In the age of AI, it’s tempting to believe that every business process can be handed over to a chatbot. After all, ChatGPT and its AI cousins are everywhere, from writing emails to generating code, and yes, even drafting contracts. But before you let a chatbot take the wheel on your most critical legal documents, let’s pause for a reality check. Would you really trust your contracts to ChatGPT? At Cloud Contracts 365, we won’t, and here’s why.

The Illusion of Accuracy

Let’s start with the elephant in the server room: accuracy. ChatGPT is a marvel of modern technology, but it’s not a lawyer, and it’s certainly not infallible. While it can generate text that sounds legal, it doesn’t actually understand the law. It can’t interpret the nuances of your business, your industry, or the ever-changing landscape of regulations.

Imagine asking ChatGPT to draft a contract for a complex technology partnership. It might produce a document that looks impressive at first glance, but dig a little deeper and you’ll find the cracks. Ambiguous clauses, missing protections, or terms that expose your business to unnecessary risk. In the world of contracts, “close enough” is never good enough. One misplaced word can mean the difference between a watertight agreement and a legal headache.

Consistency: The Bedrock of Trust

Contracts aren’t just about what’s written—they’re about how they’re written, every single time. Consistency is key. Your business needs to know that every NDA, every supplier agreement, and every renewal follows the same standards and includes the right protections.

ChatGPT, for all its linguistic flair, is not designed for consistency. Ask it to draft the same contract twice, and you’ll likely get two different results. That’s a recipe for confusion, not confidence. At Cloud Contracts 365, we believe in the power of templates, workflows, and AI models trained specifically for legal risk, not just general language. Our platform ensures that every contract you generate is built on a foundation of best practice, tailored to your industry, and reviewed for risk every single time.

Data Security: Not Just a Checkbox

Now, let’s talk about the thing that keeps every legal and IT director up at night: data security. When you use a public AI chatbot, where does your data go? Who has access to it? Can you guarantee that your confidential contracts aren’t being used to train someone else’s AI model?

With ChatGPT and similar tools, the answer is often a resounding “maybe.” That’s not good enough when you’re dealing with sensitive commercial terms, intellectual property, or personal data. At Cloud Contracts 365, we take data protection seriously. Your contracts stay in the UK, encrypted and protected, with strict access controls and full audit trails. We’re built for businesses that can’t afford to take chances with their most valuable information.

Risks of Reviewing Contracts with ChatGPT or LLMs

Beyond drafting, the idea of using ChatGPT or other LLMs to review contracts might seem appealing. However, this approach carries significant risks:

Hallucinations and Misinterpretations: LLMs can "hallucinate" information, presenting incorrect or non-existent clauses as valid. They may also misinterpret the legal intent behind specific provisions, leading to flawed risk assessments.

Lack of Contextual Understanding: Contracts are deeply contextual. An LLM might identify a clause as risky without understanding its specific purpose within the broader agreement or industry norms.

Bias and Incomplete Analysis: LLMs are trained on vast datasets, which may contain biases that influence their analysis. This can lead to skewed risk assessments or a failure to identify critical issues.

No Legal Accountability: If an LLM misses a critical flaw in a contract during review, there's no legal recourse. The responsibility ultimately falls on the business and its legal team.

Over-Reliance and Deskilling: Relying too heavily on LLMs for contract review can lead to a decline in the legal team's own skills and judgment, making them less effective in the long run.

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The Microsoft Ecosystem: A Minefield of Acronyms

For technology businesses in the UK, particularly those operating within the Microsoft ecosystem, the stakes are even higher. Contracts related to Microsoft products and services often involve specific terms and programs that a generic LLM simply won't understand or include. These include:

NCE (New Commerce Experience): This is Microsoft's updated model for purchasing licenses. Contracts need to reflect the specific terms and conditions of NCE, including commitment periods, cancellation policies, and pricing structures.

CPoR (Customer Proof of Relationship) & DPoR (Digital Proof of Record): These relate to the process of transferring Microsoft subscriptions between partners. Contracts must clearly define the responsibilities and liabilities associated with these transfers.

TPoR (Technical Proof of Record): Similar to CPoR/DPoR, but specifically related to technical services and support.

POE (Proof of Execution): Documentation that confirms a service or project milestone has been completed as agreed. Contracts need to specify the requirements and process for providing and verifying POE to ensure all parties are aligned and obligations are met.

GDAP (Granular Delegated Admin Privileges): This is Microsoft's security model for partners accessing customer tenants. Contracts must outline the specific GDAP roles and permissions granted, as well as the security protocols in place.


A generic LLM will likely be oblivious to these Microsoft-specific nuances, potentially leaving your business exposed to compliance issues, financial penalties, or even legal disputes.

Using AI the Right Way

Don’t get us wrong, we love AI. In fact, we use it ourselves and have built it into our review tool. But we use and develop it the right way: as a tool to enhance human expertise, not replace it. Trained on real lawyer knowledge and thought processes and kept out of the reach of LLMs, our AI models are trained specifically to spot legal risks in contracts, flagging issues for your review, consistently and accurately, rather than making decisions for you. You stay in control, with the peace of mind that comes from knowing your contracts and your business are secure.

The Bottom Line

Would you trust your contracts to ChatGPT? We won’t. And neither should you. When it comes to the documents that define your business relationships, protect your interests, and keep you compliant, there’s no substitute for a platform built for the job. At Cloud Contracts 365, we combine the best of AI with the rigour of legal expertise and the security your business demands.

Ready to see the difference? Let’s talk, no chatbots required.

Book a demo with one of our experts to discover more: Book a demo