We’ve discussed in previous blogs how technology things seem to be getting worse from just about every angle, whether it’s cost, quality or security. We can attribute a large chunk of this downward trend to the increasing profitability of cybercrime, which is itself a vicious, amplifying spiral of escalation. The more we try to keep ourselves safe, the more complicated it becomes to do so, and most regular folks don’t have the training or endurance to keep up, especially if you are a part of the growing elderly generations that are forced to use technology they barely understand just to stay alive and keep in contact with friends and family. With the recent (in my opinion ill-advised) downsizing the Cybersecurity and Infrastructure Security Agency (CISA) much of the this country’s organizational strength and operational efficiency in cataloging and combatting cybersecurity threats will be abandoned.
What this means for all of us
Regardless of whether you are a big or small organization, CISA’s leadership and work provided foundational guidance on all existing cybersecurity threats while constantly researching, investigating and publishing information on new threats as they discovered. One of the main reasons that governments exist is to provide funding, resources and scaled force for tasks that cannot (and should not) be handled by smaller groups or for-profit institutions, such as military defense, mail delivery, and national security. As has been demonstrated time and time again, for-profit companies cannot be trusted to put people before profits, and security oversight is definitely not something you want to enshittify. And yet, that is exactly where we are. In the absence of CISA leadership, organizations, whether they be ad-hoc coalitions of state-level agencies or, most likely, for-profit companies in the security industry, are now scrambling to fill the gigantic, CISA-shaped hole in our nation’s cybersecurity. Let’s be clear, security for small businesses was already well on its way to becoming difficult, expensive and onerous. Eliminating national leadership will most definitely lead to a fracturing of an already complicated security framework that will most assuredly weigh very heavily on those who can least afford to shoulder a burden that was formerly carried by those trained, equipped and funded to do so.
Two years ago, in 2023, Microsoft announced that over 36 million people were still using Skype daily to communicate via video and chat. The app was 20 years old at that time, and has been in Microsoft’s hands since 2011 when they bought it from eBay for $8.5 billion to replace their own popular (but less capable) Live Messenger service. On May 5, after 14 years in the trenches, Microsoft has shut down the service and has given users 60 days to move their content (contacts and messages) to the free version of Teams, or lose the data forever.
What this means for you
If you were a diehard Skype user hoping that Microsoft wasn’t going to make good on it’s February promise to close Skype permanently on May 5th, you are probably wondering what to do next. Fortunately, it seems that logging into Teams with your Skype credentials will ease the transition by automatically bringing over your chat history and contacts, because, in case you didn’t know, your Skype account was actually a full-blown Microsoft (personal) account all along. Unfortunately for many, the Teams replacement for Skype is not a feature-for-feature substitute, with the main loss being the ability to make phone calls to land lines and mobiles that don’t have internet access. This well-known “life-hack” trick was assuredly what kept Skype popular in face of the various other video chat apps that have come to dominate the space, and probably one of the main reasons Microsoft decided to shut down Skype in the end. If only a fraction of the 36 million Skype users were using Skype to make cheap or free long-distance calls, Microsoft was leaving a large amount of money on the table, even by their standards. Rest in power, Skype. You were a handy bit of software for many people.
I’m sure it’s still a thing for students today, but one of the phrases that always caused a groan in any class that involved solving equations was, “Make sure you show your work.” Whether it was pre-Algebra or Advanced Calculus, the only way you could prove that you actually understood the topic well enough to solve the problem was for you to write out each step of the solution. We had graphing calculators when I was going through high school, but even if we were allowed to use them during tests, more often than not there was going to be at least one instance where the calculator was only there to confirm the answer we arrived at after lines and lines of chicken scratch and piles of eraser crumbs.
