I'm actually afraid to comment in case I win
Apply here to win a Microsoft Ugly Sweater. It's uglier than ever
It's that time of year again when Microsoft dispatches its latest Ugly Sweater to The Register, and we spoil a lucky reader that makes us smile by sending you the garment in time for Christmas. Compared to previous incarnations, 2025's jerseys are a slightly more sober affair. There are three. The Artifact Sweater features a …
COMMENTS
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Tuesday 2nd December 2025 14:07 GMT stewrogers
Peak Microsoft is the short-lived Windows phone. They already had a decent product in Windows mobile, but then an arrogant lack of innovation caused it to fall behind when, first Blackberry, then Apple and Google raced right past them, so they bought Nokia and produced the actually fantastic Windows Phone, brilliant devices - then even had a funeral for iphone. Got next to Zero traction because they were so late to the game and ultimately wrote off the whole division....
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Tuesday 2nd December 2025 15:56 GMT GlenP
I liked Windows Mobile, and for a while it was the best option for business use, then Microsoft lost interest or dropped the ball and even their own apps weren't getting updated.
Work wise we were heavily Blackberry with a few Nokia dumb phones around, mainly due to the benefits of BES reducing data volumes, once that all changed and iPhones became common I was pressured into changing and couldn't really argue!
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Tuesday 2nd December 2025 14:28 GMT ParlezVousFranglais
1996 - Exchange 4 and the associated version of Outlook - IMHO the only reason that Windows is still around as the dominant business desktop. By managing eventually to all but wipe out Notes and Groupwise, that locked most of the business world into MS Office and thereby into Windows. (Exchange 4.0 was a sod for exploding without warning, and often a complete bitch to restore properly, but that's the fun of being in IT...)
Interestingly MS don't seem to understand that by slowly shifting the code behind Outlook from native Windows to web-based, that could eventually break the need for most enterprises to standardise on Windows
The real "year of Linux on the desktop" might not now be too far away... (much like Nuclear Fusion ツ)
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Tuesday 2nd December 2025 19:16 GMT Roland6
> 1996 - Exchange 4 and the associated version of Outlook
After all the multi year hype about Microsoft’s Enterprise Messaging System, the actual release was a bit of a let down.
Same applied to Windows Embedded, loads of vapourware and the. They released Wince which similarly didn’t match the hype.
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Tuesday 2nd December 2025 15:04 GMT goblinski
I was thinking - swimming with sharks, but - like for most things in life - Malcolm has it fully covered.
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Tuesday 2nd December 2025 15:05 GMT Steve Powell 1
Flushing $7.6bn down the drain buying Nokia and then telling them how to do phones using a crappy photocopy of Apples homework. Writing the whole thing off within 2 years.
Mind you the competition is pretty hot. The $26bn they spaffed on the uber-spam/bullshit engine that is LinkedIn has to be the biggest lump of money ever spent on making yourself even less popular than you already were.
This is a pattern they seem to be repeating with Blizzard so we may not have seen peak MS yet, especially if the AI bubble bursts, maybe OpenAI will turn out to be peak MS.
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Tuesday 2nd December 2025 15:11 GMT Dwarf
I'd prefer a coat
I'd prefer a coat to a sweater, that way, I have something to protect me from the clouds.
Now, If only we could find something to protect against the AI.
Looking at the sweater, it shows how many things, that they thought were important are now completely irrelevant to us.
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Tuesday 2nd December 2025 15:17 GMT Roland6
“ When do you reckon we hit peak Microsoft, and why?”
‘Do’ seems to imply future not past.
Which suggests when will MS surpass themselves: I suspect it will be with the update to Windows 12, which will be Copilot (aka AI0 assisted. Were we can expect “Clippy” wanting to be helpful, will in “preparing your system for upgrade” delete the hard disk in readiness before downloading the new install file…
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Tuesday 2nd December 2025 15:26 GMT My other car WAS an IAV Stryker
I want this for "ugly Christmas sweater" contests (icon)
Peak MS to me was when we had to start caring about Microsoft at all -- mid-to-late 1980s DOS days: To go with our PC clone, Dad got a real IBM PC DOS set from work (manuals in custom-sized binders with 5-1/4 inch "'diskette" pockets, all in a cardboard case, all beige/pale pink) -- I believe it was 2.1. But my older brother quickly found out he couldn't play the latest sneakernet games without an upgrade, and it had to be "genuine" MS-DOS (we mostly used 3.3, maybe also tried 4.something).
That was peak: Microsoft or bust. Computers at school that weren't Apple had DOS, mostly to use WordPerfect, even into high school (mid-90s). I could even fit my own DOS files on a 3-1/2 inch disk and reboot into my own ANSI.sys boot screen / menu and play some games [1].
