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I was a developer at Microsoft in the 90s (Visual Studio (Boston) and Windows teams). I won't claim that software back then was "better," but what is definitely true is that we had to think about everything at a much lower level.

For example, you had to know which Win32 functions caused ring-3 -> ring-0 transitions because those transitions could be incredibly costly. You couldn't just "find the right function" and move on. You had to find the right function that wouldn't bring your app (and entire system) to its knees.

I specifically remember hating my life whenever we ran into a KiUserExceptionDispatcher [0] issue, because even something as simple as an exception could kill your app's performance.

Additionally, we didn't get to just patch flaws as they arose. We either had to send out patches on floppy disks, post them to BBSs, or even send them to PC Magazine.

[0]: https://doar-e.github.io/blog/2013/10/12/having-a-look-at-th...

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From the user perspective, Windows and Office certainly crashed more frequently back then. I don't mean that as a criticism of the Microsoft developers at the time: they did some great work within severe constraints. But overall the product quality is far better now.
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I wouldn't take that as criticism; you are 100% correct. But that instability was a direct result of the issues I mentioned above: the ring transition protection/implementation was absolutely horrible; 3rd-party developers would discover a useful function in NTDLL and start using it in unintended ways, etc.

Do you remember the CSRSS Backspace Bug? [0]

A simple: printf("hung up\t\t\b\b\b\b\b\b"); from ring-3 would result in a BSOD. That was a pretty major embarrassment.

After retiring, I started volunteering my time to mentor CS students at two local universities. I work with juniors and seniors who have no idea what "heap memory" is because, for the most part, they don't need to know. For many developers, the web browser is the "operating system".

I absolutely love using Python because I don't have to worry about the details that were major issues back in the 90s. But, at the same time, when I run into an issue, I fully understand what the operating system is doing and can still debug it down to assembly if need be.

[0]: https://jdebp.uk/FGA/csrss-backspace-bug.html

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I can't imagine how much of a breath of fresh air Python / Java must have been if you were used to write typical business crud apps (and server software) in C/C++ (with no sanitizers / modern tooling to speak of).
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It wasn’t. Java was very different from its current state before roughly Java 5. It felt like a downgrade from C++ to me at the time. C++ had templates and RAII and smart pointers, all of which Java lacked (and in some respects still lacks today). Not having something like the C preprocessor was quite annoying. Java performance wasn’t great. Tooling was better in some ways, worse in others. Linters did exist in C/C++, as did debug versions of libraries. You could load a crash dump into a debugger and could often get a pretty good picture of what went wrong. While Java certainly became preferable for business code, it wasn’t a sudden breath of fresh air, it was trade-offs that gradually became more favorable to it over the years.
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I used to joke that using something like Python or C# felt like "programming with oven mitts". I never felt like I had any control. But that eventually morphed into "Well, I don't need that control and can focus on other things."

I spent the last few months building a toy LLM from scratch. I can't believe that within my lifetime I've gone from using punch cards to arguing with Claude when it does something ridiculous.

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The oven mitts metaphor probably works really well, if you shift it into metal working. Yes, it takes getting used to wearing heavy gloves when working. No, you don't want to skip out on them.

Edit: Honestly, any job where gloves are standard works. Gardening. Sailing. Many sports.

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It was the best of times, it was the worst of times.

Best/better because yes, QA actually existed and was important for many companies - QA could "stop ship" before the final master was pressed if they found something (hehe as it was usually games) "game breaking". If you search around on folklore or other historical sites you can find examples of this - and programmers working all night with the shipping manager hovering over them ready to grab the disk/disc and run to the warehouse.

HOWEVER, updates did exist - both because of bugs and features, and because programmers weren't perfect (or weren't spending space-shuttle levels of effort making "perfect code" - and even voyager can get updates iirc). Look at DooM for an example - released on BBS and there are various versions even then, and that's 1994 or so?