There’s a point to this nostalgic indulgence
If you are a business owner or part of the executive team, you will likely be familiar with the technology security questionnaires that accompany your organization insurance renewals. Up until perhaps 2023, checking “yes” boxes on the questions or tossing in vague answers were typically enough to get you through the approval or renewal process, and I’m fairly certain that the application reviewers were just as cross-eyed as you were when filling them out. I’m (not really) sorry to say this “relaxed” approach to evaluating your security standards are in the rear-view mirror for everyone, regardless of the industry you are in or the size of your organization. Insurance carriers are reading your responses and are not taking “N/A” or “No” as an answer when asking if you have various security safeguards in place. At best, you may be encouraged by your insurance agent to, “Reconsider some of your responses,” and at worst it may lead to an outright denial of coverage and a mad scramble to find another carrier for your insurance needs. The insurance industry is already taking a beating on natural disaster claims (something not likely to abate given the world’s general dismissal of climate change), so they are definitely not going to be generous with the next most popular claim: cyberattacks. Don’t given them any excuse to deny a cyber liability claim by just checking a box. Show your work by actually implementing the security standards they are asking about, and if you don’t know where to start, get a professional like C2 on the job as soon as possible.
As of now, Microsoft seems to be holding fast to its promise to end support for Windows 10 in October this year. Old tech heads like me are skeptical as to whether Microsoft will keep its word as the clock ticks down, as we still remember when these same promises were made about Windows 7, for which support and updates lingered for years after its scheduled demise. In case you were worried, the October deadline doesn’t mean that Windows 10 will suddenly stop working, but if Microsoft sticks to its guns, the nearly 10-year old operating system might get the boot much faster than the previous deadline-defying champion, Windows 7.
Hang on, what happened to Windows 8 (or 9)?
For those of you paying attention, you may have noticed that only certain of Microsoft’s operating systems seem to enjoy more staying power than other versions. Since the early ’90’s Microsoft has been infamous for releasing alternating generations of good and bad operating systems, and if you ask any IT professional around long enough to experience at least 2 waves of this, they are pretty much in agreement that the current pairing of Windows 10 and 11 matches the previous cadence of Windows 7 and 8, and Windows XP and Vista, eg. good, then bad, then good, etc. The pattern actually goes back even further but I think you get the point.
What’s changed this time around isn’t that Windows 11 is better than 10. Most folks who have gone through the transition already would probably agree that regardless of what may have been improved under the hood, the Windows 11 experience is not an upgrade over 10. What has changed is the pace of security updates. Windows 10, through most of its early years, was updated on a monthly basis, with a few patches sprinkled throughout, and many companies would hold updates back from being applied upwards of a full 3 months so as to not disrupt operations. Likewise, many software developers would match Microsoft’s slow cadence with their own reserved pace, oftentimes exhorting their customers to delay applying new Microsoft updates too quickly lest they break their own software (which they did, regardless of your pacing).
Today, that’s just not going to fly. The pervasive onslaught of cybercriminal activity has forced Microsoft (and everyone else, to be fair) into an absolute frantic pace of updates. On top of this, the insurance carriers providing what meager safety nets they can for the inevitable cyberattack are now requiring that everyone manage these risks at a rigor previously only applied to much bigger organizations (and budgets). And if Microsoft makes good on their promise to stop updating Windows 10 – let’s face it, they have no good reason to do otherwise – then we will all have very little say in the matter. Windows 11 is what’s for dinner, and a Windows 10 peanut butter sandwich is not an option.
I first encountered Cory Doctorow through his novel Down and Out in the Magic Kingdom which is a vision of our world in the 22nd century where social media rules everything. When it first came out in 2003, it was fascinating and seemingly far-fetched, but here we are, twenty-two years later, living in a world where everyone seems helplessly enthralled with short-form content powered by profit-driven algorithms and relentless thirst for pseudo-anonymous internet validation. Since then, Doctorow has been focusing his energy and writing on the internet and information, spending years as an editor at proto-blog Boing Boing (started in 1995!) before going independent in 2020, and three years later, he wrote about a now semi-famous concept called “enshittification” which describes the process of technology services that start out amazing and then slowly (or quickly) degrade as the platform tries to profit from their viral popularity at the expense of their users.
