ChatGPT (OpenAI)

ChatGPT is OpenAI's assistant at chatgpt.com. For most shluchim it is still the first AI they try, and in July 2026 the group admin went back to recommending ChatGPT Plus for beginners ("ChatGPT has caught up majorly"), mainly because it makes flyers and pictures and Claude does not.

The product changed shape in 2026. It is now three tabs in one app:

• Chat is the normal conversation.
• Work is an agent mode (launched July 2026) that goes off and returns finished files: a document, a spreadsheet, a deck, a website.
• Codex is OpenAI's coding agent, folded into the ChatGPT desktop app. Work runs on the same engine and shares Codex's usage allowance.

A member's short version, from October 2026: Chat to brainstorm, Work to create, a Dot to keep watch.

Plans and prices (checked October 2026)

Plan	Price (US)	What it adds
Free	$0	Unlimited everyday text chat on GPT-6 Luna; limited uploads, images, voice, deep research, Work and Codex
Go	$8/month	More messages, uploads and images; longer memory. May show ads
Plus	$20/month	GPT-6 Sol in Chat, GPT-6 Astra and GPT-6.1 Sol in Work and Codex, Projects, scheduled tasks, custom GPTs, Sites
Pro	$100, $200 or $500/month	Much higher usage, GPT-6 Pro in Chat, one Dot included. Only Pro 500 has Ultrafast mode
Business	$25/seat monthly or $20/seat annually (Standard); $125 or $100 (Premium)	Shared workspace, admin controls. Minimum 2 seats. Dots need Premium seats
Enterprise	Contact sales

Prices outside the US vary. Go launched worldwide on January 16, 2026. The three Pro tiers date from September 29, 2026; before that Pro was a single $200 plan.

Free programs worth knowing:

• ChatGPT for Teachers is free for verified US K-12 educators through June 2028 (chatgpt.com/plans/k12-teachers). Check the eligibility rules before a Hebrew school teacher applies.
• OpenAI for Nonprofits gives up to 75% off ChatGPT Business or Enterprise, with verification through Goodstack (help.openai.com, OpenAI for Nonprofits). See the next section for how it has gone for Chabad Houses.

The nonprofit discount in practice

Several members went through this in mid-2026. What they reported (July to September 2026, not OpenAI's wording):

• Approval comes from Goodstack, and it can take a while. One shliach was approved even though an older version of the page excluded religious organizations.
• After approval, the pricing page still shows full price. Switch to a Business plan, choose at least 2 seats, and the discount appears only at checkout.
• Members paid roughly $8 to $10 per seat per month after the discount. A shliach in Europe could not tell from his invoice whether it applied.
• Moving from Plus or Pro to Business creates a new workspace. ChatGPT offers to move chats and custom GPTs across; memory may not come with them.
• The discount covers seats, not extra Codex or Work usage bought on top.

See Nonprofit Discounts for the Claude and Google equivalents.

Current models

OpenAI renames and replaces models often. As of October 21, 2026:

• GPT-6 Astra (September 3, 2026) is OpenAI's top model. On Plus it runs only inside Work and Codex; Pro and Business get it in Chat as GPT-6 Pro.
• GPT-6.1 Sol (September 29, 2026, announced at DevDay) comes close to Astra at a lower cost. Plus users get it in Work and Codex.
• GPT-6 Sol powers everyday Chat on paid plans; GPT-6 Luna powers Chat on Free and Go (October 7, 2026).
• The GPT-5.6 family (Sol, Terra, Luna, July 2026) is still listed for paid plans. GPT-5.5 left ChatGPT, Work and Codex on October 14, 2026.

A tip the group found useful in September 2026 when Plus usage ran out mid-week: switch big jobs to a lighter model (Luna) or a lower thinking setting, and save Work mode for the largest tasks. Put a line in your custom instructions asking ChatGPT to say when a cheaper setting would do.

