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OpenAI now saves deleted chats?!
Plus: How to design a workflow that works while you sleep

Welcome, Automaters!
Here's what we have for you today
🤫 OpenAI’s Privacy Promise Took a Hit

Guess what?
Your deleted ChatGPT chats — you know, those ones you thought were gone for good — might not be so “deleted” anymore.
We’ve been tracking the situation since it dropped late Thursday, and yep — it only got messier over the weekend.
So let’s break it down real quick:
Late Thursday, OpenAI dropped a bombshell: it’s being forced to keep all user chats — even the deleted ones all because of a court order tied to a lawsuit from The New York Times.
What’s this all about?
Apparently, the NYT suspects that some users may have prompted ChatGPT to recreate paywalled articles (👀). But since OpenAI doesn’t store deleted chats by default, the judge granted an order requiring them to retain all chats indefinitely — deleted or not.
So yeah… that “oops, I shouldn’t have asked that” convo? Is probably still there. 🫠
OpenAI, for their part, aren’t too happy.
In fact, they’re calling major BS.
They’ve slammed the order as a “speculative fishing expedition”, that forces them to break long-standing privacy norms based on what-if evidence that might not even exist.
But unless the court changes its mind, OpenAI’s hands are tied.
And that means:
If you use ChatGPT Free, Plus, Pro, or OpenAI’s API — this applies to you.
If you’re on ChatGPT Enterprise, Edu, or have a Zero Data Retention agreement — you’re off the hook.
As for your deleted chats, OpenAI explains that:
Your data isn’t just floating around — it’s locked away in a separate, locked-down system under a legal hold.
Only a tiny, audited legal and security team can access it.
And nope, it’s not automatically getting shared with The New York Times or anyone else.
Still, let’s be real — it’s a weird vibe knowing your “deleted” chats are technically on legal life support—-especially for a company that’s built a lot of user trust around privacy.
So, OpenAI has:
Appealed the order
Requested oral arguments, hoping user testimony might help change the outcome
And is basically trying to convince the court that this is too much and breaks user trust
Also? They're stressing a lot about the EU’s “Right to Be Forgotten” law — because keeping deleted chats might totally clash with GDPR. So this whole thing could spiral into a major international data drama.
Bottom line?
If you’ve used ChatGPT in the past few months and deleted a spicy convo or two...There’s a small chance it’s now chilling in a legal vault somewhere. 🫣
And honestly, if you’re thinking of switching tools because of this, you’re not alone — some users are already eyeing alternatives.
But if you choose to stay, maybe hold off on telling ChatGPT your deepest secrets for now. And seriously — for the love of writers’ rights — don’t ask ChatGPT to rewrite the entire NYT homepage.
Just saying. 😅
We’ll keep watching this story as it unfolds, and keep you updated every step of the way, but for now you can catch the full details here.
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🧑⚖️ The Legal World’s New Rule

