To digital natives, Microsoft's IT stack makes Google's look like a model of sanity
- Reference: 1759135393
- News link: https://www.theregister.co.uk/2025/09/29/dont_even_consider_microsoft/
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We originally interpreted the title of Lionel Barrow's blog post, " [1]Don't even consider starting with Microsoft ," to mean starting a job with Microsoft, but no. In fact, the subtitle is more descriptive: "In which a G-Suite user navigates the upside-down world of Exchange, 365, and SharePoint." It's a fascinating glimpse into how horrifyingly complex, even irrational, the Microsoft 365 software stack looks to someone who is used to the Gmail way of handling such business communications: groupware, as it was called in the ancient times. Email, user accounts, file sharing, and so on.
The impression is not good. His criticisms are many, varied, and categorized: Outlook and Calendars, SharePoint and OneDrive, "Everything is an everything application," then Groups, and finally a conclusion. Significantly, that links to the excellent " [2]PHP: a fractal of bad design " article from 2012, which we highly recommend to anyone not familiar with it.
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His gripes range from simple UI issues:
There is no way to make your default view in Outlook put unread messages at the top.
To obscuring rather than highlighting important information:
By default if you decline a meeting invite, that meeting completely disappears from your calendar.
Via entire concepts that should be long obsolete:
Why is "Syncing" Outlook a thing? It's 2025. My email should be syncing automatically.
Some of the basic assumptions are strange to someone who didn't grow up with this stuff:
There's a weird conceptual gap between Outlook's calendar system and Google Calendar: in Outlook, meetings seem to only be updated via email.
He points out multiple ramifications of this. You can invite someone to a meeting that isn't yours by forwarding an email, but if the time of a repeating event changes, they won't be informed. Meeting notifications, including cancellations, are emails and get threaded in with comments, making changes very easy to miss.
He concludes, and we can't fault him:
I was surprised at how badly thought out this all seems.
Moving on to SharePoint and OneDrive, he explains something that we're sure makes sense to Microsofties:
These two are the strangest Frankenstein in Microsoft's menagerie. They're actually the same product presented as two different apps.
This too has unexpected consequences, such as the source of comments on shared documents. New comments come from "SharePoint Online," but replies come from a user account instead – even if they're the same person. He documents his discovery:
SharePoint and OneDrive are ostensibly separate applications, but they aren't. Every file "on" OneDrive is actually on SharePoint; OneDrive is just an editing GUI and search/access layer on top of SharePoint. Except, SharePoint also has its own search and access layer.
He then goes on to note various inconsistencies between different views of the same shared data. Depending on where you are, in which "app" – which are all just web pages now, remember – the search box might search your emails, or your OneDrive, or Contacts, or Tasks, or Teams meetings. They all look similar, they all have search, but what you're searching depends on how you got there.
When he moves on to how Microsoft 365 handles groups, there are no more explanations of how and why things are this way, because it's unfathomable. There are groups in Outlook, and also Distribution Lists, which are different. There are more groups in his MS Exchange Profile, which are different from the groups in his MS Exchange Account. Both are different and separate from Microsoft Entra groups. Depending where he looked, he found himself to be in two, or 11, or 12, or maybe more.
Making sense of this landscape led me to my favorite Microsoft IT moment so far: the site where you administer Exchange Distribution Lists gently suggests that you "consider using a new Microsoft 365 Group."
[…]
So, whatever, this all makes the decision to stop using Distribution Lists and start using M365 Groups all the easier, right? Wrong. Because You Cannot Nest Microsoft 365 Groups. That's right, the core use case of using groups to hierarchically organize your team – the main thing I want to do – is not supported by Microsoft's suggested product. Um. What?
It's a fun read. Decades ago, this vulture was a certified MS Exchange Server admin, and ran umpteen Windows NT Server domains too. There was a point where some of this stuff sort of made sense, but the beginning of our personal transition to Linux was the introduction of Active Directory with Windows Server 2000. AD's complexities easily outdid those of Novell Directory Services, which [4]destroyed Netware 4 in the market – and ultimately Novell. We did keep up with it – [5]The Register Guide to Windows Server 2012 was evidence of that, but it's gone now, [6]except for an extract .
[7]Mr Barrow is clearly a smart chap. In the post, he says: "Every job I'd ever had since finishing college 15 years ago had used Google for IT." That time at college would appear to [8]mean a Masters in Computer Science . Leaving college a decade ago, presumably in his early to mid-twenties, implies he's in his thirties now: a [9]millennial .