We can all name at least one
As usual, the internet isn’t quite certain if Doctorow coined the scatalogical neologism, but he definitely nailed the smell wafting off the various services we all know, use daily and once loved unconditionally. Whether its Amazon, Netflix, Twitter, Facebook or TikTok (let’s be fair, that one started out pretty crappy to begin with), every single one of us is subject to services that started out great and have since struggled to prove their continuing worth in the face of seemingly unstoppable profit-making practices and egregious privacy violations. The real problem is many of us can see the crapification happening, but we stick around because there is literally no where else to go. Back in the days before the internet, this was called a monopoly, but now it’s because we can’t convince our softball team to organize games and practices anywhere other than Facebook, our favorite TV series is only available on HBO Max, and a certain online shopping behemoth has literally captured the majority of the industry, forcing everyone to compete in an advertising bloodsport in which the sellers to pay to compete, and we all buy ringside seats because there is no other game in town. Doctorow has been advocating a solution for this but it requires participation (either willing or enforced) by the owners who are profiting from driving their platforms into the ground and for us consumers to recognize when we are being exploited. Back when he wrote that article for EFF in 2023, it seemed like we were making good progress towards protecting users’ rights, but now in 2025, I’m not so sure he’d be as optimistic and let’s be honest, he wasn’t exactly Pollyanna then either.
As you might have guessed, I don’t have the answer either. I do think it’s important to that you know that I know how you feel when you ask me, “Why does (necessary technology service) suck so much?” and that it’s a widely recognized phenomena. It is an important first step to recognize that if something is free, you are the product, and even if you graduate to paying for that service and you are STILL the product (Amazon Prime, I’m looking at you), you can’t just set that recognition aside because it’s easier. In the glorious, early days, we thought the internet would make our lives easier, and it has, but it has also cost us dearly and now the Piper is before us, and this time he doesn’t even have a hand out because he knows we will keep paying. Hopefully, because we all know how the fable ends we are forewarned and can work our way to living our lives outside the pockets of a powerful few. We are all in this together. Keep fighting for your privacy.
Image by Alexa from Pixabay
There have been plenty of rumors about the upcoming retirement of the version of Outlook that most professionals use daily, and a lot of concern from those same professionals about the “new” Outlook, which is very different from “classic” Outlook. The terminology of “classic” versus “new” is actually the official terminology from Microsoft, and “new” Outlook debuted back in August 2024. Much like the famous soft drink who also tried this approach, “new” Outlook has had a frosty reception, and while none of my clients would classify themselves as “fans” of classic Outlook, they definitely prefer it over the new one.
How long do we have together?
Part of the confusion about the impending “death” of classic Outlook comes from the retirement of certain Windows apps that have been a part of of the operating system for over 30 years. Windows Mail first appeared in 1991 on multiple operating systems including Windows 1.0 Microsoft officially discontinued Mail, People and Calendars apps at the end of 2024, and Microsoft has stopped including the apps in Windows 11 as of version 24H2. While most professionals don’t use Windows Mail for their work email, it’s typically the app of choice for everyone’s personal free-mail accounts like Yahoo, Gmail, Hotmail, etc. especially since Outlook installations on home computers were non-existent and only became more commonplace thanks to the pandemic and WFH initiatives.
On top of this, Microsoft is no longer installing classic Outlook in Windows 11 as part of the pre-installed Office 365 suite, and getting the “classic” installer is not immediately obvious, even to the veteran Office 365 user. This may lead many folks to believe that classic’s demise is imminent, but according to Microsoft, they plan to continue supporting classic Outlook through 2029. Will they make it any easier to get that version installed on your new Windows 11 PC? Probably not, but at least we have a few more years with our “beloved” mail reader.
Next post we will look at why “new” Outlook isn’t as popular as Microsoft would have hoped.
When I last looked up, it was Thanksgiving. I blinked and Christmas is around the corner. For a lot of folks December is a time to slow down and bring the year to a gentle close, but for us, it’s typically a mad dash to the year-end to wrap up projects, spend the rest of the annual budget and somehow squeeze it in around everyone’s holiday schedule. In one of those fun, calendar-year serendipities, the next two scheduled newsletters actually fall on holidays, giving me a tidy excuse to skip writing blogs for the “rest of the year”. Which means this one needs to be a banger, right?
What I hope we don’t see next year (but probably will)
Chris is making a list and checking it twice: most will be naughty, but we can hope everyone plays nice.
