The Broken Promise: How ChatGPT’s System Failures Are Undermining Professional Work

By Dr. Wil Rodriguez

For Tocsin Magazine

In an era where artificial intelligence has become integral to professional workflows, the reliability of AI systems has moved from convenience to necessity. Yet, OpenAI’s ChatGPT—arguably the most widely adopted AI assistant—continues to plague its paying subscribers with systematic failures that can destroy hours, days, or even months of work with little warning and no recourse.

The File Expiration Crisis

Imagine this scenario: You’ve spent five hours waiting for ChatGPT to generate a critical video file for your work. The project deadline looms, colleagues are waiting, and your professional reputation hangs in the balance. Just as the system completes the processing, you receive the dreaded message: “It seems that some of the files you’ve previously uploaded have expired.” The file you desperately needed has vanished into the digital ether, taking your time, effort, and potentially your deadline with it.

This isn’t an isolated incident—it’s a systematic problem that has become endemic to ChatGPT’s architecture. Files are deleted automatically after a short TTL (time-to-live) window, and if the file finishes while you’re away or distracted, it’s gone. For professionals who rely on ChatGPT for critical work, this represents a fundamental breach of trust.

The Pattern of Neglect

The most disturbing aspect of these failures isn’t their technical nature—it’s OpenAI’s apparent indifference to their impact on paying customers. User complaints on OpenAI’s own developer forums paint a picture of systematic neglect and broken promises. One frustrated subscriber wrote: “You’ve ruined everything I spent months and months working on. All promises of tagging, indexing and filing away were lies.”

The file expiration problem has intensified recently, with users reporting that documents are “almost instantly expiring” due to what ChatGPT claims are “new rules from OpenAI” for data privacy reasons. Yet these same policies seem inconsistently applied, creating confusion and unpredictability for users who have paid for reliable service.

System-Wide Outages: When AI Dependency Becomes Liability

Beyond file management failures, ChatGPT has experienced numerous significant outages that leave millions of users stranded. ChatGPT suffered an unexpected outage on June 10, 2025, following a pattern of service disruptions that have become disturbingly routine. The impact of ChatGPT downtime on December 12, 2024, underscored the growing reliance on AI tools in various sectors, highlighting the need for resilient systems and effective contingency plans.

What makes these outages particularly problematic is their unpredictable duration and OpenAI’s often inadequate communication about resolution timelines. Users report systems being down for days without clear restoration schedules, leaving professionals scrambling to meet deadlines with alternative solutions.

The Code Interpreter Catastrophe

For users who rely on ChatGPT’s code interpreter for data analysis, file processing, and automation tasks, the system’s unreliability becomes even more pronounced. The “Code interpreter session expired” error has become a common frustration, with users reporting that download links fail to generate, accompanied by cryptic “GetDownloadLinkError” messages.

This technical fragility represents a fundamental design flaw in a system that markets itself as suitable for professional use. When critical work products can disappear without warning due to session timeouts or system resets, the tool becomes not just unreliable but actively counterproductive.

The Customer Service Void

Perhaps most troubling is OpenAI’s response—or lack thereof—to these systematic issues. Despite numerous user complaints and documented problems spanning months, users report feeling ignored, with some demanding refunds and ETAs for fixes that never materialize. The company’s approach appears to be one of damage control rather than genuine problem resolution.

For paying subscribers who have integrated ChatGPT into their professional workflows, this represents a breach of the implicit contract between service provider and customer. When users pay premium prices for AI assistance, they have a reasonable expectation of reliability and support.

The Real Cost of AI Unreliability

The implications of ChatGPT’s reliability issues extend far beyond individual inconvenience. In professional contexts, these failures can result in:

• Missed deadlines that damage professional relationships and business opportunities

• Lost productivity from hours of work that must be repeated due to system failures

• Reputational damage when AI-dependent workflows fail at critical moments

• Financial losses from subscription fees paid for unreliable service

• Strategic risk from over-dependence on fragile AI infrastructure

A Call for Accountability

The AI revolution promises to transform how we work, create, and solve problems. But that promise is undermined when the very systems we’re asked to trust prove fundamentally unreliable. OpenAI has positioned itself as a leader in this transformation, accepting billions in investment and millions in subscription revenue based on commitments to reliability and utility.

It’s time for the company to be held accountable for the gap between its promises and its performance. Paying customers deserve:

• Transparent communication about system limitations and planned maintenance

• Reliable file persistence that doesn’t arbitrarily delete user work

• Robust customer support that addresses problems rather than deflecting them

• Service level agreements that provide recourse for system failures

• Alternative solutions or compensations when critical failures occur

Moving Forward: The Need for AI Reliability Standards

As AI becomes increasingly central to professional work, the industry needs to develop and enforce reliability standards that protect users from the kind of systematic failures that have plagued ChatGPT. This isn’t just about better engineering—it’s about establishing a framework of accountability that ensures AI providers can be trusted with mission-critical work.

The current situation with ChatGPT serves as a cautionary tale about the risks of AI dependency without appropriate safeguards. Until OpenAI addresses these fundamental reliability issues, professionals would be wise to maintain robust backup systems and alternative workflows that don’t depend on the company’s demonstrably fragile infrastructure.

The promise of AI assistance is real and valuable. But that promise cannot be fulfilled by systems that regularly fail their users at critical moments. It’s time for OpenAI to match its ambitious vision with the boring but essential work of building truly reliable systems.

Author’s Reflection

As the author of this piece and a longtime user of AI systems in education, creative production, and research, I write this not in anger, but in deep frustration—and a sense of professional responsibility.

AI, when reliable, can be transformative. But when it fails at the structural level—without transparency, recourse, or respect for the user’s time—it becomes a betrayal of the trust that fuels innovation. This article was born out of repeated lived experiences that no professional should have to endure. If we are to embrace AI as a partner in our work, then we must also demand that it act with the consistency, respect, and support we’d expect from any real collaborator.

What I’ve described here is not the failure of a tool—it’s the breakdown of an agreement between creators and the systems we rely on. And that matters.

Invitation to Explore

If this article resonated with you, I invite you to explore other thought pieces in Tocsin Magazine, where I regularly publish essays on education, ethics, AI, and the future of creative and intellectual work.

These articles are written not just to inform—but to provoke, awaken, and invite you into a conversation about what kind of future we are building together.

Join the dialogue. Read deeply. Share boldly.

You’ll find my latest work there, and I hope it adds light to yours.