REVIEW: Top 50 Worst Computer Dialogs by a Microsoft UI Developer!

[@araghon007]

I was hoping these would be actual dialogs, but oh well. If it were, the WinForms FolderBrowserDialog would definitely be in the top 5

[@JustARegularNerd]

Yes! It would’ve been good back in the Windows 95 days where screen space was limited and having a compact design made sense. But when you have anything higher than 1366x768 that dialog is the bane of everyone’s existence.

[@BrianB14471]

Agree. I was expecting real Windows dialogs. Not contrived examples as these obviously were.

[@jwhite5008]

Agreed. Most infuriatingly, the is editbox is optional, and disabled by default. So even if you already have a path in your clipboard, NOPE!, you have to enter it manually. Especially fun if you have more than 100 subfolders By the way, gnome (linux) devs that removed editbox from "open" dialog shall burn in hell.

[@MrTridac]

Oh yes! The folder browser is sooo bad. I bet it was Bill Gates idea, and nobody had the courage to tell him that it's completely unusable.

[@IgnoreSolutions]

Ew, I remember that. I remember using that class thinking it would be a traditional open-file dialog configured for folders only. ***Nope***. Instant regret.

[@bitpickersplace494]

One of the strangest error dialog boxes I’ve ever seen was the with the message, “An unknown error has occurred.” I’ve always felt that there was enough information to really say something about what had just happened. Something was known.

[@xXYourShadowDaniXx]

They at LEAST had to know where (function) it came from because everything has stack traces for decades

[@oddvertex]

No keyboard detected … press 1 to continue

[@llothar68]

As a programmer i'm guilty of this. Even worse, the coding style calls for a desciption of the operation when the error occurred so i wrote a message: An unknown error has occurred while doing something.

[@jonwallace6204]

This usually occurs when you’ve correctly caught an error, but while trying to get information about the error, you get another error or no error info. Usually when communicating with another process, such as a database. Personally, I’d still specify “unknown database error” but a lot of dialogs are really only meant to be seen by the dev and just wasn’t put in an ASSERT for some coding standard. Also in some error cases, you don’t want to dynamically create a new error string, such as when out of memory. There is usually a universal catch with a static error option in an attempt to tell you something before a crash.

[@Kreze202]

As a dev, I can tell you that we can't anticipate literally every single thing that could go wrong in a system. Yes, there are logs that you can analyze after the error happened, but a generic "unknown error" message is most likely an actual "unknown" error that the devs didn't anticipate when developing the system.

[@DavidWonn]

I thought for sure there’d be a reference to the old "illegal operation" errors in the Windows 95 days, complete with that very harsh error sound effect. There are legends of stories of users taking it so literally that they thought the police were about to show up!

[@camthesaxman3387]

Ooh, yeah, I hate when programs use the word "illegal". I normally use "invalid" instead.

[@joemck85]

@@camthesaxman3387 Then you get irate users calling and screaming "the computer called me an invalid".

[@geb2]

AND MUST BE TERMINATED

[@mrtechie6810]

@@camthesaxman3387 that would be ableism though

[@LARathbone]

The DOS "Abort/Retry/Fail" prompt literally scared me as a child, as did the Windows 3.x Close/Ignore General Protection Fault dialog

[@BrianWanda]

Programming in the 90's was a blast. No one knew what it should look like.

[@seankkg]

And now we've spun back around to nobody knowing because the developers insist we want it their way when modern UI is always really unfortunate and we do not want it their way.

[@sirflimflam]

I got in at the late 90s, but even then it felt like the wild west. If my younger self knew what we were capable of now, he'd freak the ever living shit out.

[@johnathanstevens8436]

Yes, and just when I was starting to get nostalgic for VGA MS came out with Windows 8. "We blew millions of dollars on Windows Phone, what do we do? I know, we'll adapt the interface to desktop PCs that only have a keyboard and mouse!" Instructions to grandma: "Just bang the mouse around the corners of the screen and start right clicking on everything.. Press CTRL-P to print."

[@RedShift5]

Actually that's not true, both Microsoft and Apple had user interface guidelines, it was well known how to design user interfaces. In fact a lot of research work went into the Windows 95 user interface.

[@BrianWanda]

@@RedShift5 Our requirements came down from a guy with a file cabinet, electric typewriter, and an ash tray in his office. He'd look over at a stack of punch cards and back at us and say "not that way, whatever you do". Users would whine less if you stuck a pin in their eye vs having something that required a double-click.

[@AndreasToth]

Talking about bad dialogs, mobile user interfaces are full of them, especially when it comes to drop-downs or any graphical control dealing with lists of items where the user is expected to select one or more items. Under a desktop system, such as Windows, the user can use the keyboard to type the first letter, or on a well-designed control, letters to quickly jump to a specific entry. Most mobile user interfaces controls for similar lists don't provide any means to quickly locate specific items, something that would be really simple to do by displaying a search field where the user could optionally type. But oh, no, instead we are back in the dark ages and have to manually hunt for the required item or items!

[@greggv8]

That's what I really liked on Android phones with real keyboards. Hit the first letter to go to the part of the dropdown with options starting with that letter. But then it got better. Hit the second letter of what you're looking for and it would go to the first one containing that as the *second* letter. So if you needed to select from a list of sports you'd hit B to go to sports starting with B, then I, then C and almost certainly you'd be on Bicycling. Windows... does not work that way. Nor does Android with a touch screen as its only user input. There is one company about to release a high end cellphone with a 5 row slide out horizontal keyboard - but it has those completely stupid curved edges on the display.