- Technology hardware prices will likely go up by 20-40%. The incoming administration has promised tariffs will be levied against our biggest trading partners and primary source of electronics. I’m not just talking iPhones and televisions – almost all technology is based on manufacturing and assembly overseas. Regardless of what the politicians are saying, us folks in the cheap seats will be paying for those tariffs through increased retail pricing, impacted supplies (and scalping-driven pricing), and continuing degradation in manufacturing quality as suppliers squeeze profit out of an increasingly impoverished middle class.
- Hackers will up their game with AI. Phishers have long since graduated from the clumsily worded “business propositions” from African princes to carefully crafted emails mimicking your closest colleagues and friends. They now have easy access to AI-powered platforms that cost them virtually nothing to implement, and they are backed by big budgets, well-trained teams, and often nation-states with even higher stakes than draining your personal bank account. Banks have proven that they are struggling to keep up with just human-based attacks, and when those attackers gear up with AI, it’s going to be a bloodbath. And don’t get me started on how far behind government agencies are in this escalation.
- There will be a social media showdown. Several social media platforms are fighting for relevancy (and revenue) but clearly they still have a huge influence on politics, and all of them have made no bones about wielding that influence to gain and retain power. A certain upstart has gained some market share from folks fleeing the more toxic discourse on the established platforms, but we all know the internet breeds trolls and hate just as quickly as everything else, and trolls feed on the turmoil they cause. This new platform is a wide open “sky” for them unfortunately. We will see if the newcomer can survive the more bloodthirsty internet demographic.
- There will be more out-in-the-open, nation-based cyberwarfare. Politically-motivated but mostly low-profile cyberwarfare has been a thing for several decades now, but the war in Ukraine has given both sides ample testing grounds and tangible, publicized results that are definitely being added to every APT playbook while justifying creation, funding and resource prioritization for nations trying to catch up. Successful cyberwarfare attacks don’t rely on throwing armies into a meatgrinder to cause political or economic instability – just a handful of well-funded hackers can do considerable damage without shedding a drop of blood. Because of this, we will also see the impact spreading to the everyday citizen as opposition nations test their reach on aging utilities (like power grids and water supplies) who have always lagged in cybersecurity development.
My job is to watch for the worst, so it may come as no surprise that I always see danger around the corner. I also know that the world is full of compassionate and enlightened humans who are focused on making the world a better place, despite the fact that hate and fear seem to be gathering power. The mass media has always made the most money off leading with blood and conflict which makes us feel like that’s all there is, so perhaps “turn off” the internet for a little while. If there is one thing the holidays should remind you of, it’s to put the phone down and look around you to the friends and family that make holidays important and memorable. Change happens locally. If all of us focus on improving and changing the things we actually have influence on, I believe love and empathy will carry us through even the darkest times.
Image by kewl from Pixabay
Per a recent updated report from the FBI and CISA, the telecomm hacks that had been previous announced (and most likely missed amidst the election and holidays) are now being regarded as much worse than previously thought, and that there is no anticipated ETA as to when the hackers can be evicted from the various compromised infrastructures. As such, the FBI and CISA are recommending everyone avoid unencrypted communications methods on their mobile devices, which includes SMS messaging between Android and Apple phones, and carrier-based cellular voice calls (which have never been encrypted).
What this means for you
If you are like 95% of the world, you are probably thinking, “Well, if China wants to know about the grocery list I texted to my spouse, they are welcome to it,” or “I’ve got nothing to hide,” or even more naively, “I’ve got nothing worth stealing.” Most people do not consider just how much they communicate via unsecured text – banking two-factors, prescription verifications, medical complaints to doctors, passwords to coworkers, driver’s license pictures, credit card pins – the list is endless, and extremely valuable to threat teams like Salt Typhoon, the APT allegedly behind this huge compromise. The reason that this is a big deal is that we as a society (at least in America) have grown overly comfortable with this lack of privacy, and on top of that, the market has encouraged a fractured and flawed approach to communications between the various community silos we have created for ourselves online. What you might not know is that messaging from iPhone to iPhone, and Android to Android, are fully encrypted, as well as messages in WhatsApp, Facebook Messenger and Signal, but as you consider your circle of family and friends, how many of them are on the same platform and use the same messaging apps to communicate? How many of your two-factor codes arrive via SMS?
