access.
4. New AI models: useful, but don’t chase them
OpenAI began rolling out its next generation of GPT models, and Google released Gemini 3.8 Flash, with gains in multi-step problem solving, plus a limited early release of its most capable model, Gemini 4. New models typically arrive in your existing tools automatically over the following weeks.
Our take: For most small businesses, the model matters less than how well a tool fits your workflow and protects your data. If something you rely on starts behaving differently after an update, re-test your key prompts. Not sure which assistant fits? See our assistant comparison or the AI tool finder.
5. A reminder: have a plan B
A widely reported outage on September 3 disrupted several major AI assistants on the same day. Outages are rare, but if AI is now part of how you answer customers or meet deadlines, decide in advance what happens when it’s down: a backup tool, saved templates, or simply doing the task by hand.
On the regulatory radar
Colorado: the state’s replacement AI law (SB 26-189) takes effect January 1, 2027. If you use AI to help make consequential decisions about people, such as hiring, lending, housing or insurance, you’ll need to notify them, name a trained person who can override AI decisions, and explain adverse outcomes. EU: if you sell into Europe, rules for marking AI-generated content are being phased in, with some deadlines extended to December 2026. See our full guide: AI regulations for businesses in 2026.