[@lucidmoses]

You could make an episode like this with real dialog boxes for windows, ios, linux, etc. I'm sure if you asked your patrons(or everyone) would send you a flood of them.

[@user-sl6gn1ss8p]

granted it had bugged, but my printer once sent me a dialog which had no text other then "warning" on the title and the only option was "yes". Pretty ominous, coming from a printer.

[@beest_]

Yeah agreed. I once had seen example of bad Dialogs and I jumped at the chance to see Dave's list.

[@lucidmoses]

@@user-sl6gn1ss8p Yeah, there has been a ton of them over the years.

[@Elesario]

Here's a starter, the Evaluate Formula dialog in Excel. It hasn't changed since at least Excel 2003. Try debugging an array formula in it to see how bad it really is.

[@mfThump]

@@user-sl6gn1ss8p hoping that you know about the windows + printer vulnerability/exploit (s)

[@WaynesWorld999]

Several years ago I got a dialog box that said something like this "Windows Update needs to update Windows Update before Windows Update can update Windows." I wish O took a photo of it haha.

[@nickwallette6201]

Every single update on Office 2016 for Mac. Apparently, they never actually got the Updater right because _not one single time_ would it just carry on updating the Office apps. No, first I had to update the updater, _then_ I could download my 1.3GB "patch" to Word. Ugh. Whatever the opposite is of employee of the month, the Office team deserves it.

[@RonJohn63]

Did it make you cancel and then update Windows Update, or was it just informational?

[@frankhaugen]

"Error - No error found" was something I managed to see multiple times a week when I was running Win98se or Win2k (very early two-thousands anyway). Ot drove me nuts. I usually got it when a game crashed, (Red Alert and Settlers 2 particularly). I was just a child back then so I didn't know to look at logs, but the error message stuck with me for a long time. I had suppressed that memory, now I'll be having flashbacks for days 🤣

[@PartTimeLaowai]

Reminds me of a Windows Media Player dialog I got years ago (and screen-capped lest noone believe me) "Error 0 the operation completed successfully"

[@staceyward777]

I'm still running Win2k and I've never seen that. Ever.

[@frankhaugen]

@@staceyward777 I can speculate that opcodes probably is the culprit, and so the application calls "application error" without populating the correct queue, and this is more likely when Windows is localized, (I had Norwegian windows), so the error message isn't found for the message box and so the error text of that lookup failure is presented. I could check the leaked source code but I'm too lazy for that

[@dvongrad]

Taking away things in Windows 11 for simplification like not being able to move the taskbar to other screen edges or not adding tollbars to it is the same as stupid dialogs in my books.

[@benjaminschwartz7616]

Worse, even! We all know how to use things just fine and then they change it all. And the "simplification" doesn't even it make it easier for new users.

[@littleloner1159]

They did what??? I've been using Linux all my life, and so last week I decided to try windows in a VM .... If they wanna simplify stuff they should start with the lengthy installation process, the mirage of advertisements and the unbelievable bulk of the whole system Oh and how to get to things, seems like everything requires at least 5 clicks to get to. I don't think anyone needed even less customisation options.

[@lucasgroves137]

After "up"grading to Windows 11, I rolled back to Windows 10 so fast I almost cut myself.

[@criptych]

Switched my laptop to Linux years ago, kept my desktop on Windows 10 for gaming, but I've already decided I'll switch completely to Linux before I let Windows 11 on any of my personal machines.

[@notarabbit1752]

My favorite is still the more recent Windows dialog: "Something Happened: something happened"

[@AusSkiller]

You were responsible for task manager UI? Wow, great work, I really liked the task manager UI, it has what I need where I need it, it doesn't waste space, and it is reasonably responsive for what it displays. Over the years I've held it up as the example that Microsoft can do better every time I encountered all the terrible UI Microsoft has been adding over the years. The other dialog I loved was the old Windows 95/98 file search dialog it did everything I wanted and always seemed to work so much faster and more reliably than the Windows XP and later file searches which more often than not don't ever find the file I'm looking for.

[@davelloyd-]

I've always hated the change from find to search. I can't get past 'I want to find stuff, not keep searching for it!' It's a nuance that always bugs me. But yes, I also concur - despite adding indexes etc to speed up 'search', it seems we lost some simple basics versus the olden days. Top tip; drop to command line and use dir or something :)

[@danielscott4514]

@@davelloyd- top tip in the windows search era is to start your search for part of a filename with name: (name colon) - that stops windows search looking inside files for whatever search term follows.

[@nakfan]

@danielscott4514 Thanks. Will remember that one…

[@PyroX792]

While I agree you handled the situation poorly I do think you were correct in thinking functionality shouldn't be sacrificed for "simplification". There are lots of great ways to increase usability, keeping an interface clean and simple for new or average users, without cutting off access to functionality that would be useful to a more advanced user. It troubles me that functionality gets removed completely in misguided attempts to make something better for new or more casual users. It doesn't have to be that way. IMO it is lazy to just delete functionality instead of designing a good UI. That's just my 2 cents. I'm not UI designer myself.