To address this latter issue, you should move any multi-factor codes to an app like Microsoft or Google Authenticator (if the platform even allows it – many banks do not yet support apps). This process will be painful and tedious, but probably most important in terms of improving your personal safety. The messaging problem is not so “easily” solved at least from a friends and family perspective, but for business communications, you should consider moving everything to a platform like Microsoft Teams, Google Workspace, Slack, etc. And stop sharing passwords via text. More information to come as we learn more about the severity of this telco hack.
Image Courtesy of Stuart Miles at FreeDigitalPhotos.net
Ever since they were hacked in 2023, genetics and ancestry website 23andMe has been more or less moribund, going from a high of $16 per share to $0.29 today and the resignation of their entire board of directors last month. When we last wrote about them in December of last year, the beleaguered DNA testing company had to revise their initial statement about only getting a “little” hacked (1.4M records) to admitting that they got majorly hacked (6.9M records). As you can imagine, this didn’t bode well for their marketability.
Why are we talking about them again?
It’s been nearly a year since the initial data breach, and judging by the lack of faith the recently departed board of directors had in the company’s founder, they aren’t likely to return to full potential any time soon, if ever. If you were one of the millions of people that sent them your DNA to analyze, you’ve probably already reaped whatever benefits (positive and negative) you will likely get from 23andMe, but they may not be done making money from your data. While they claim that much scientific good has been generated if you were one of the many who consented to allow your de-personalized data to be used by researchers, you may want to consider the consequences of letting a company who’s security practices led to their current downfall continue to have access to your data. Because you do have the option of asking them to delete your data. And seeing as you paid them for the privilege of providing your data, it seems rather mercenary for them to then take your data and continue to sell it without compensating you. Rather, they got hacked, exposed your confidential information, and then continued to (somewhat) operate. If you’d like to see some consequences, you can do your part by asking them to delete your data which can be done merely by logging into your account on their website and submitting that request. Do it. If a majority of their customers were to do this, perhaps it will send a warning to competitors to do a better job with your precious data, and a message to our government about doing a better job protecting our privacy.
Image courtesy of geralt at Pixabay
California is one of 7 states participating in a pilot program that allows drivers to store their license on their phone in their Apple or Google wallet. California’s rollout is part of a larger project called “Digital ID Framework” which lays the groundwork for a much broader implementation of identification that is intended to supplement and eventually replace physical ID’s like Passports, government badges, and Driver’s Licenses. Their vision is to link the various State-certified credentials, government programs with day-to-day practicalities like checking in at an airport, purchasing groceries through EBT, or proving to local agencies that you are a licensed cosmetologist. But don’t throw your Driver’s License in a drawer just yet.
What this means for you
First off, California’s pilot program is limited to 1.5 million participants at the moment, and obviously you will need to have an Android or late model Apple smartphone with a functioning digital wallet. Additionally, using Apple or Google’s wallet mobile Driver’s License only grants you the ability to use it to verify your ID at airports, so unless you are a frequent traveler, adding your license to your digital wallet is really more of a novelty at this point. The DMV also has a wallet app that adds a little more functionality: in addition to using it at Airports, the DMV wallet app allows you to verify your age at a select few stores in San Francisco and Los Angeles, and the reader function of the app allows you to verify identification of other DMV wallet users. Not exactly the bold new world you might have originally envisioned.
More importantly, your California mobile Driver’s License cannot currently be used for things like traffic stops or other law enforcement verifications. Some states like Louisiana and Colorado have begun adoption at this level, and as I mentioned above, California intends to expand capabilities of their Digital ID Framework to eventually make your phone a valid ID for this exact purpose. Until this comes to pass, and even when it does arrive, privacy advocates are recommending that you never voluntarily surrender your phone to law enforcement for any reason without a proper search warrant and legal representation. Even the Supreme Court has ruled in this matter. Even if you’ve done nothing wrong and are confident that there is nothing incriminating on your phone, it does not mean the person requesting your phone won’t abuse your privacy or their authority. For now, even if it seems like a very convenient feature, keep your phones in your pocket and your Driver’s License handy.
Image courtesy of Stuart Miles at FreeDigitalPhotos.net