But it was the "worst" in that the frameworks and code were simply not as advanced as today - you had to know quite a bit about how everything worked, even as a simple CRUD developer. Lots of protections we take for granted (even in "lower level" languages like C) simply didn't exist. Security issues abounded, but people didn't care much because everything was local (who cares if you can r00t your own box) - and 2000 was where the Internet was really starting to take off and everything was beginning to be "online" and so issues were being found left and right.

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"everything was local"

This was the big thing. There were tons of bugs. Not really bugs but vulnerabilities. Nothing a normal user doing normal things would encounter, but subtle ways the program could be broken. But it didn't matter nearly as much, because every computer was an island, and most people didn't try to break their own computer. If something caused a crash, you just learned "don't do that."

Even so, we did have viruses that were spread by sharing floppy disks.

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That's a really big part of it - bugs were ways that the program wouldn't do what the user wanted - and often workarounds existed (don't do that, it'll crash).

Nowadays those bugs still exist but a vast majority of bugs are security issues - things you have to fix because others will exploit them if you don't.

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There are some rose-colored glasses when people say this.

Programs didn’t auto save and regularly crashed. It was extremely common to hear someone talk about losing hours of work. Computers regularly blue screened at random. Device drivers weren’t isolated from the kernel so you could easily buy a dongle or something that single-handedly destabilized your system. Viruses regularly brought the white-collar economy to its knees. Computer games that were just starting to come online and be collaborative didn’t do any validation of what the client sent it (this is true sometimes now, but it was the rule back then).

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> Viruses regularly brought the white-collar economy to its knees.

Now, it's anti-virus (Crowdstrike) that does that. I don't think many or any virus or ransomware has ever had as big an impact at one time as Crowdstrike did. Maybe the ILOVEYOU worm.

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Saving also often took a long time, so people didn't do it very often.
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Certainly depended on the software. But disks were slow back then, and a save would commonly block the entire UI. If your software produced big files you could wait for an inconvenient amount of time
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It's amazing that the world has largely forgotten the terror of losing entire documents forever. It happened to me. It happened to everyone. And this is the only comment I've seen so far here to even mention this.

Bad old days indeed!

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Indeed, but it was pretty easy to develop the habit of hitting whatever function key was bound to "Save" fairly frequently. I certainly did.

Also auto-save is a mixed bag. With manual save, I was free to start editing a document and then realize I want to save it as something else, or just throw away my changes and start over. With auto-save, I've already modified my original. It took me quite a while to adjust to that.

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If your program's auto-save works like that, it's broken.

Almost none do, though. Auto-save almost always writes to a temporary file, that is erased when you save manually.

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Google Docs and VS Code are the first two that come to mind for autosave and they don't use a temp file.
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Yeah, source code editors tend to do that. They integrate with external tools that expect to read those files, so if they don't overwrite them, those tools would run the wrong version. It would still be better if they didn't.

Text editors shouldn't do that though. And those shared-view editors that don't have the concept of saving have this very relevant drawback.

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Fun fact: I was on the Google Docs team from 2010-2015. Save didn't do anything but we still hooked up an impression to the keystroke to measure how often people tried to save. It was one of the top things people did in the app at first; it was comparable to how often people would bold and unbold text. And then as people gained confidence it went down over time.
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I still occasionally make that auto-save mistake.

AI tools have caused me to trip up a few times too when I fail to notice how many changes haven’t been checked into git, and then the tool obliterates some of its work and a struggle ensues to partially revert (there are ways, both in git and in AI temporary files etc). It’s user error but it is also a new kind of occasional mistake I have to adapt to avoid. As with when auto-save started to become universal.

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> Was software made before 2000 better?

At the time of release, yes. They had to ensure the software worked before printing CDs and floppies. Nowadays they release buggy versions that users essentially test for them.

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Also in terms of security, there was generally a much smaller potential attack surface and those surfaces were harder to reach because we were much less constantly connected.
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> in terms of security

I wouldn't go that far. As soon as you went online all bets were off.

In the 90s we had java applets, then flash, browsers would open local html files and read/write from c:, people were used to exchanging .exe files all the time and they'd open them without scrutiny (or warnings) and so on. It was not a good time for security.