What changed in 2026

• Intelligent UI (October 7). Answers can now come back as interactive pieces: charts, tappable buttons, forms, side-by-side comparisons, small tools. This rolled out to every plan in the Chat tab.
• Dots (September 29). Always-on agents, each with its own cloud computer and browser, connected to over 4,000 apps through plugins, reachable from ChatGPT, Slack or Teams, or by voice call. Dots run on GPT-6 Astra. They are available on Pro, Business Premium and Enterprise, in eligible countries only. The group admin uses one; in October a member's verdict was "fine for research and drafting, not for donor or family data." See Personal AI Agents and Agent Safety.
• ChatGPT Images 2.5 (September 8). Sharper images, faster generation, better edits across several turns, and a Sketch feature to draw what you want. Available on all plans. Members found it good for flyers and a 10-page children's comic with consistent characters, but warned that it redraws faces in a collage instead of pasting the real photo, and that it lowers the resolution of large images. Use Canva for collages of real photos.
• ChatGPT for Teens (August 18). Anyone ChatGPT estimates is under 18, or who says they are 13 to 17, is placed in a teen version with Study Mode, homework reminders that steer toward working it out, and parental controls such as Quiet Hours. Useful to know for a CTeen program or a teen in your own home.
• Sites. Ask ChatGPT (in Work or Codex) to build a website and it hosts it for you. Plus, Pro and Business only. A shliach built a dedications microsite this way in October; another built a community calendar hub and embedded it in a ChabadOne page.
• Office add-ins. ChatGPT now works inside Word, Excel, PowerPoint and Google Sheets. Limited on Free and Go, full on Plus and up.
• Audio uploads (October 6). Paid plans can now upload an audio file and get a transcript, summary or answers. Earlier in 2026 a member could not get a 40-minute recording transcribed at all, so this is new. For Hebrew and Yiddish, see Transcription.
• Memory "dreaming" (June 4). A rebuilt memory system that keeps what ChatGPT remembers about you fresher. Meant to fix the complaint that ChatGPT forgets standing instructions.
• Sora is gone. OpenAI shut the Sora video app in spring 2026. See Sora and Video Creation.

What shluchim use it for

• Flyers and pictures. The reason it is the beginner pick. Put the Flyer Designer prompt in a Project's Instructions box, not in its Sources (members found it then treats the prompt as a file to quote). "Thinking mode usually does better than Pro" for flyers, one member found. The Canva plugin can turn a ChatGPT flyer into an editable Canva file. See Flyer Design.
• Letters and emails. See Letter Writing.
• Email triage. One shliach connected ChatGPT to his mailbox: every hour it drafts replies, in his style, to tourists asking about kosher food and minyan times, then notifies him to edit and send.
• Shiur follow-up. A rabbi uploaded the phone recording of a 50-minute shiur and got three discussion questions for his class WhatsApp group.
• Routes and lists. A member uploaded 45 volunteers and 600 deliveries and got a plan that "did an absolutely amazing job."
• Websites. Members built a full site with Work in October 2026; for anything bigger than a page, Work itself suggested moving to Codex.
• Reading aloud. Members find ChatGPT's read-aloud more conversational than Claude's for listening to a document in the car.

What to watch out for

• Usage runs out. "You're out of Codex and Work usage" is a common message on Plus. Work and Codex share one allowance, separate from Chat.
• Recent events. In December 2025 ChatGPT denied a real news event until shown a link. Give it links for anything recent.
• Thinking mode matters. Members saw accuracy "shoot up tremendously" when they switched to a thinking model. On Free you get less of it.
• It flatters. Ask for honest feedback in so many words. See Letter Writing.
• Torah citations. It still invents sources. See AI and Torah Accuracy.
• Work on the phone. Through October 2026, Work sessions started on a computer did not show in the phone app.
• Money connections. ChatGPT can now link to bank accounts for personal finance reports. A member asked in August whether connecting an organization's bank account is wise; nobody had a good answer. Start with read-only access, if at all. See Privacy & Data.
• Billing support is slow. A member waited two days per reply in October 2026.

Phone access

The 1-800-CHATGPT line still works from any phone, including a basic phone with no internet: about 30 free minutes a month, US and Canada only. A member found it hung up mid-sentence. The WhatsApp version stopped working outside Europe after January 15, 2026, when Meta changed its rules for AI bots on WhatsApp.

Moving between ChatGPT and other tools

• To a new ChatGPT account: open Settings, then Personalization, then Memory, copy the list, and paste it into the new account with "Add this to memory."
• To Claude: ask Claude for a prompt that makes ChatGPT write out everything it knows about you, then export your chat history and upload it so Claude can search it.

Related

• Claude, the other main assistant in the group.
• Gemini, for Google Workspace.
• Model Leapfrog, why the "best" model keeps changing.
• Personal AI Agents, where Dots fits next to other always-on agents.
• Paid vs Free
• Toolbox