Windows (3.1) was just a (slow) add-on until it started taking over everything, especially with Win95 [2]. It's all been downhill since.
Bootnotes:
1) Mostly runtimes from QBasic like Nibbles and Gorilla, back when the chips were slow enough.
2) And when Win95 hit, the whole school switched at once and forced us into MS Office from there on (save for Pagemaker for the student newspaper plus the proprietary yearbook layout program).
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Tuesday 2nd December 2025 15:26 GMT wolfetone
Micro$oft peaked when they released Clippy.
And I would quite like the jumper, and I promise to wear it the day my wife goes in to labour for our second child which is due 23rd December. I can provide photographic proof. Given how it's been during the scans, there is every chance it'll just turn up at the most in opportune time - when I'm sat down for Christmas Dinner lunch wearing that jumper.
Make my kid's christmas great! For the first time anyway.
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Tuesday 2nd December 2025 16:37 GMT MyffyW
2001: Peak MS = Slough of Balmer?
I think Balmer referring to Linux as "Cancer" has to be the point when MS realised how dangerous Linux was to their server OS business.
I mean, seriously Steve, at least SNAP! got a useful rhyme out of using the "C" word.
He might have lacked Charisma, Uniqueness, Nerve and Talent. But Balmer sure knew how to look like one.
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Tuesday 2nd December 2025 15:56 GMT Wally Dug
Subjective
Of course, the "peak" for Microsoft will always be subjective. Some people may say it's Windows 7, some Windows XP SP3 and others Windows 98 SE SP2.
Then there's Office. For me, I feel that Word 6 and Excel 4 offered everything that I have ever needed in a word processor and spreadsheet application, and there is no need for all the added-on bloat in subsequent versions.
So, how about this? A stripped down version of each with the basic functions only for normal users, sold at a reduced price. Let's call them Word and Excel. Then, additional "extra large" versions with all the added bells and whistles that they currently have for the premium users, with an "extra large" price tag, too.
Let's call them Word XL and Excel XL.
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Tuesday 2nd December 2025 16:04 GMT GlenP
Re: Subjective
They had a stripped down all-in-one package, Microsoft Works (and if that isn't an oxymoron I don't know what is! :) ). I first encountered it in probably the early 90s when it came free with a new PC and it wasn't too bad for the basics. Having looked I'm slightly surprised it lasted until 2009.
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Tuesday 2nd December 2025 15:59 GMT TheNix
Stolen
Steve Ballmer telling the world that "The most common format of music on an iPod is 'stolen'" (https://www.theregister.com/2004/10/04/ballmer_ipod_thieves/).
Pure Microsoft: insult your (potential) customers ("You guys are thieves!"), and demonstrate a willful ignorance of the underlying technology ('stolen' is a format?!).
The nadir of Ballmerism in a highly competitive field.
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Tuesday 2nd December 2025 16:02 GMT AlnotAI
It has to be Microsoft's 25th anniversary event in September 2000 with Steve Balmer doing his Monkey Boy Dance, running on stage yelling "I LOVE THIS COMPANY!!!" (not to be confused with his sweaty "DEVELOPERS DEVELOPERS DEVELOPERS"! dance a few months before in July, which was almost peak but not quite)
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Tuesday 2nd December 2025 16:02 GMT ChefBytes
Ah, the good old Christmas jumper. I'd be more than interested in one of these hideously unfashionable garments if only to be worn to our Christmas Party. Like the good old Windows ME I expect to be crashing within the first couple of hours, so to have something to wear that will advertise this would be superb!
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Tuesday 2nd December 2025 16:28 GMT MyffyW
MS-DOS - Version 6.x
Controversial, I am sure, but hear me out:
This was the pinnacle of MS-DOS.
Yes, future versions came out tied to the 9x products, but with built in utilities covering automation of memory management (MemMaker), disk compression (DblSpace, sorry DrvSpace), PC-to-PC file transfer (Interlnk) and an anti-virus engine (it was a nice idea), this felt like a fully evolved product. Albeit a technology cul-de-sac for 386 and above PCs.
Run Windows for Workgroups 3.11 on top of that and it was about as good as you could get in 1993.
Windows NT was definitely a better operating system. But everything that came after MS-DOS 6.x took away the personal aspect of personal computer and put the long arm of corporate policy on top of your desktop.
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Tuesday 2nd December 2025 17:09 GMT GBE
Microsoft C compiler 4.0 for DOS and wired optical mouse.