Then dial-up was so finicky that you could literally disconnect someone by sending them a ping packet. Then came winXP, and blaster and its variants and all hell broke loose. Pre SP2 you could install a fresh version of XP and have it pwned inside 10 minutes if it was connected to a network.

Servers weren't any better, ssh exploits were all over the place (even The Matrix featured a real ssh exploit) and so on...

The only difference was that "the scene" was more about the thrill, the boasting, and learning and less about making a buck out of it. You'd see "x was here" or "owned by xxx" in page "defaces", instead of encrypting everything and asking for a reward.

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Software has gotten drastically more secure than it was in 2000. It's hard to comprehend how bad the security picture was in 2000. This very much, extremely includes Linux.
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But there was much less awareness of buffer overflows and none of the countermeasures that are widespread today. It was almost defining of the Win95 era that applications (eg. Word) frequently crashed because of improper and unsafe memory management.
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I remember opening a webpage and being hacked seemed more likely. Adobe Flash and Java had more vulnerabilities and weaker (if any) sandboxes than JavaScript.
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Except that when you did connect Windows to anything it was hacked in less than 30 seconds (the user ignored the "apply these updates first, and then connect ..." advice, they wanted some keyboard driver. Hacked, whoops, gotta waste time doing a wipe and reinstall. This was back when many places had no firewalls). IRIX would fall over and die if you pointed a somewhat aggressive nmap at it, some buggy daemon listening by default on TCP/0, iirc. There was code in ISC DHCPD "windows is buggy, but we work around it with this here kluge..." and etc etc etc etc etc
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Not just dhcpd. Besides the entire existance of Wine and Samba, Qemu has a workaround for win2k. Mkudffs has a workaround for MS-Windows not being able to read the filesystem without an mbr. Libc can work with local system time for those who dual-boot. Git can work around the difference in line endings. There are probably more of these kludges than you can shake a stick at.
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It is hard to say which of the 2 is the reason, more likely both, i.e. lower complexity enabled more exhaustive testing.

In any case some of the software from before 2000 was definitely better than today, i.e. it behaved like being absolutely foolproof, i.e. nothing that you could do could cause any crash or corrupted data or any other kind of unpredictable behavior.

However, the computers to which most people had access at that time had only single-threaded CPUs. Even if you used a preemptive multitasking operating system and a heavily multi-threaded application, executing it on a single-threaded CPU was unlikely to expose subtle bugs due to race conditions, that might have been exposed on a multi-core CPU.

While nowadays there exists no standard operating system that I fully trust to never fail in any circumstance, unlike before 2003, I wonder whether this is caused by a better quality of the older programs or by the fact that it is much harder to implement software concurrency correctly on systems with hardware parallelism.

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The quantity of tests, known as penetration attempts, that most critical software survives today in a networked environment, is magnitudes more daring that the easily-cracked software printed on CDs. I really don't understand how this argument about software made 26 years ago really stands any reasonable ground.
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It feels like rose-tinted glasses. While lots of low-hanging fruit had to be plucked to be shippable, there was still plenty of software which mandated specific hardware/software combinations or (worse) had major bugs which weren't patched but had workarounds documented in the manual, and if you weren't actively reading the manual, your newly-purchased software just wouldn't work (and if it was something low-level, that may mean you have to reinstall the OS).

Then there was stuff like rwall, which could be used to scrawl a message across basically every terminal connected to a networked Unix box in the world by accident [0][1], and it was far from the only insecure-by-design Unix software in widespread use.

It's interesting to watch youtubers like clabretro [2], NCommander [3], and Old Computers Sucked [4] who have documented the slog that was setting up and patching networking equipment, obscure Microsoft products, Netware, Unixes and Unix hardware, old Linux distros, etc. We take so much for granted these days. We don't even have to think about C/++ standards compliance outside the occasional compiler bug, much less the myriad of mutually-incompatible POSIX implementations that helped Microsoft win the Unix wars.

The fact that you can just build a PC with no prior experience or IT knowledge after watching an hour-long youtube video rather than having to spend weeks researching hardware compatibility or futzing about with IRQ levels, recompiling kernels, and messing with autoexec.bat/config.sys is a testament to how far we have come. You don't even have to think about drivers anymore unless you have specialized equipment.

