Attorney Daniel J. Siegel's Legal Tech Podcast · 2023-01-13 · 12 min
Key moments - from our scoring
Substance score
23 / 100
Five dimensions, 20 points each
Using outdated software is like eating rotten fish - it may seem fine until it makes you sick. Daniel Siegel draws parallels to real-world failures like Southwest Airlines' technology meltdown to illustrate why keeping hardware and software current is critical for law firms and small businesses. The episode covers the specific risks of end-of-life products: security vulnerabilities when vendors stop issuing patches, compatibility problems with modern systems, loss of vendor support, compliance risks for regulated entities, and performance degradation. Siegel highlights concrete examples including Windows XP (unsupported since 2014 but still in use), Office 2010 and 2016 (which went out of support around 2020), and shockingly, a law firm jerry-rigging systems to run WordPerfect 5.1 for DOS from the 1980s. He references the Center for Internet Security's monthly end-of-support software report as a resource for identifying obsolete products. The takeaway: upgrading requires planning but delivers faster performance, better features, improved client service, and eliminated security exposure.
When a vendor like Microsoft stops supporting software, they no longer issue security patches and updates, making the software far more vulnerable to cyber attacks. Vendors also cannot guarantee that new applications will remain compatible with the outdated software.
Despite being released over 20 years ago and unsupported since around 2014, many organizations still use Windows XP because users won't or can't upgrade, leaving their systems exposed to unpatched security vulnerabilities.
End-of-life software creates security vulnerabilities, compatibility issues that prevent other software upgrades, lack of vendor support, potential compliance violations when handling regulated data, and poor performance compared to modern alternatives.
The Center for Internet Security (CIS) publishes a monthly end-of-support software report that lists products past their useful life, helping organizations identify and locate instances of obsolete products in their systems.
Our reviewer’s read on each dimension, with quotes from the episode.
The episode operates at a surface level with obvious advice (update your software, old software has security risks) repeated throughout without substantive depth. While the Southwest Airlines example and WordPerfect 5.1 anecdote provide some texture, the core message - end-of-life software is bad - lacks novel insights a B2B operator wouldn't already understand. The episode is largely filler around a simple premise.
You wouldn't eat rotten fish, so don't use rotten software
when they don't support their products that means that they are not updating their products to make them safe, secure and to provide the best protection possible
The metaphor of 'rotten fish' is creative packaging, but the underlying content is entirely conventional IT risk messaging that has circulated for years. No contrarian perspectives, no first-principles analysis, and no fresh frameworks - just standard cybersecurity hygiene advice delivered through familiar examples (Windows XP, outdated Office versions). The fish metaphor doesn't substitute for original thinking.
You wouldn't eat rotten fish, so don't use rotten software
Windows XP is a great example of the problem
This is a solo monologue by the host with no guest present. Daniel Siegel is an attorney and legal tech advocate, but there is no relevant practitioner or operator guest to evaluate for caliber or expertise in IT operations.
I am attorney Daniel Siegel and I'm here today to discuss rotten fish
The episode includes some named examples (Southwest Airlines, Windows XP, Office 2010, Office 2016, WordPerfect 5.1) and references specific dates (2014, 1980s, 2020, 2023), but lacks concrete metrics, dollar figures, or detailed case studies. The anecdote about a law firm using WordPerfect 5.1 for DOS is the most specific story but lacks details on impact, costs, or resolution. The Center for Internet Security reference adds credibility but isn't leveraged with actual data.
I work with one law firm who wanted to update their systems and when I talked to them, I knew there were problems. Why? Because one of their users still uses Word Perfect 5.1 for DOS
Many Windows products went out of support in roughly 2020, such as Office 2010 and Office 2016
This is a scripted monologue with no actual conversation, guest interaction, or dialogue. There are no follow-up questions, no pushback, no exploration of nuance, and no genuine inquiry. The structure is purely didactic with rhetorical questions that are answered immediately by the speaker. This format fundamentally lacks the conversational craft dimension.
Hello and welcome to the latest edition of the Legal Tech podcast. I am attorney Daniel Siegel and I'm here today to discuss rotten fish
So why are we talking about raw fish and rotten fish and all those things? Well, let's just look around and look at the news
Computed from the transcript - who did the talking, and the words that came up most.
If you eat food past its expiration date and it has spoiled, you could suffer a fever, chills, stomach cramps, diarrhea, nausea, and vomiting. Or if it is really bad, you could contract E.coli, listeria, or salmonella. Now, imagine if your computer contracted the electronic versions of these conditions and got sick. Computer software also has “use by” dates, commonly known as the end-of-life (EOL) date. These are dates after which a software developer, such as Microsoft or Apple, no longer supports its products. And just like their edible counterparts, using expired software could make your computer sick. In this episode, attorney and technologist Daniel J. Siegel discusses the importance of not using EOL software and outdated hardware, and why it is important to update your software both for efficiency and for cybersecurity protection. The Legal Tech Podcast is sponsored by Integrated Technology Services, LLC and the Law Offices of Daniel J. Siegel, LLC .
Transcribed and scored by The B2B Podcast Index.
Hello and welcome to the latest edition of the Legal Tech podcast. I am attorney Daniel Siegel and I'm here today to discuss rotten fish. Not the type you get in a restaurant, but software. This podcast is sponsored by Integrated Technology Services LLC, which provides workflow, software and other services and training for law firms and small businesses.
And also sponsored by the Law Offices of Daniel J. Siegel LLC in Havertown, Pennsylvania, providing techno-ethical, counsel and other guidance for attorneys and small businesses as well as representing attorneys and individuals in many matters. So why are we talking about raw fish and rotten fish and all those things? Well, let's just look around and look at the news.