[@ColinTimmins]

I agree, I HATE when things get "simplified" and it ends up getting rid of functionality. Just because someone thinks others can't handle it, don't make others suffer because of it. I'm glad he put up a good fight, and even gladder it didn't cause him his job... lol

[@KristopherNoronha]

completely agree. I'm saddened whem Microsoft goes down that route repeatedly. One of the reasons I miss Windows XP, which IMO was peak Microsoft.

[@knyshov]

“The web has now democratized access to bad decisions for everyone” - I love this. :)

[@MauricioRPP1]

Best line!

[@thextremeking]

"Can not delete file, disk full" (or something very similar) is one that comes to mind when thinking about bad dialog popups. I don't know which windows version it was anymore.

[@nickbooker5579]

Keyboard error, press F1 to continue

[@RonnyJakobsson]

It was and still is MacOS.

[@Mavendow]

​@@nickbooker5579 Keyboard Error Press F1 to Continue, F2 to Retry I've actually gotten this error. It makes more sense than you might expect at first glance. See, the PS/2 port was tied to hardware interrupts, so if it failed, your computer would not boot. If your keyboard was faulty or not connected it likewise would prevent booting because of this interrupt problem. So, if you could press either key it meant the system was not registering the keyboard correctly. Say, you accidentally pressed several keys and triggered the error, but it wasn't an actual hardware fault. In the modern days many people no longer understand why this error existed.

[@hquest]

"Can't write, disk full" is the message.

[@nickbooker5579]

@@Mavendow ah ok I stand corrected, thanks for pointing out a genuine use case. I and my friends only ever got it when the keyboard was disconnected which is why it seemed daft at the time. As I became a more experienced developer I took it as virtuously lazy programming and the joke being on the apparent non-sequiteur rather than the UI design itself.

[@BenChilds]

Next do Active Directory Users and Computers for a real horror show. nothing resizable, control frames that aren't anywhere near the size they need to show the most basic of data, no easy way to copy data into or out of it. Unlike these hypothetical novelty volume controls, this is a real production tool that many people use multiple times per day and likely wouldn't pass even Windows 95 design standards muster. We shouldn't have to resort to using powershell to get at things because the basic user interface has been stuck in the same sorry state since inception.

[@gruntaxeman3740]

IIS was also horror to configure. That fancy GUI was just terrible compared to Apache HTTP and edit simple configuration file (that has help in commentlines) using nano or something. I do like to use GUI on many things but it can also backfire heavily.

[@mpdavis731]

Maybe one about best error messages? My favorite error message: "gdm tried to start, but was murdered mysteriously" - got this back in the old days of XFree86 manual config when I had a borked config. Second would be the time a panicked architect ran over to my desk and asked what it means when the command line says "I have no name!" when logged in as root - I was a new hire, and he was the CTO's brother, and lead enterprise architect - I told him either glibc was borked, or etc passwd was borked - turns out the sysadmin manually edited the passwd file - the kicker was it was when adding MY user name - which he messed up by giving me a user ID already in use . Thanks for the videos, always entertaining!

[@chrissimpson1183]

I love the error message "Windows Task Manager has stopped working". I always say you are the chosen one, you are here to end them not join them!

[@BenState]

I thought this would be all the horrible windows ones, but the last one is totally in my memory!! thanks Dave

[@piratk]

Since a long time ago, I hate all dialogs that question me, with "are you sure?", especially those that don't protect anything non-revocable.

[@russlehman2070]

I definitely agree. Ask me if I'm sure if I'm about to format my hard drive. Otherwise, please assume I know what I'm doing.

[@pantherosgaming1995]

Great job on that task manager, the design team has really evolved your design of it to levels of usability and information that really keeps me looking at it when I have issues.

[@lawrencemiller3829]

I wrote a list of ~30 rules for a GUI to document my manager's requests and my ideas of industrial art. One came from the customer, don't be overly colorful or drab. One of mine is, fields should be in reading order as used, for the US, that is left-right, top-bottom. An issue was another developer using square boxes as radio buttons and circles as checkboxes. (Do it the other way round like most GUI's!) The new CEO recommended the book "About Face 3" to us.

[@pharoah327]

I HATE it when radio buttons are portrayed as boxes. This screams of ignorance and blatant disregard of good user interface. Many Flash based websites were guilty of this. Glad we don't have to deal with that anymore.

[@Dream.of.Endless]

The closest I had come to that retry dialog, was with floppies, but someone had the insight to add 2 more options, fail and abort.

[@Dee_Just_Dee]

I remember that one! I was just a child using hand-me-down computers in the MS-DOS 3.x era, and of course the Web didn't exist yet, so it was years before I finally got to know what the difference between Fail and Abort was.

[@jacoblf]

With no description of what the difference between Fail & Abort was!

[@fleshTH]

Holy crap... As soon as you showed that retry dialog I had flash backs. I've seen that many, many times and was always very frustrated with it. I remember as a 12-13 year old yelling at my computer "why can't I abort?" and angrily holding down the "R" key for several seconds as if that was going to teach it a lesson.

[@liesdamnlies3372]

And now you know to to blame (or put a hit out on, depending on just how traumatizing the experience was).

[@SteveJones172pilot]

One reason I NEVER installed software like that.. I never trusted any add-on compression or caching software I had the option to NOT install (No offense Dave.. it was mostly because I had cheap hardware and no battery backup!!!)

[@blahorgaslisk7763]

I worked with MS DOS from version 1. something, and I'm happy to be able to say that I didn't know that dialog even existed. I thought the old "Not ready reading drive, Abort, Retry Ignore?" dialog was the worst one...