[0]: https://news.ycombinator.com/item?id=31822138

[1]: https://news.ycombinator.com/item?id=35759965

[2]: https://www.youtube.com/@clabretro

[3]: https://www.youtube.com/@NCommander

[4]: https://www.youtube.com/@old-computers-sucked

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Not all software are done with the same quality, whatever the epoch.

It was possible to work with Ada as soon as 1980 wherever high guarantee of reliability was taken seriously, for example.

And not everyone is Knuth with a personal human secretary in well funded world-top institution.

In 2000s, Microsoft which was already sitting on insanely high mountain of resources released Windows Millennium Edition. Ask your greybeard neighbour if you are too young to remember. While commercialisation started in 2000, it is the last MS-DOS-based Windows version and so represent the pinnacle of what Windows 9x represented, before the big switch to a NT inheritance.

As always, the largest advantage of the good all time, is selective memory. After all, people that can remember know they survived the era, while present and future never provided much certainty on that point.

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I’ve been considering that this might be an outcome of AI-written software and it’s the one aspect of all this that I’m actually unequivocally happy about.

Most software written at companies is shit. It’s whatever garbage someone slapped together and barely got working, and then they had to move onto the next thing. We end up squashing a never ending list of bugs because in a time-limited world, new features come first.

But that only really applies when the cost of good software dwarfs that of barely-functioning software. And when the marginal cost of polishing something is barely longer than it took to write it in the first place? There’s no reason not to take a few passes, get all the bugs out, and polish things up. Right now, AI can (and will) write an absolutely exhaustive set of test cases that handles far more than a human would ever have the motivation to write. And it will get better.

If a company can ship quality software in essentially the same time as it can ship garbage, the incentives will change rapidly. At least I hope so.

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It appeared better, because there were fewer features and more time to develop and test. But it's also a lot of nostalgia, because everything moved slower, the world was smaller, there was a lower standard; people will usually remember the later versions of a software, or never even encountered the earlier versions. Without the internet and every one bitching about every little detail, the general awareness was also different, not as toxic as today.
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Just think of 8 and 16 bit video console games. Those cartridges were expensive so just how sure they had to be they were bug free before making millions of them?
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Define better.

Before 2000 fixing a bug the user would notice was expensive - you had to mail them a new disk/cd. As such there was a lot more effort put into testing software to ensure there were no bugs users would notice.

However before 2000 (really 1995) the internet was not a thing for most people. There were a few viruses around, but they had it really hard to propagate (they still managed, but compared to today it was much harder). Nobody worried about someone entering something too long in various fields - it did happen, but if you made your buffers "large" (say 100 bytes) most forms didn't have to worry about checking for overflow because nobody would type that much anyway. Note the assumption that a human was typing things on a keyboard into fields to create the buffer overflow. Thus a large portion of modern attacks weren't an issue - we are much better at checking buffer sizes now than there - they knew back then they should, but often got away with being lazy and not doing it. If a vulnerability exists but is never exploited do you care - thus is today better is debatable.

In the 1990s the US had encryption export laws, if you wanted to protect data often it was impossible. Modern AES didn't even exist until 2001, instead we had DES (when you cared triple DES which was pretty good even by today's standards) - but you were not allowed to use it in a lot of places. I remember the company I worked for at the time developed their own encryption algorithm for export, with the marketing(!) saying something like "We think it is good, but it hasn't been examined near as well as DES so you should only use it if you legally you can't use DES"

As an end user though, software was generally better. They rarely had bugs anyone would notice. This came at the expense of a lot more testing, and features took longer to develop. Even back then it was a known trade off, and some software was known to be better than others because of the effort the company put into making it work before release. High risk software (medical) is still developed with a lot of extra testing and effort today.