IMO, Microsoft peaked with version 4.0 of the their DOS C compiler/debugger back in 1986. That was a fine product, with good documentation. The OS it ran on was crap.
The first couple generations of wired optical mice (with wheels) from the mid 90's were also fine products.
Pretty much everything else from MS has been varying levels of awful with an overall downward trend over the decades.
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Tuesday 2nd December 2025 17:22 GMT AlgernonFlowers4
When Disaster Struck and Clippy Answered!
It’s wild to think about, but Microsoft hit its peak with a talking paperclip.
The kids are trapped in a cave, panic everywhere — and suddenly Clippy appears:
“It looks like you’re trying to save your offspring.
Would you like me to create a step-by-step rescue plan?”
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Tuesday 2nd December 2025 17:34 GMT CountCadaver
MSN messenger is where I'll go - got me in contact and kept me in contact with a lot of people, when it died my connection to a lot of others went also.
Software- Word 6.0/97
Operating system - Windows 2000 professional, absolutely rock solid. 7 had more shiny bits but it never quite felt quite as bombproof as 2k professional which barring a hardware failure would probably be found running by aliens surveying the wreck of the planet in a several millennia
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Tuesday 2nd December 2025 17:36 GMT Eambo
I definitely think either around XP SP2 or most likely, towards the end of Windows 7's life was peak Microsoft.
When the OS actually felt snappy, searching for local files actually found local files, and I could find the settings and options I needed, where I needed them.
Windows 10 started off with good promise but it, and 11, just went so far the wrong path they pushed me to get a Mac as my primary machine after 25 years of Windows loyalty (and Admin!)
I pine for those Windows 7 days :)
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Tuesday 2nd December 2025 17:52 GMT Dr. G. Freeman
I don't think we've reached peak Microsoft yet.
Peak would mean a maximum - it still has a little way to go to be totally annoying, unusable, and be a complete waste of space.
Windows 11 and co-pilot are just a camp on the slope, we're not at the summit yet, to put a four boxed flag on it.
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Tuesday 2nd December 2025 18:49 GMT TheGriz
Windows 7 Hands Down
Microsoft clearly reached it's zenith with Windows 7. They still showed they could LEARN from their own mistakes with the unmitigated disaster that was Windows Vista, and went back to the drawing board and released Windows 7, which was the darling of their OS's. Now they have their own heads so far up their own arses, with A.I. <cough>, they can't see where they came from, much less where they are GOING. Suffice to say, the Microsoft of TODAY is a wretched wraith of what it once was. I want the ICON sweater if I win. :D
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Tuesday 2nd December 2025 19:22 GMT jonesp
Peak Microsoft was the Bill Gates cleaning Windows screen saver
You asked for something that would make you smile.
I would say that peak Microsoft was when Bill Gates appeared as an endearing smiling character who pushed his spectacles up his nose and helpfully cleaned the inside of your Windows 3.11 PC screen in a screen saver. That was when Bill Gates was a bit of an office hero who made IBM PCs and compatibles easier to use and more fun with the new Windows, Icons, Mouse and Pointers (WIMP) graphical user interface. Here it is:
https://www.youtube.com/watch?v=dFa37e8d9OQ
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Tuesday 2nd December 2025 20:46 GMT Framerateuk
I've got very fond memories of the late 90's, pre Xbox era games that Microsoft published.
Motocross Madness, Midtown Madness and my favourite, Outwars. It's a seriously cinematic game and doesn't really get the credit it deserves. It has a great atmosphere, the jetpacks were brilliant and the fighting felt frantic.
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Tuesday 2nd December 2025 23:49 GMT Fruit and Nutcase
The Platform...
Let the man himself reveal all...
icon: sweater
As we near the northern winter solstice, need to layer up. If I win the sweater, I'll
proudly[warmly] wear it under a plain hoodie. -
Wednesday 3rd December 2025 10:01 GMT RvS513
July 11, 2011
Peak Microsoft: July 11, 2011.
The first release of PoweBI Desktop.
A free(!) tool to visualize data and connect to almost anything and create data models.
Even the graphs look decent (they explicitly did not want anyone from the Excel team to join).
Subscriptions, cloud and AI have been added now obviously, but the free version is still available and very useful.
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Wednesday 3rd December 2025 10:02 GMT Sambalar
An age of learning
Biggest thing I've learned from Microsoft, the icons you use, and only ever the icons you use will get moved around and hidden in a maze of menu's in their next release..... everything else, carry of as you were!