[@russlehman2070]

There was also a similar one, "General failure reading drive C:" (or A: or whatever). Which raised the question, "Who is General Failure, and why is he reading my drive?"

[@wchen2340]

Major Update told you not to turn off the computer. Thats why^@@russlehman2070

[@adrianstephens56]

I love the kind of dialog (can't remember exactly what issued it) that says "something went wrong. We've lost all your data." with a single "OK" button. No, it is definitely not OK.

[@DavesGarage]

I like them even better when the error is "The Operation Completed Successfully" and you get an error for S_FALSE@!

[@nochan99]

Bro, both the 7-segment display and the double click features are what made it cool.

[@nEuDyYT]

Remembers me to a nowadays Windows10/11 UI dialog, when you are trying to remove a device in the new control panel for devices and click "Remove device". The only option you have for the messagebox "Are you sure?", is a "Yes" button.. nothing else 😅

[@PartTimeLaowai]

Reminds me of a Windows Media Player message I got years ago (and screen-capped lest noone believe me) "Error 0 the operation completed successfully"

[@Dee_Just_Dee]

I let those ones slide. Dialogs like that typically have a X button which is an implicit "Cancel".

[@nickwallette6201]

@@PartTimeLaowai Yeah, that one's funny, but there's actually a good reason for it. Errors are (I think on Windows, but at least on Linux) an integer value, with 0 being the code for 'no error occurred,' ergo "The operation completed successfully." So when you get informed of this result as if it were an error, it's because somebody forgot to special-case the 0 return value (or maybe expected a non-zero result with errors being negative values), and also called the system function to get a localized string description for a given numeric error code, which was 0, and hence the "All went well" 'error.'

Thanks, this was fun! Have you heard about the Interface Hall of Shame? It's a treasure trove of real vintage GUI designs that make you shudder. I'd love to hear your thoughts if you decide to explore this topic further :)

[@llothar68]

Unfortunately i looks like nobody entered something new the last 22 years. The webpage is now a shame on itself.

[@jeffreyphipps1507]

Removing functionality: like removing the controls for bass/treble in W10, removing the ability to put the taskbar any place you want/need in W11. I hear you...

[@KristopherNoronha]

no balance controls from windows 7 onwards. only noticed that when one channel of my amp blew and I was trying to troubleshoot it!

[@roycsinclair]

The number one worst interface is also one of the most common interfaces. When creating or updating a password the RULES to be followed are not available until AFTER you've entered a password. It should in fact be a test for whether a person should be allowed to create any interface, if they can't see the utility of making the rules known up front then they have no clue whatsoever about what makes a good interface.

[@patbanglephoto]

Perhaps this is done to make it slightly more difficult for would-be brute force hackers to easily scrape the rules and narrow down their attack dictionary. It might not really help, but from a security standpoint it makes sense.

[@roycsinclair]

@@patbanglephoto Nope, it's a design defect pure and simple. Since you can get the rules with the first try there's absolutely no benefit for security.

[@patbanglephoto]

@@roycsinclair If you don't see the difference between having the rules statically available (and therefore scrapable with zero interaction) versus having them obscured behind some code and only visible with a little added friction, then I can't help you.

[@roycsinclair]

​@@patbanglephoto Obviously you've never held a job where data security was one of your jobs.

[@roycsinclair]

@@patbanglephoto You are essentially arguing for a tiny bit of "security by obscurity" which is a FAILED concept. It is NO trouble at all for a hacker to find those password rules AND brute force hacking is only useful these days when you have password hashes you're trying to match, that will only occur long after you've already found those password rules. You seem to be arguing like this is some sort of thing you have done yourself and you're trying to justify having done it This is NOT an interface error I have made, my worst personal offense was rearranging the fields on a form to a more natural and sensible order but the primary users of that form were data entry operators entering the data from a paper form and the form was originally in the same order as the paper form but by reordering the input form I made the data entry much harder. They made it clear the first time I showed them the new form that it had to be fixed.

[@PartTimeLaowai]

How about that nastiness being the Windows 10 change date/time dialog? It was so simple and clean with Windows 7 - minimal pointing, clicking, and/or typing of numbers to get the job done. In a case of seemingly "let's change something for the sake of change", Windows 10 requires more mouse clicks and scrolling through drop-down listboxes (which on my 15.6 inch laptop won't even show the full day-of-month list at one time)

[@kirktown2046]

How true, I'd forgotten how clunky it became.

[@Alexagrigorieff]

Windows 7 was the pinnacle of MS UI. It all went downhill with Windows 8.

[@Dee_Just_Dee]

I think _in general_ Windows 10 is pretty bad when it comes to changing any settings at all. You never know if the setting you want to change can be found in a classic Windows dialog, or if you'll have to open one of those Windows 10 style dialogs. And even so, there's plenty more of that "change something for the sake of change" you mention.

[@Devire666]

I've used the English version of Windows 10 for the first time a couple of years. And was surprised how painful it is to set the European style date/time format but the American keyboard layout. Cause it makes sense that to use a format you have to install the appropriate keyboard layout, right? Want to use the British date/time format? You'll have to have the UK keyboard layout on top of the US layout. And if you uninstall it, then the date/time formant will revert to the US one. Makes total sense. And then, it turns out that the Control Panel has a totally separate range of options for the date/time setting. Which allow you to set the date/time format by yourself. And I still could not make the date look exactly how I wanted. Cause instead of having separate settings for the day/month/year order and the dividing symbol ("/" or "-") you can only choose from the predetermined options.