The High Court in England just threw some serious shade at lawyers who rely way too much on AI tools like ChatGPT for legal research.
Why?
Because AI might sound super confident, but it’s basically that one friend who talks big and totally messes up facts like, big time.
So, in short, the court made it crystal clear:
Lawyers have a professional duty to fact-check AI outputs using real, reliable sources before bringing that mess to court.
And in case you haven’t heard, this fuss didn’t just pop out of nowhere — two lawyers actually got caught slipping:
One filed court papers with 45 citations, but here’s the plot twist — 18 of those cases were straight-up fake. As in, “did-not-exist” fake, while many others “did not contain the quotations that were attributed to them, did not support the propositions for which they were cited, and did not have any relevance to the subject matter of the application.”
Another lawyer cited five cases that likely came from AI-generated summaries she found through Google or Safari. She denied using AI directly, but the court wasn’t buying the “accidental” excuse.
In light of all this, Judge Victoria Sharp made it clear that ignoring your duty to verify citations isn’t just sloppy — it’s serious. And the consequences can range from:
Public scolding (ouch),
Paying costs,
Contempt of court proceedings,
To even police involvement. Yeah, it can get that wild.
The big takeaway? AI is cool — but if you’re a lawyer, don’t let it do your homework solo. Either check your facts or risk some serious legal karma, because in law, “plausible-sounding” just ain’t good enough.
So, what do you think? should lawyers get AI fact-checkers on speed dial, or stick to the old-school grind?
Either way, this ruling is a solid reminder that AI isn’t the “plug and play” magic wand we all want it to be—at least, not yet.
🔧 AI Troubleshooter: When ChatGPT Only Reads Half Your File
Hey friends — let’s talk about one of those low-key frustrating moments where you upload a file into ChatGPT, expecting magic… and it just stops halfway through.
No warning. No explanation. No apology. Just silence and confusion.
If your file keeps getting cut off or isn’t fully processed, here’s how to stop the chaos:
Keep It Small (yes, size matters): Files under 20MB usually work best. If your upload is dragging or only partially processing, compress it or split it into smaller parts before uploading. ChatGPT is way better with bite-sized content.
Simplify the Format: Weird fonts, dense tables, layered graphics? Yeah… those confuse the poor bot. Stick to clean, simple formatting — think plain text or lightly styled PDFs. The more straightforward your file, the easier it is for ChatGPT to actually read it.
Break It Up (Strategically): Working with a long doc? Don’t force it all in at once. Upload it in smaller sections and say something like: “Here’s Part 1 — let me know when you’re ready for the next.” It’s a much smoother ride when you give it information in manageable chunks.
That’s it for this week’s fix!
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🧱Around The AI Block
👍 15 things AI can — and can't do (so far).
🦾 Top 24 artificial intelligence applications and uses.
😱 Popular AI apps get caught in the crosshairs of Anthropic and OpenAI.
🤵♀️ Google Gemini can now handle scheduled tasks like an assistant.
🤑 Meta reportedly in talks to invest billions of dollars in Scale AI.
👩⚖️ A ban on state AI laws could smash Big Tech’s legal guardrails.
🛠️ Trending Tools
ClickUp AI automates workflows, suggests task priorities, tracks deadlines, and generates reports—all within ClickUp’s ecosystem.
Taskade lets you compose multi-agent AI workflows for writing, project planning, and data handling—streamlining complex processes.
UiPath is a leader in robotic process automation (RPA), ideal for large-scale enterprise tasks like finance, HR, and customer service.
Mistral AI offers high-performing open-source models like Mistral Medium 3 for LLM-based tasks and Devstral for coding. Available via API and major cloud platforms.
Fireflies.ai meets Otter’s offerings with transcript highlighting, smart note-taking, and deep integrations for hybrid and remote teams.
🤖 ChatGPT Prompt Of The Day: Build Your AI-Powered Strategy
AI isn't just about saving time — it's about scaling smarter. Whether you're swamped with manual processes or just looking to optimize operations, a strategic approach to automation can radically improve efficiency.
By tapping into AI for tasks like data entry, document classification, or content generation, you can streamline repetitive workflows and reallocate valuable human effort where it counts. This prompt helps you map out exactly where and how to deploy AI for meaningful impact.
Here’s How to Execute This Prompt Effectively:
Be specific: Clearly state the department or industry and the manual task you're trying to eliminate or reduce. For example, “Invoice processing in finance” or “customer support triage.”
Clarify the outcome: Mention whether your goal is speed, accuracy, cost-cutting, or all three.
Mention your existing tools: If you already use CRMs, ERPs, or databases, include those so integrations can be considered.
Ask for real tools: Request specific AI models, APIs, or RPA platforms suitable for the task.
Request a rollout plan: Ask for a phased deployment roadmap so you're not overwhelmed implementing everything at once.
Here’s an example:
You are a business automation consultant. Design an AI-powered automation strategy for [insert industry or department] that reduces manual effort in [insert specific task/process].
Include the following:
Where AI should be applied (e.g., data extraction, classification, generation)
Recommended tools, models, or APIs (e.g., OpenAI, OCR, RPA platforms)
Integration points with existing systems
Risks and mitigation strategies (e.g., accuracy, security, human oversight)
A phased rollout plan with priorities and milestones
Make sure the strategy is practical, cost-effective, and scalable.
Here’s a sneak peek:
Upgrade now to see this whole month’s prompt videos and more, or buy TODAY’S WOD for just $1.99
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