I recall being around 15 and getting my first 'desktop computer'. Came with Windows 3.1 (I think) and and upgrade to windows 95. Boy oh boy did i cry my eyes out after the upgrade. Could i find anything, no, could i work out how to find things by looking things up on the internet, No. We didn't have internet. All i had was a leaflet about how exciting Windows 95 would be. I'm not sure I'd have used the words 'exciting', for a 15 year old me, it was a traumatic introduction to the world of Microsoft's 'lets mess about with this' roadmap.
I took a career path into the Computing space, my favorite OS, Windows 2000. Why? It had the right balance of a home configurable system but also if you wanted to get under the hood a bit and tweak, you could, without the latter being magically hidden in a dark corner or causing normal home users to be overwhelmed and getting concerned that anything they touch would somehow cause the computer (and the world) to explode.
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Wednesday 3rd December 2025 10:03 GMT JBriggs.DEV
Windows Vista SP2
Vista get's a lot of flack, but when the OS came out it brought along with it features which would transfer over to future operating systems to come. When SP2 came out, a lot of the bugs were ironed out. This definitive version of Windows Vista also fixed the problems introduced with the OS's first ever release. Vista in it's initial release gave us proper user permissions and other UAC features, DirectX 10 and Aero, Desktop Window Manager, and the smallest most important feature being the addition of a search on the start menu. Sure Windows 7 took all of these features and created an operating system which was so good that it held a good market share of users for over a decade, but without the work put into Vista, 7 and other future OS's wouldn't have some of the critical windows features we have today. Unfortunately, with all of these extra features, it created an OS not ready for everyones hardware.
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Wednesday 3rd December 2025 10:05 GMT Will Godfrey
It's a trick question!
It hasn't been reached yet. They are still piling on more crap and will continue to do so until it becomes a singularity, when it will collapse under it's own weight sucking in the entire universe with it.
Unfortunately at that point there will be nobody left to collect the sweater... maybe that's just as well
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Wednesday 3rd December 2025 11:02 GMT Pat Harkin
Peak Microsoft moment?
It's a close call, but I think I'd have to go for 1947 and the invention of the transistor[1].
John Bardeen, Walter H. Brattain, and William Shockley at Bell Labs set us on the path to the future - via Clippy, Windows Vista and Windows ME.
So much potential. Such a waste.
[1] OK, Microsoft didn't yet exist n 1947 but this has Gates' fingerprints all over it. I don't know how he did it - perhaps Copilot can tell us...
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Wednesday 3rd December 2025 14:55 GMT David Hicklin
Peak windows for me was windows 7 , sure they had a few slips down the slippery slope with ME (wtf was wrong wrong with Win 98 SE ?) and Vista but Windows 7 just about pulled them back up enough to be the peak.
After that is has been downhill all the way and the slope is only getting steeper
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Wednesday 3rd December 2025 15:53 GMT sugerbear
Just when you think Windows can't get any worse
They release a Christmas Jumper. I bet if has "AI" on it somewhere.
I can say that the time I enjoyed Windows the most was probably windows 10 before they started to slowly destroy it with "improvements", then kill it off with 11.
Everything after and before.. meh..
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Wednesday 3rd December 2025 16:25 GMT STUNNN
The obvious smile answer is.... We haven't.... lol
The obvious smile answer is.... We haven't.... lol.
The sensible answer is NT was amazing.... 2000 Server! :) Rose tinted glasses says that XP was good (although not when you recall giving it new printer drivers, only for it to reboot and then need new printer drivers, only for it to reboot and need new printer drivers....Grrrr)... Windows 7 - Final Answer... and peak Office 2000 - It just worked! unlike bloody Office 365.
Ok, so give me Windows 7, with an NT GUI and Office 2000 please.
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Thursday 4th December 2025 18:07 GMT Aradalf91
Longhorn was peak Microsoft, in all senses
Longhorn. It was beautiful and promised to bring generation-defining innovation in UI and UX, both for OS and apps. It was a connected, cohesive experience, with some features that were way ahead of its time (like semantic search). Unfortunately, it turned out to be too visionary and Microsoft ended up giving up Vista. I still liked it, but it was absolutely nowhere near Longhorn. This is why it was peak Microsoft: it held a lot of promise and it had all the right things for it to be groundbreaking and successful, and ended up in a disaster. The same happened actually with Windows Phone and with a whole lot of other things, but Longhorn was probably the most striking.
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Friday 5th December 2025 08:04 GMT liquidsmoke66
Win95 on floppy disk option
I remember queuing with my old man to get into pc world on the win95 release day! It was actually an exciting event back then! Long suffering on 3.11, i remember we were feeling smug as we had cd drives. Altho win95 was available on floppy too! The weight of the floppy version made me kinda want that one just cos it felt more value. Lols.