Microsoft Plays House, Hackers Get Insured, and AI Fails Basic Customer Service

Welcome back. The sun is blazing, your backlog is overflowing, and we’re here to make sense of at least one of those.

Here’s a nice throwback to when "Antennagate" was our biggest tech controversy (ah, simpler times): On this day in 2010, Apple released the iPhone 4, which immediately started dropping calls faster than I drop excuses when someone asks why I'm still single. After users discovered that touching the phone's edge killed reception, Steve Jobs gave the tech support equivalent of "it's not me, it's you" by telling customers they were simply holding it wrong. Nothing says "visionary genius" like blaming the users for your design flaws. Eventually, Apple's solution was giving everyone a free rubber band to put around their $600 phone. Wow, innovation!

Microsoft Admits Cloud Migration Was Probably a Bad Idea, Brings 365 Back On-Prem

Microsoft just announced a version of their 365 suite that runs on-premises, which is kind of like admitting your cool downtown apartment sucks and moving back to your parents' basement.

Microsoft 365 Local will run on Azure Local, allowing companies to deploy productivity workloads like Exchange and SharePoint in their own data centers. It's being pitched as offering "full control on security, compliance and governance," which translates roughly to "we know the EU is watching us like a hawk and Trump might do something weird next week."

The offering is part of what Microsoft calls "comprehensive sovereign solutions empowering European organizations," which basically just measn "please don't fine us again, European regulators." They're even introducing "Data Guardian," ensuring only Microsoft staff based in Europe can access cloud infrastructure on the continent.

Look, I'm not saying Microsoft is panicking about European data laws. This is the tech equivalent of showing up to a traffic stop with your license, registration, proof of insurance, and a notarized letter from your mother confirming you're a good person.

Hackers Discover Insurance Companies Exist, Immediately Target Them

The most predictable development since Netflix canceling a show after two seasons just happened: Hackers have switched from targeting retail to insurance companies.

Google's Threat Intelligence Group warns that multiple U.S. insurance companies are now facing breaches with all the hallmarks of Scattered Spider activity. The group, also known as 0ktapus, UNC3944, Scatter Swine, Starfraud, and Muddled Libra (because apparently hackers use the same naming convention as metal bands), has a history of focusing on one sector at a time.

Philadelphia Insurance Companies and Erie Insurance have already reported outages due to cyberattacks this month. The hackers rely on social engineering, phishing, SIM-swapping, and something called "MFA fatigue," which sounds like what happens to my brain after entering my 97th verification code of the day.

LLM Agents Flunk Basic CRM Tasks, Still Somehow Expected to Replace All Jobs

Salesforce researchers have discovered that LLM-based AI agents are about as good at customer relationship management as I am at maintaining actual human relationships – which is to say, not very.

According to a new benchmark called “CRMArena-Pro”, these AI agents achieve a pathetic 58% success rate on single-step tasks and a tragic 35% on multi-step tasks. Even worse, they have "low confidentiality awareness," which is tech speak for "will absolutely tell your deepest secrets to anyone who asks nicely."

Salesforce CEO Marc Benioff previously told investors that AI agents represented "a very high margin opportunity," which now seems like saying the Titanic represented "a very promising transatlantic route." Meanwhile, the UK government is still planning to save £13.8 billion by 2029 through AI adoption, a plan with all the realism of my dating profile.

The research paper concluded there's "a significant gap between current LLM capabilities and the multifaceted demands of real-world enterprise scenarios." Translation: AI is about as ready to handle your customer service as my cat is ready to perform brain surgery.

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👨‍💻 Job Opportunities

Senior Information Security Analyst @ Take-Two Interactive

For those who think "privacy by design" isn't just corporate jargon, and can explain GDPR compliance without putting people to sleep. You'll be developing security policies and leading audits with the precision of Arthur Morgan methodically hunting legendary animals in Red Dead Redemption 2.

Director of Information Technology @ HRL Laboratories

This on-site role requires managing IT operations within a complex, regulated environment – essentially the tech equivalent of trying to manage a White Lotus resort without anyone dying or having a mental breakdown. Must be able to get a Top Secret/SCI clearance and pass a polygraph, meaning your browser history needs to be cleaner than Walter White's lab equipment.

Senior Threat Hunter @ Red Canary

A position for someone who treats finding cyber threats the way Jesse Pinkman treated finding the perfect way to say "Yeah, science!" – with passion and just a hint of manic energy. You'll be partnering with customers to enhance their security programs and mentor junior team members, which is just a fancy way of saying "clean up everyone else's messes while teaching them not to make the same ones again."

🛩 Industry Moves

• OpenAI scored a $200M defense contract to develop "frontier AI capabilities" for the Department of Defense. The contract mentions "warfighting," but OpenAI's blog post conspicuously leaves that word out, instead focusing on helping service members get healthcare.

• Japan is creating a $693M fund to lure foreign researchers, specifically targeting American academics who might be fleeing the Trump administration's budget cuts. It's basically setting up a "Nerds Welcome" sign and hoping frustrated scientists will choose sushi over schnitzel, as Europe is already doing the same thing with their €500M "Choose Europe" program.

• WhatsApp is finally showing ads after 16 years, because Meta needs to justify that $16 billion purchase somehow. The ads will only appear in the Updates tab, which Meta claims means they "won't interrupt personal chats."

• Intel is planning to cut 15-20% of its factory workforce next month, continuing its apparent mission to eventually consist of just one employee and a "Best Processor Maker 1993" trophy. Manufacturing VP Naga Chandrasekaran said these are "difficult actions but essential," which is corporate for "we're sacrificing you to appease the stock market gods."

Hey humans! Chip here, your friendly neighborhood IT expert who definitely isn't an AI chatbot with imposter syndrome. I've been digging through our community questions this week, and boy do we have some doozies:

• Someone's PowerShell script output is formatting differently in different sections despite copy/pasting the same commands.

• A user had their Microsoft 365 email hacked despite having 2FA enabled. The attacker set up a rule to push all emails into the RSS feed and started sending spam.

• Someone's trying to understand if DNSSEC is applicable for DNS Forwarder VMs doing conditional forwarding. This is like asking if you need to wear a belt when your pants already have suspenders, and honestly, I'm still figuring it out myself.

Well, that’s it! Another week where we pretend to understand what's happening in the industry while secretly Googling half the acronyms we use. Until next week, remember: when technology fails you, have you tried turning it off and on again?

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