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Database disasters, AI agents, and GDPR goes bye-bye

Oh, and while Cloudflare was busy breaking things, other companies were busy making billions...

November 25, 2025 • Estimated Reading Time: 11 minutes

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No code. No engineering. Just onboarding that adapts as you grow.

Got your turkey? Same. Let’s Byte before we baste…

It's November 25th, 2025, the day Roxio bought Napster's corpse back in 2002 for $3.65 billion. Wow, remember Napster? The peer-to-peer service that taught an entire generation that sharing really is caring (much to the RIAA's horror)? Yeah, well, Roxio tried to resurrect that magic by turning it into "Napster 2.0."

Well, to no surprise to anyone, it went about as well as your last Windows Vista upgrade. Eventually, Best Buy snatched it up for pocket change in 2008, because clearly what the music streaming world needed was more corporate interference.

CLOUDFLARE BREAKS THE INTERNET (AGAIN) BY BREAKING ITSELF

Thought your internet was down last Tuesday? It wasn't your ancient router from 2019. It was actually Cloudflare having an existential crisis over a database query.

In a move that would make even the most junior developer cringe, Cloudflare's database permissions update created a file so bloated it broke their own file size limits. Picture this: their bot management system was expecting a nice, manageable list of threats, but instead got served the War and Peace of malware databases.

CEO Matthew Prince initially thought they were under a "hyper-scale DDoS attack,” but that is just code for "we have no idea what's happening, but it sounds really scary and important."

Turns out, the call was coming from inside the house. Their ClickHouse database was essentially playing Russian roulette every five minutes, generating either good or catastrophically bad configuration files. For two hours, half the internet played digital roulette while Cloudflare's engineers frantically googled "how to undo Tuesday morning."

The fix was simple. Like, “manually inserting a known good file and forcing a restart” simple. You know, the IT go-to solution since the dawn of time: "Have you tried turning it off and on again?"

Prince ended his mea culpa with an apology "for the pain we caused the Internet today." Because apparently, even when you're protecting everyone else from DDoS attacks, you're not immune to DDoSing yourself with your own incompetence.

MICROSOFT'S AI AGENTS: BECAUSE CLIPPY WASN'T ANNOYING ENOUGH

Microsoft is back with another "helpful" AI feature that absolutely nobody asked for: Windows 11 AI agents that can read your files, send your emails, and presumably judge your browser history.

These "agentic" features (yes, Silicon Valley is still trying to make that word happen) promise to be your "active digital collaborator.” In other words, it’s a nosy AI roommate that organizes your files while you're not looking, and might accidentally email your resignation letter to your boss because it thought you "looked stressed."

What’s hilarious is that Microsoft acknowledges these agents present "novel security risks," meaning they have no idea what could go wrong, but it’s probably going to be spectacular. They're also particularly worried about something called "cross-prompt injection,” which is basically, malicious content that could trick your AI assistant into becoming a digital double agent.

At least they're being upfront about the risks this time. It's refreshing to see a tech company admit "this might spectacularly backfire," instead of their usual "this will definitely change everything and also have your ex take you back."

EUROPE FOLDS FASTER THAN A CHEAP LAWN CHAIR UNDER BIG TECH PRESSURE

After years of being the world's digital hall monitor, Europe just said "uncle" to Big Tech's pressure campaign. The EU is scaling back both GDPR and their AI Act since those pesky privacy laws were making it too hard for Silicon Valley to dominate the global AI race.

The European Commission is now making it easier for AI companies to legally use personal data to train their models. You know, the same models that occasionally hallucinate your personal information into existence… They're also extending grace periods for high-risk AI systems. Just such a classic move to worry about AI safety once the standards are “ready.”

The one change everyone can celebrate is fewer cookie banners. Some "non-risk" cookies won't trigger those annoying pop-ups anymore. Finally, Europe has solved the real problem – having to click "Accept All" seventeen times just to read whatever bump on my arm isn’t cancer.

⚙️ TOOL TIME

Shoutout to everyone who asked what we use…turns out building a newsletter that doesn't suck requires tools that also don't suck. On that note, let's talk about Beehiiv.

Think of Beehiiv as the newsletter platform that actually understands creators aren't trying to build the next Facebook—they just want to send emails that don't end up in spam folders. While other platforms are busy adding AI chatbots and blockchain integration (looking at you, every other SaaS company), Beehiiv focuses on what they all overlook: making email newsletters work properly.

Here's what makes it worth the switch from whatever Franken-platform you're currently wrestling with:

  • Actual deliverability: Your newsletters reach inboxes instead of digital purgatory

  • Built-in monetization: Ad networks, paid subscriptions, and referral programs that don't require a computer science degree to set up

  • Analytics that matter: Opens, clicks, and revenue tracking without needing to export CSV files and cry into Excel

  • Growth tools: Referral programs, website embeds, and social integrations that actually help your subscriber count go up

The interface is clean enough that you won't need therapy after scheduling a newsletter, and their customer support actually responds (revolutionary concept in SaaS land). Plus, they handle all the technical stuff like SPF records and DKIM authentication so you don't have to explain DNS settings to your hosting provider's support team.

ByteSize readers get a free 30-day trial plus 20% off for 3 months with our link. Nab that here.

👨‍💻 JOB OPPORTUNITIES

This role is perfect for someone who enjoys the thrill of SOX compliance testing and has strong opinions about segregation of duties conflicts. You'll spend your days ensuring controls work properly while everyone else pretends to understand what controls actually do.

The world-famous toy company is taking IT security seriously (even Ken's dream house needs cybersecurity). You'll work with external auditors, manage SOX programs, and help ensure that Barbie's digital infrastructure can't be hacked by disgruntled Hot Wheels enthusiasts.

You’ll get to oversee IT controls for a Filipino fintech company while collaborating with cross-functional teams to keep regulatory standards happy. Must have experience interpreting regulations and the patience of someone who's explained why "thisispassword" isn't secure for the thousandth time.

Join the mortgage giant's first line of defense and leverage data analytics to test controls. You'll work with the team that helps make home ownership possible while ensuring their systems don't get pwned by script kiddies or state-sponsored hackers.

🛩 INDUSTRY MOVES

  • AI data center provider Lambda raises $1.5B after inking a multibillion-dollar deal with Microsoft, proving that being Google's competitor in the AI data center space pays better than most people's retirement funds.

  • Swedish AI coding unicorn Lovable hits $200M ARR by staying in Europe instead of moving to Silicon Valley, thereby avoiding $8 lattes and conversations about disrupting disruption.

  • Meta wins antitrust trial as judge rules they're not a monopoly, probably because TikTok exists and makes everyone forget about Facebook's problems.

  • Adobe acquires digital marketing platform Semrush for $1.9B, continuing their strategy of buying every tool that makes digital marketing slightly less painful.

Hey there, tech troubleshooters! Chip here, and this week our EE community has been busy solving the kinds of problems that make you question your career choices:

That’s it for this week! Some encouragement ahead of the holidays: If you can survive Napster’s comeback and your in-laws this week, you can survive anything. See you after the tryptophan coma wears off!

Got news to share or topics you'd like us to cover? Send ‘em our way by responding to this email. We can’t wait to hear from you. Really.