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It's not so strange that in [12]several companies over a decade, they all used Gmail. It's easy, it does the job, it works on all major OSes, and has good clients for smartphones. There are good reasons it has thrived, and it was [13]already around a decade old when Barrow graduated.
There are important points to take away from this, we feel, for Microsoft, and for other vendors too. Having worked on several "Agile" projects in the past, this vulture regards the whole concept as somewhere between superstition, faith healing, and outright mythology, and mostly, rather annoying and inapplicable to almost everything to which it's applied. However, there are valuable nuggets buried under the flimflam of standups and sprints and scrums and kanban boards. The concept of [14]Just Barely Good Enough (JBGE) is for us one of the most important.
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Over decades, multiple companies have gone up against the duo of Microsoft Outlook and Exchange Server. Most employed the same tactics: go head-to-head with something as functionally complete as possible, but with some other advantage, such as being cheaper, or more scalable, or based on FOSS.
HP OpenMail was at one point a highly compatible rival, but the company ended up [16]flogging it off to Samsung . Samsung Contact was [17]discontinued in 2007. Another fork became Scalix, later [18]acquired by Xandros , the [19]inheritors of Corel LinuxOS .
[20]Bcachefs goes DKMS after Torvalds' kernel banishment
[21]Zorin OS 18 beta makes Linux look like anything but Linux
[22]MX Linux 25 reaches beta testing – complete with systemd
[23]Linux's love-to-hate projects drop fresh versions: systemd 258 and GNOME 49
In 2005, we reported that the FOSS Open-Xchange boasted [24]90-95 percent of the functionality of Microsoft Exchange and SharePoint . It's [25]still around , and claims over 220 million users. A survivor, as is
Lotus HCL Notes, [26]which is still around , but we suspect wins very few new customers. We've seen [27]multiple different [28]estimates that several tens of thousands of large companies still run Notes, which implies at least a few million active users. Even the former Novell, now [29]OpenText Groupwise , is still around. It [30]may have tens of thousands of users.
Put them all together, and… oh, about [31]one-tenth of Gmail , then.
It has won. The entry level is free, it does the job, the web client is still good today – it even does [32]plain-text email and interleaved quoting [33]like a pro . It works with legacy clients too. While millions of middle-aged managers kept working with the same old familiar devil they knew, the red/yellow/blue/green weed was spreading, and now, a new generation of people grew up with this simpler tool and it does all they need.
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Gmail isn't perfect, it doesn't do all the things that all those other groupware packages do – but even when it was introduced, over 20 years ago, it was Just Barely Good Enough to compete, and it's stayed relatively small and simple since. It does the essentials.
It is worth remembering that some of the core Google Workspace apps were bought in. In 2006, Mountain View [35]acquired Upstartle for Writely , which became Google Docs, and months later, [36]2Web Technologies , whose XL2Web became Google Sheets. The next year, [37]it bought Zenter , which [38]along with Topic became Google Slides. The point being that these are later, bolt-on extras: they weren't originally part of the core Gmail offering, and they're easily replaced by full-fat local apps.
This vulture installed a lot of Outlook in the late 1990s, and for the bigger clients hooked it up to Exchange Servers – and fixed them when they filled up and fell over. What Outlook could do for a keen executive was unbeatable. Outlook meant Exchange, and Exchange required Windows Server, and that meant adopting Active Directory. They were sine qua non of any serious growing organization.
A quarter of a century later, the previous generation's essential power-user tools, from Active Directory and Group Policies up to this week's iteration of Office 362.5, are the next generation's baffling arcana. Microsoft successfully migrated its legacy stack of Windows binaries to JavaScript in the browser, which is impressive, but in doing so, it kept all the complexity. To product management, we suspect that those power features are the selling points. Ripping them out is inconceivable.
Which is how we arrived at Windows 11, with mandatory cloud accounts even at home, built-in nag screens telling paying users that they need more OneDrive space, the [39]unloved Teams pinned to the immovable taskbar, bundled [40]LLM-bot slop generation , and adverts for additional payware [41]in what's left of the Start menu . Once Windows uniquely exposed its users to the risk of spyware, but Microsoft has fixed that [42]by pre-installing it for your convenience. Oh, and some [43]added incentives to buy in for people on the older version.
It smacks of desperation to us.
There are options. Microsoft was once a renegade startup. It could assemble a team bold enough to take the chainsaws to Windows, Office, and Outlook, and brutally prune them down to something tiny and minimal and Just Barely Good Enough. Back in the Windows 7 era, it [44]demonstrated MinWin , which cut the core of Windows 7 down to something as small as Windows 95: about 25 MB. That's the spirit.