[@user2C47]

@@Devire666 Won't work on 11, but you can set a custom clock format with a utility called T-Clock.

[@jpjokela1]

The worst EVER windows dialog has to be the Windows 10 upgrade dialog. It would pop up, and ask if you would want to upgrade your computers OS to Windows 10. Below that were 2 buttons, Ok and Cancel. If you do NOT want to upgrade, just press Canc... NO! That actually makes the system download the upgrade in the background, and force installs the next time you reboot your computer! The ONLY way to cancel was actually to just close the window. (Ok starts immediate install - THAT does what everyone expects) Not sure if it was that same exact requester, but if you failed to react in time (if you were playing a game or something, it would also force install.

[@Rx7man]

While not a dialog box, I think one that's WAY up there on bad UI decisions in MS was with the "task ribbon"on what think was Office XP... Just at the time when widescreen monitors gained popularity, which also meant that vertical real estate was at a premium, they add a nice fat 100 pixel task ribbon on top, along with fatter borders which made your effective vertical viewing about 15 rows in Excel. Facebook suffers from this, as well as other sites.. Widescreen monitors in landscape mode, and most portable devices viewed in portrait mode means you can't design something that'll just work nicely for both

[@BenChilds]

MS teams behaves very badly on portrait oriented monitors. You can't resize the separation pane between chat channels and chat text.

[@BoraHorzaGobuchul]

I personally find the ribbon much better than the old-school toolbar. What is bad is that it wasn't customizable at first, and isn't very customizable now. To truly customize it one has to use specialized tools and dive into the syntax and spend lots of time doing this, then have to do it again every time you decide to modify your ribbon. This truly sucks since a simple built-in gui ribbon editor would save so much time and effort. Of course, I understand the logic "nobody customizes their toolbars/ribbons anyway so why bother".

[@russlehman2070]

I think Office peaked at something around Office 97. Until then, they kept the interface pretty consistent. It wasn't the best user interface ever devise, but it was decent, they kept it pretty consistent from one version to the next, and I knew where everything was. After that, they started making it gimicky and fell into the "change for the sake of change" trap, so you had to learn a new user interface with every new version.

[@MisakaMikotoDesu]

I want to see all the ancient 3.1 dialogs that still exist in Windows and have you explain them why they're bad! Please do a follow up with this, it'll be a hit!

[@rick_.]

"Interface Hall of Shame" has a good selection of UX fails from days gone by. It's long gone, but Google will yield some archived copies.

[@arjanvuik2004]

I had this dialog show up once on my computer! I opened my harddrive to see how it works(I was 12~13 I think) And to see the funny arm go up and down I started a scandisk. In my memory, I got this error... It is save to say that this harddrive never recovered, to my dad's horror :D

[@davidshoemaker1056]

Long long ago, I worked on dBase development and the color's for strigs in the UI were determined by character codes, a coworker of mine was blind and would pick his colors by randomly hitting the keyboard and then saying "Hey David, how's this look?" I would then be subjected to flashing red / yellow text over blue/ green backgrounds.

[@jacoblf]

Hey Dave! Is there any way I can get dBase working on MacOS?

[@martsmiscmix]

The Christmas card comment from your daughter had me in stitches - she sure "gets" you! - well done her!

[@Tahgtahv]

tho it actually says Merry Ahristmas (but what's a 1 bit error between family)

[@bigsky1970]

One of my favorite error messages going back to the MS-DOS days was when the computer was booting up and if the keyboard wasn't connected to the computer, MS-DOS would throw out the error, "Keyboard Missing Error: Press F1 to continue". It had only happened to me once or twice, only because I was moving things around in my computer lab and the keyboard connector pulled out enough from the keyboar socket that it wasn't making a proper connection. So, whoever coded that into MS-DOS back in the day, certainly had a sense of humor.

[@justsomeperson5110]

Heh heh. Reminds me of the old days where I aaaaaalmost got into a LOT of trouble for one of my poor young choices in a user interface, the "Stupid User Error". Yes. It was that simple, an error message dialog with that title. To be fair, the ONLY way to get the "Stupid User Error" message was if a user hand-edited a tab-delineated data file using *spaces* instead of tabs. Further, it was a file generated by machine and was in no way human readable. However, that did not stop some "experts" from trying to "fix" data that they considered "wrong", and to do so using the wrong separation character. As deserved as the "Stupid User Error" may be, calling self-important customers who think they're all that what they are does not win hearts and minds ... or sales.

[@whkiess]

Yes, that brings to mind the users I worked for who had a habit of editing fixed record length text files and CSV files using word processors and wondering why they files didn't work anymore after their handiwork...I added a dialog box like that, did it to make me feel better, but then erased it again to remain "professional". At least one of us had to be.

[@JohnSmith-qy1wm]

Screwing up the delimiter (via the creator or receiver/user) is actually very common, especially with data from old (long-maintained) systems.