Southwest Airlines was grounded. Basically the whole airlines came to a stop suddenly and without any explanation at first. Well, we learned quickly that the primary reason Southwest didn't take off was because it was using outdated technology. And outdated technology meant that when there was a crisis, it couldn't handle the crisis.
We hear about these types of things all the time where someone is using something that is so outdated that it just isn't going to work when stress is put upon it. And that's what I'm really talking about today. You wouldn't eat rotten fish, so don't use rotten software. You know what happens if you eat bad food?
You might get sick, you might get stomach cramps, nausea, vomiting, et cetera. You can get really sick. But now imagine your computer and obviously it's not going to eat bad fish. But it could have old software, software that hasn't been updated.
Software that just like the food on the shelf of a supermarket has passed its use by date. Those dates are the dates for software which the developer could be Microsoft, it could be Apple, it could be Adobe. But it's the date on which they no longer support their products. And when they don't support their products that means that they are not updating their products to make them safe, secure and to provide the best protection possible for you from cyber criminals.
So what I'm here to talk about is computer hardware and software and why you need to keep them updated. Hardware, computer products and computer software were not meant to last forever. In most cases hardware is designed to last a few years. Smartphones, their useful life is really only a couple of years.
And when useful life ends, so does the support. Windows XP is a great example of the problem. People love the product, but when Microsoft stopped issuing updates and patches, the software became far more vulnerable to security threats. In addition, software vendors wouldn't guarantee whether their designed to be compatible applications would continue to be compatible with Windows XP.
But despite the reality, some users wouldn't or couldn't let go and continue to use it. As recently as a year ago, there were a large number of users still using XP, despite the fact that XP was released more than two decades ago and hasn't been supported since about 2014. That's the problem. I work with one law firm who wanted to update their systems and when I talked to them, I knew there were problems.
Why? Because one of their users still uses Word Perfect 5.1 for DOS. I talked about that in my office.
One of my law clerks had never heard of DOS, certainly hadn't used it, and many people still think that Word Perfect doesn't exist anymore. And while WordPress 5.1 was and a great piece of software, you shouldn't be using a software product that was released roughly in the time I got married in the 1980s. But yet this law firm was jerry-rigging its computer so that one of its users could use a product that old.
And while the new versions of Word Perfect remain terrific, using a product that was released in the 1980s is not a good idea. The idea that you don't maintain and that the products don't maintain current versions when they're past their shelf life happens all the time. Many Windows products went out of support in roughly 2020, such as Office 2010 and Office 2016 and other products from that period. So that using scale software is not a good idea and it is time to update.
Plus cybersecurity experts, and this is the advice we give our clients remind clients all the time that they need to update their software all the time. You can't update something that's no longer supported. So it is really important that you look at your computers, consider the software that you are running, and make certain that you are using up to date versions. You regularly apply patches, updates, et cetera, and that you take care of them.
Because when you don't, hackers get involved and they can hack and attack and when they do, they could cause significant damage, prevent you from using your computer, hold you as part of a hostage from ransomware, you name it. So let's talk about some of the security hazards and other issues with end of life software. First of all, it's not going to be compatible. New software products are designed to work better with newer operating systems and other software work perfect for Dos 5.
1, as best as I remember, all installed in one folder, one directory on a computer. That hasn't happened for software in years. Now they're in the Registry, which didn't exist when that product was out and they're used and their files are all over a computer. You may also, by using end of life software, not be able to upgrade other software that you need so that one bed or out of date product could prevent you from keeping your office up to date more.
Another reason is that you don't get support. Who are you going to call for support for Word Perfect Five one for Dos or even Office 2010? And I know firms that are still using Office 2010 and we are in 2023. It's not a good idea.
Plus the new products do more, they do it better, they have a lot of very good features. Then there's compliance issues. If your practice or business includes working with any kind of regulated entities like healthcare providers who deal with sensitive and confidential information, using outdated software could expose you, your clients and others to risks that could endanger the company or lead to fines and other risks. In addition, there are quality issues.
The software that is issued and released today is far better than the software from a few years ago. They have more features, they have better performance, they've fixed issues, they've heard from users and added features, so they're more user friendly. You also could have performance issues. New software and certainly new hardware run far more efficiently.
And when I say efficiently, I mean faster than their older counterparts. Just think about how long it took in the old dial up days just to dial into the internet, whereas now we have expectations that everything is going to happen instantly. The center for Internet Security Cissec Urity.org is a nonprofit organization devoted to safeguarding public and private organizations from cyber threats.
They publish a monthly end of support software report list in recognition that the process of finding end of life dates and locating all the instances of obsolete products can be a difficult and time consuming task. Situations when businesses, law firms and others need to use unsupported or outdated software are for the most part very rare. So that it's not something you need except in exceptional circumstances. In fact, it's time to be looking at your software because if you discover that you have these products, it may be a time to assess what you need, what should be updated, what may be time to end the use of a particular product.
But in summary, end of life hardware and software pose enormous risks for law firms, for individuals, for businesses. But with appropriate planning, you can avoid the dangers of getting sick or rotten fish software. Difficult or not, getting rid of these end of life products should be a priority because your staff will appreciate using newer products, your clients will appreciate the improvement in the service you provide to them and everyone will be happier that things work faster and better.
Thank you. I'm attorney Daniel Siegel. This podcast. The Legal Tech Podcast has been sponsored by Integrated Technology Services, LLC.
You can find us on the web techloyergy.com T-E-C-H-L-A-W-Y-E-R-G-Y dot com and sponsored by the Law Offices of Daniel Siegel LLC and you can find us on the web danieljSiegel.com. D-A-N-I-E-L-J-S-I-E-G-E-L dot com.
Thank you for listening to this edition of the Legal Tech podcast.
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