As for the second part - software back then was plenty complex. Sure today things are more complex, but I don't think that is the issue. In fact in some ways things were more complex because extra effort was put into optimization (200mhz CPUs were the top end expensive servers, most people only had around 90mhz, and more than one core was something only nerds knew was possible and most of them didn't have it). As such a lot of effort was put into complex algorithms that were faster at the expensive of being hard to maintain. Today we have better optimize rs and faster CPUs so we don't write as much complex code trying to get performance.

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> Was software made before 2000 better?

Literally the moment everyone got on the internet, pretty much every computer program and operating system in the world was besieged by viruses and security flaws, so no.

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Yeah I don't think that is true at all. Plenty of software today is very well tested, and plenty of software back then was pushed out with insufficient testing due to short deadlines (some probably caused by the fact that they had to press CDs).
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It was a simpler time. Not better. Not worse. Programs still had bugs, but they weren't sloppy UI bugs, they were logic bugs and memory leaks. If software was better back then, we'd still be using it!
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Depends what you mean by better. It crashed more and there was a lot of data loss, but it wasn't explicitly evil so maybe on measure it was better.
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Yes and no.

Yes. The incentives for writing reliable, robust code were much higher. The internet existed so you could, in theory, get a patch out for people to download - but a sizeable part of any user base might have limited access, so would require something physical shipped to them (a floppy or CD). Making sure that your code worked and worked well at time of shipping was important. Large corporate customers were not going to appreciate having to distribute an update across their tens of thousands of machines.

No. The world wasn't as connected as it is today, which meant that the attack surface to reasonably consider was much smaller. A lot of the issues that we had back then were due to designs and implementations that assumed a closed system overall - but often allowed very open interoperability between components (programs or machines) within the system. For example, Outlook was automatable, so that it could be part of larger systems and send mail in an automated way. This makes sense within an individual organisation's "system", but isn't wise at a global level. Email worms ran rampant until Microsoft was forced to reduce that functionality via patches, which were costly for their customers to apply. It damaged their reputation considerably.

An extreme version of this was openness was SQL Slammer - a worm which attacked SQL Servers and development machines. Imagine that - enough organisations had their SQL Servers or developer machines directly accessible that an actual worm could thrive on a relational database system. Which is mindboggling to think about these days, but it really happened - see https://en.wikipedia.org/wiki/SQL_Slammer for details.

I wouldn't say that the evidence points to software being better in the way that we would think of "better" today. I'd say that the environment it had to exist in was simpler, and that the costs of shipping & updating were higher - so it made more sense to spend time creating robust software. Also nobody was thinking about the possible misuse or abuse of their software except in very limited ways. These days we have to protect against much more ingenious use & abuse of programs.

Furthermore today patching is quick and easy (by historical comparison), and a company might even be offering its own hosted solution, which makes the cost of patching very low for them. In such an environment it can seem more reasonable to focus on shipping features quickly over shipping robust code slowly. I'd argue that's a mistake, but a lot of software development managers disagree with me, and their pay packet often depends on that view, so they're not going to change their minds any time soon.

In a way this is best viewed as the third age of computing. The first was the mainframe age - centralised computer usage, with controlled access and oversight, so mistakes were costly but could be quickly recovered from. The second was the desktop PC age - distributed computer usage, with less access control, so mistakes were often less costly but recovering from them was potentially very expensive. The third is the cloud & device age, with a mix of centralised and distributed computer use, a mix of access control, and potentially much lower costs of recovery. In this third age if you make the wrong decisions on what to prioritise (robustness vs speed of shipping), it can be the worst of both the previous ages. But it doesn't have to be.

I hope that makes sense, and is a useful perspective for you.

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I think there was a period where things got better but I don’t think it was pre-internet.

There was a point in time where both windows wasn’t constantly bsoding and Microsoft’s primary objectives weren't telemetry and slop coding.

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Delta, JetBlue, American Airlines and Alaska Airlines have free Internet as long as you are enrolled (for free) in their loyalty programs.

JetBlue and Delta use ViaSat. I only fly Delta for the most part and ViaSat was available on all domestic routes I’ve flown except for the smaller A900 that I take from ATL to Southwest GA (50 minute flight). Then I use my free unlimited 1 hour access through T-Mobile with GoGo ground based service.

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