[@anthonycokayne7453]

I like the volume matching idea! Instead of saying "alexa, volume down" 5 times in a row, just say "alexa, match my volume"

[@joedeshon]

0:47 There has never been a UI as beautiful and as perfect as Windows XP. Buttons looked and felt like buttons; you knew exactly where you were supposed to click and exactly what would happen if you did. The title bar, screen edges, and scroll bars were things you could literally latch on to. They were loyal, reliable friends that you could count on to always be there and perform exactly as you commanded them to do. Nothing was metro, washed-out, or ambiguous. Menu items dropped down as expected and displayed exactly what you were looking for. In their effort to make everything look consistent, Microsoft has made the Windows UI mushy, icky, and downright confusing. Buttons don’t exist, just icons that change size and shape at will. You never know what’s lurking under a menu item. Title bars are who-knows-what color -- and oddly, translucent because somebody thought that would be a good idea (?!). Good luck clicking on them, if you can even find them. Who knows what window has focus? I have no clue. Words that appear seemingly randomly-placed on the screen may or may not be clickable. And who knows what will happen after you click them? And the most touted feature of Windows 11? Icons on the Tasks Bar are now not left-justified, they are centered! Big Whoop! I wish there was a Windows option to make the UI look like XP. I stay up late at night longing for the good old days of 2001!

[@CubicApocalypse128]

If you ask me, the last version of Windows with *good* UI was 7. There will never be another.

[@miss_sapphire]

Loved xp but windows 7 quickly grew to be my fave. Loved all the little gadgets and aero

[@miss_sapphire]

Xp was great though using vbs to make magic merlin float around the screen lol

[@mikem6549]

Hats off to Lloyd's bank, millenial programmer and google/android who made my dad's proxy(me) press the down arrow 85 times to select the year of his birth.

[@nickbooker5579]

Oh those rolling date and time entry things are a PITA. Just let me type the digits in each field.

[@PhilHibbs]

Worst dialog I ever saw was a super early version of Microsoft Antivirus: “The diskette in Drive A contains a boot sector virus. You should reboot this computer immediately.”

[@Jenonator]

I have too say, I'm really impressed by your call to action. They fit so well in the videos and keep the same passing and communication level! I just now realized, that I never really get annoyed by them 😄

[@salkabalani1482]

Your videos are usually amusing and informative. This one is gut-busting laugh out loud funny.

[@davepickering997]

Great video Dave, I was giggling to myself watching on silent with the CC on (as I am in a bar overlooking the Indian Ocean)

[@MrGeocym]

Only recently discovered your channel Dave but gotta say everything i've seen so far is gold. your videos are immensely watchable and i hope there are many more to come

[@FalconFour]

Oh man. I REALLY wished this were an episode of real dialogs, not contest entries for "making the worst phone dialer or volume slider you can". Ended up skipping to the end to see the only real dialog and wasn't disappointed! I totally understand that decision and there's no better way to handle it at the time. Today though, you just get the "delayed write failed" subtle little notification bubble in Windows that just kinda ~by the way~ notifies you then leaves 😂 anyway yeah, would be amazing to see a compilation of real examples 🙃

[@nickwallette6201]

Oh man, that "delayed write failed" thing... I mean, you could at least tell me what data I just lost. Instead it's just kinda like, "Oh hey, some day you're going to open a file and expect your stuff to be there, and I'm just letting you know it won't be. Kthxbye."

[@nickbooker5579]

Digital microwave ovens, especially those designed like there's a tax on buttons, or use rotary encoders with time increments that change on an arbitrary half-past-the-minute. Numeric keypads allowed me to enter any time I wanted in at most 4 button presses (usually 2 or 3), but that's so 1990s.

[@MichaelEllsworth]

I have had that dialog save my bacon, because the end user did something to the system and unplugged the SCSI adapter they called me to fix it rather than losing the very important report for the state they had spent nearly 2 weeks on without saving. Yes, it was 2002, and the computers were still running DOS, and they lucked out that power didn’t fail.

[@douro20]

I hate over-simplification. It is something which seems to plague modern OS design, especially on the Windows side. Sometimes you'll find non-English error messages in software which was otherwise written in English. For instance, I remember a piece of Windows 3.1 software which once displayed 'Nicht genügend Speicher' (not enough memory) when I once tried to open it.

[@antisoda]

Non-English error messages turn me to drink. Especially when I need to Google it to find a solution, and of course, there's not a single result. Then having to rack my brain trying to deduce what the English error message originally could be. Argh…

[@Gunbudder]

9:05 I HAVE SEEN THIS. I immediately tried to refactor it with a number updown and some validation code to fix the range, and my changes FAILED REVIEW. The reason? The ganged radio buttons have "better user input validation" and were "easier for the tech to use." My next thought was that i wanted to create a peripheral that allowed the user to select options by fitting various shapes through shaped holes, or maybe shake a rattle a certain number of times.

[@opensage01]

This made me laugh more than most comedians these days haha. Some of those are just pure gold. Thanks for posting and cheers.

[@georgeprout42]

There is a subreddit for these sort of things, often with source code r/badUIbattles

[@joko7456]

I can make that last dialog worst with two buttons. Press R to retry or R to restart. What you get is.... well depends on the bugs for your platform.

[@jackgerberuae]

That’s evil 🤣

[@lightningdemolition1964]

How about R to retry or r to restart

[@tm36105]

Hey Dave, I watched tons of your videos because of the same scenario you described at 5:02, in fact i'm here on a year old video just for that reason. Thanks for your description and not just saying "Smash that like button and make sure you subscribe". Your videos are all very well articulated and great history for us who came after you supporting the systems you helped create. Subscribed.