Meanwhile, as we have argued before, the [45]FOSS world really needs a minimal ChromeOS rival . We admire the sentiments behind the [46]EU OS proposal , but not the choice of tech to implement it. For us, the [47]KDE Linux project is a better design, but KDE itself is top-heavy these days. We'd like to see a "KDE Litem" pruned back to the core desktop functionality of Windows 95 and NT 4.
We really enjoyed Mr Barrow's tour of madness. It's nearly three decades since this vulture fought this stuff daily, but we have never missed it, and it brought a wry smile to our face to see how strange it all seems to a 21st century adult. ®
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[1] https://lionelbarrow.substack.com/p/dont-even-consider-starting-with
[2] https://eev.ee/blog/2012/04/09/php-a-fractal-of-bad-design/
[3] https://pubads.g.doubleclick.net/gampad/jump?co=1&iu=/6978/reg_offprem/saas&sz=300x50%7C300x100%7C300x250%7C300x251%7C300x252%7C300x600%7C300x601&tile=2&c=2aNpYs8Ur4ZMjkbdZb9JjsgAAAUM&t=ct%3Dns%26unitnum%3D2%26raptor%3Dcondor%26pos%3Dtop%26test%3D0
[4] https://www.theregister.com/2013/07/16/netware_4_anniversary/
[5] https://www.theregister.com/2013/02/11/guide_to_windows_server_2012_ebook/
[6] https://www.theregister.com/2013/04/10/hyper_v_book_extract/
[7] https://lionelbarrow.com/
[8] https://www.computerscience.uchicago.edu/people/lionel-barrow/
[9] https://www.bamboohr.com/resources/hr-glossary/millennials
[10] https://pubads.g.doubleclick.net/gampad/jump?co=1&iu=/6978/reg_offprem/saas&sz=300x50%7C300x100%7C300x250%7C300x251%7C300x252%7C300x600%7C300x601&tile=4&c=44aNpYs8Ur4ZMjkbdZb9JjsgAAAUM&t=ct%3Dns%26unitnum%3D4%26raptor%3Dfalcon%26pos%3Dmid%26test%3D0
[11] https://pubads.g.doubleclick.net/gampad/jump?co=1&iu=/6978/reg_offprem/saas&sz=300x50%7C300x100%7C300x250%7C300x251%7C300x252%7C300x600%7C300x601&tile=3&c=33aNpYs8Ur4ZMjkbdZb9JjsgAAAUM&t=ct%3Dns%26unitnum%3D3%26raptor%3Deagle%26pos%3Dmid%26test%3D0
[12] https://www.linkedin.com/in/lionelbarrow/details/experience/
[13] https://www.theregister.com/2014/04/01/gmail_tenth_anniversary/
[14] https://agilemodeling.com/essays/barelygoodenough.htm
[15] https://pubads.g.doubleclick.net/gampad/jump?co=1&iu=/6978/reg_offprem/saas&sz=300x50%7C300x100%7C300x250%7C300x251%7C300x252%7C300x600%7C300x601&tile=4&c=44aNpYs8Ur4ZMjkbdZb9JjsgAAAUM&t=ct%3Dns%26unitnum%3D4%26raptor%3Dfalcon%26pos%3Dmid%26test%3D0
[16] https://www.theregister.com/2002/04/12/openmail_lives_again/
[17] https://web.archive.org/web/20080206080236/http://www.samsungcontact.com/
[18] https://www.theregister.com/2007/08/15/xandros_microsoft_license/
[19] https://www.theregister.com/2001/08/30/corel_licenses_off_linux_distro/
[20] https://www.theregister.com/2025/09/25/bcachefs_dkms_modules/
[21] https://www.theregister.com/2025/09/24/zorin_os_18_beta/
[22] https://www.theregister.com/2025/09/23/mx_linux_25_reaches_beta/
[23] https://www.theregister.com/2025/09/23/systemd_258_gnome_49/
[24] https://www.theregister.com/2005/04/05/netlin_open_x-change/
[25] https://www.open-xchange.com/
[26] https://www.theregister.com/2025/09/23/hcl_notes_domino_support/
[27] https://trinus.com/living-with-legacy-applications-like-notes/
[28] https://enlyft.com/tech/products/ibm-lotus-notes
[29] https://www.opentext.com/products/groupwise
[30] https://theirstack.com/en/technology/micro-focus-groupwise
[31] https://www.demandsage.com/gmail-statistics/
[32] https://useplaintext.email/
[33] https://www.theregister.com/2023/08/23/email_like_a_pro/
[34] https://pubads.g.doubleclick.net/gampad/jump?co=1&iu=/6978/reg_offprem/saas&sz=300x50%7C300x100%7C300x250%7C300x251%7C300x252%7C300x600%7C300x601&tile=3&c=33aNpYs8Ur4ZMjkbdZb9JjsgAAAUM&t=ct%3Dns%26unitnum%3D3%26raptor%3Deagle%26pos%3Dmid%26test%3D0
[35] https://www.theregister.com/2006/03/10/google_writely/