[@jopgaard]

I love hearing the history from Microsoft from someone who was there. I wanted to ask if you ever went to the library on the Microsoft campus. For several years they ran their library management system on OS/2 workstations. I know this because I worked with that library management system at a library in Tacoma and visited the Microsoft library to see how they operated. It was interesting the collection of software that they had in the back on compact shelving in the original boxes. The days before you downloaded everything. This would have been in about 1992.

[@MickeyMousePark]

My favorite: New Unknown device found Loading Unknown Driver Successfully loaded Unknown Driver Unknown Device is ready for use..

[@ufoisback5088]

Task manager was my favorite in the XP. I now realize years later that this is cuz it was designed by a developer. I loved those load charts. Obviously, windows would've never had this. Ofc... Now we know.

[@Lirchicus]

I have always taken great pains to design good user interfaces (even reviewing them with the end user), so this put a huge smile on my face! Thanks Dave!

[@joer8854]

I actually got an enter birthdate interface with the + key once and realized in horror there was no way to select the year or month separately. Personally I don't need to be reminded of precisely how many days have passed since I was born.

[@davidlean8674]

Australia's emergency number is 000. It started in the era of rotary dial because there was no way you could accidentally dial 0. MSFT continued your infamous Retry UI into Windows with the "I'm going to kill your kids, sleep with your wife & peel your skin off with a can-opener. ... OK?" dialogue box. It didn't matter how long you stared at it. Or tried to ALT-TAB around it you knew. You were going to lose all your unsaved work. And you were given no choice but to agree.

[@RobMoerland]

I always like the old TaskManager. A highly efficient layout showing all the information I needed as a nerd.

[@UncleKennysPlace]

In the olden days of _shareware,_ I had a product that replaced task manager with a true window manager (you could set the order, force on to float, etc.) It took off when featured by a British mag called _What PC?_ Most of my sales were from Germany and England. It was widely stolen, as well! An old version on modern windows shows all kinds of hidden stuff.

[@glasser2819]

discovering TaskMgr gave us the freedom to quickly terminate runaway processes. As a former "VI" user... working with the CLI gave us the sense of previlege to have a GUI with "CP/M" OS then later stackable Windows (Win3.0). 👏

[@ThePrimeMinisterOfTheBlock]

Loving your work Dave. It's so surreal speaking to one of the people that wrote the operating system/s I've been using for so many decades

[@JonathanPeel]

I will be honest, I always liked the task manager screen. I could very easily see what details I needed. Sometimes, engineers build better screens than designers, because they are actually functional.

[@DQSoft]

If you haven't, you should check Joel Spolsky's User Interface Design for Programmers. Some real good examples of real bad user interface (Windows Help asking you how to build its index is a personal favorite).

[@x057wind]

Hehe 8:35 That looks like Runescape to me! Back when you used to be able to make bonfires you could add logs to the fire to gain XP I love your videos and happily watch them whenever I can! Thank you so much for all the amazing content!!

[@Andrew_Fernie]

I always had to tear myself away from watching the old scandisk. Its was strangely mesmerising.

[@nickbooker5579]

That, and I tended to watch the defrag UI (both the Win9x one's detail view and the WMC based one in win2000 upwards).

[@jdgdesign]

As someone who started out learning how to use computers with MS-DOS on hand-me-down hardware I encountered your Retry-only error a number of times, which was then followed by check disk which usually showed numerous errors and in most cases ended with a dead hard disk. The disk write error was annoying at first because it seemed pointless, but after the second drive failure it started to make sense. After all, no one wants a programmer or "the computer" arbitrarily deciding when fatal data errors can be ignored. So cool to hear the logic and backstory on code choices like the disk write error, task manager and even the disk format interface.

[@eDoc2020]

One thing I absolutely _hate_ about the new Windows Settings app is that only one screen can be shown at a time. When opening some settings there's no reason it should kick you off of a completely different page.

[@zzzzUS]

2:41 And yet here we are with Windows 11, when some basic options just get removed for the sake of simplicity(?)

[@everyhandletaken]

It’s like you are under the impression they care about the user? 🤔 interesting concept.. You can leave your data & wallet by the taskbar on your way out, it will be collected by an MS bot shortly. Feel free to take 1 Mentos from the bowl, though 🙃

[@PaulPassarelli]

Hey Dave This wasn't exactly what I expected, but I gotta say I really enjoy your stories. So, I remember this dialog box from the way-back-when and I was wondering if you know the person who coded the dialog box with the following text? "Bald pink things. The power to rip your head off." [ok] with an image of a large pink troll with clawed hands. It was definitely one of the beta projects, I can't say for certain if it was "Windows for Workgroups", Chicago, or NT

[@JoveMalcolm]

This explains where the only useful parts of windows UI come from... one of the coders, not an artist.

[@nickwallette6201]

Truth. The UI guys spend way too much time looking at a Photoshopped mock-up of an empty window. The minute you need to do anything productive, the minimalistic facade crumbles, and we're left with a simple question: Does it work, or not?

[@user2C47]

Not sure about validity, but I read somewhere that the Win8+ UI was made by executives in PowerPoint.

[@c5gcd]

My all-time favourite bad dialogue goes back over 40 years and can still be seen today:- "Bad or missing keyboard. Press F1 to continue."

[@MWGrossmann]

1:10: Thank you! All these years and I'd never known, let alone actually disappearing the frame. I finally have my Win7 TaskMan back to useful. I knew it had to be a rogue design -- it's the only utility without an Interface for Grandma. Same for that clean and simple format dialog.

[@Ikkepop]

How refreshing to see a lithuanian name in this context every once in a while :D

[@BennyTygohome]

In the mid 90s I was developing Yard Management Software (YMS) for tractor trailer yards. It used handheld scanners with keypad and small liquid crystal display and theyd use it to scan trailer tags in the yard etc. I was limited to how much i could display in the menus so i tried using my own abbreviations when i could... To "continue" i simply used "Cont." in the bottom corner to show there were more menu options continued on the next page. My friend, the project director, said "you know all the drivers are going to laugh because of the CONT." I'm freaked out but it was already too late and close to releasing. I think they loved it.

[@EricParker]

Really interesting perspective on UI design of Windows in the 90s. Curious, have you seen ReactOS, if so what do you think about it?

[@ehsnils]

I like the XP Task manager a lot more than the Windows 10 one that's just not doing it for me.

[@RowiDankelsaft]

8:47 Not as populated, but this reminds me *a lot* the dialog to pick IRQ, DMA and address for sound cards in Windows 3.1x when you were installing Sound Blaster cards. I have no idea if it was the same in NT 3.5x though.

[@saltyowl3229]

The honesty when you asked for the subscribe just saying you liked the dopamine from it is what actually got me to check and hit it. Asking for subs cause it somehow vaguely affects the algorithm and hasn’t affected notifications for years is kinda just meh, but if it can make someone happy just through seeing it, that’s pretty well worth the few seconds to me

[@Howtheheckarehandleswit]

In my opinion, UI design should not require any kind of qualification to rate beyond the qualifications you’d need to use the end product at all; the entire point of UI is to present the options to the user in a way that they can understand without being distracting, if it doesn’t do that for an end user, any end user, it has failed.

[@JanStrojil]

The worst one (number one) seems ridiculous but it is what car manufactures are doing when they replace a rotary dial by cheaper touch controls.

[@shortguy1952]

Dave, I hate to admit this, but after looking at several of your videos, I am older than even 8 inch floppies, thought IBM-XT was the crown of creation and understand a lot of the things you speak fondly of. Yes, I'm 71 years old. You'll get there.

[@NorthshireGaming]

Actually, just catching the first example that popped up in the browser, my first thought was, "Yeah, that's pretty bad, but I'll do one better: A drop down menu with every number combination in numerical order from 0000000000-9999999999."

[@RandomizerYevhen]

The 'space invaders' can work if each column has only one number (1 in first, 2 in second etc.). Just need enough lines for your digits amount.

[@user-mc7ez6lm4x]

Thank you for the smartDrive! It came in so handy when you need it to install Windows NT from hard drive onto ard drive itself. And having only one computer back in the day I could not resist the temptation to try out all the new versions of windows, of course pirated, so smartDrive was like a magical incantation for those windows setup programs.

[@vinzzbe]

Worst sentences that M'sft uses for check-boxes / boolean expressions: - Visual Studio EF Scaffold: "Pluralize or singularize generated object names." (which is it when checked? True = pluralize) - SSRS: "Show or hide based on expression" (which is it when expression evaluates true? True = hide)

[@ailivac]

15:30 "0" taking longer to dial influenced how some of the first area codes were picked. Large cities that people would be expected to call long distance often got codes like DC's 202 or Chicago's 312, while Hawaii ended up with the slower to dial 808. (The second digit had to be 0 or 1 at first for compatibility with how local switching office equipment worked)

[@EdwinvandenAkker]

12:28 _You know how to stop Canadian bacon from curling?_ *Take away the broom!*

[@richardrisner921]

I agree with not wanting to dumb down Windows and remove functionality. That's why I'm not getting Windows 11.

[@TzOk]

15:31 Did you know, that there was more than one standard of the rotary dial? In UK, numbers on the dial were 1, 2, 3, 4, 5, 6, 7, 8, 9, 0, while in Sweden they were 0, 1, 2, 3, 4, 5, 6, 7, 8, 9. In both cases, numbers are given in order from the closest to the limiter (so, the quickest to dial).

[@kissfan003]

Great Channel Dave! I appreciate your work!

[@therackstar]

Thanks Dave. Your channel has quickly become my favorite.

[@JVHShack]

@Dave Your GMC is beautiful. My dad bought a 1971 C10 in the mid-80s and he still has it now.

[@SJ-co6nk]

The new stuff looks really pretty, but we're 10 years in and almost able to set an IP address properly. We still end up going back to windows 95/nt4 era dialog boxes just to do basic configuration. Makes you appreciate how much good work went into the old OSes.

[@kimdahl4152]

I am sorry if this has already been posted. I just remember a classic Win95 startup error message: Keyboard error or keyboard not detected. Press F1 to continue.

[@pr0xZen]

Aye, fair enough. Subbed. Happy New Year, and enjoy your dopamine burst. Well earned.

[@sharkinahat]

Unnamed Editor that has save-on-exit feature. It shows a message "You're about to exit without saving." with the options "OK" and "Cancel".

[@caffeineau]

Back in my early days programming with vc6 and mfc, I ran into a limit of 128 controls on a window. That's when I stepped back and thought 'maybe there's a better way' 😏