[36] https://mergr.com/transaction/google-acquires-2web-technologies
[37] https://www.theregister.com/2007/06/20/google_zenter_carbon_icp/
[38] https://www.theregister.com/2007/09/18/google_presentations_live/
[39] https://www.theregister.com/2021/07/21/windows_11_teams/
[40] https://www.theregister.com/2025/09/19/microsoft_copilot_marketing_blitz/
[41] https://www.theregister.com/2024/04/24/adverts_windows_11/
[42] https://www.theregister.com/2025/08/01/microsoft_recall_captures_credit_card_info/
[43] https://www.theregister.com/2025/06/25/microsoft_free_esu_tier/
[44] https://www.theregister.com/2009/11/18/windows_7_heart/
[45] https://www.theregister.com/2025/07/21/foss_chromeos_please/
[46] https://www.theregister.com/2025/03/25/eu_os_free_govt_desktop/
[47] https://www.theregister.com/2025/08/04/kde_linux_prealpha/
[48] https://whitepapers.theregister.com/
The reliance on GAM to do pretty much anything that you wouldn't ever want to do in bulk with no rollback, is dia-bloody-bolical.
FTFY.
OneDrive is Sharepoint?
Oh dear god, why? Does this mean any Enra ID Sharepoint access has access to all of our inadvertent OneDrive files? I wonder if we can turn off OneDrive and repatriate the files?
Re: OneDrive is Sharepoint?
Default settings for a OneDrive Sharepoint site only allow the site owner to access the content.
Re: OneDrive is Sharepoint?
But we've never set up a OneDrive Sharepoint site...
The site owner shouldn't have any access, except by jumping through dual-approval, to any of the OneDrive/Sharepoint files.
Re: OneDrive is Sharepoint?
They're not exactly the same thing but, yes, one is bolted onto the other and I think Sharepoint is the main reason why OneDrive is so incredibly slow when compared with, say, rsync, Google Drive or Dropbox.
Why would I want to know about a meeting I've declined? If I declined it I don't want to go to it, or can't go to it. Why should it clutter the calendar?
And why has this person made me defend Outlook?!? FFS it's only Monday and I'm already annoyed.
But Outlook does show declined meetings. It gained this feature a year or two ago.
Marketing to the rescue
Don't worry, MS marketing will be along shortly to rename everything.
Re: Marketing to the rescue
Yes, they will rename everything to the same name so nobody knows exactly what anyone else is talking about.
See Outlook (Hotmail), Outlook (OWA), Outlook (Desktop), and Outlook (Microsoft 365).
Groups
Groups in the Microsoft world are a mess.
Exchange mastered groups, Entra mastered static groups, Entra mastered dynamic groups, AD mastered groups, Office 365 groups. (Have I missed any?)
Each flavour has slightly different features & capabilities and you can't always mix them. Nor can you convert between them.
Groups usually support nesting - but applications need to be specially written to support nested groups: It's hit and miss as to whether nesting will work. So you end up writing scripts to de-nest groups. (In an ideal work you'd used dynamic groups - except updates can take 24 hours and not all applications support dynamic groups)
Re: Groups
Try finding permissions set on subfolders…
Re: Groups
>>Groups in the Microsoft world are a mess.
They were pretty straight forward back in the day. Sadly they have suffered the ravages of time and software "improvements"
>>Exchange mastered groups, Entra mastered static groups, Entra mastered dynamic groups, AD mastered groups, Office 365 groups.
>>(Have I missed any?)
Yeh. InTune groups - they work worse than any of the others....
The siloing of products inside Microsoft has lead to the dog's dinner that we suffer today. Every silo has "NIH syndrome" with respect to things developed in other silos and then someone decides it should all be OneMicrosoft and here we are with sticky tape barely covering the cracks.
>>In an ideal work you'd used dynamic groups
Yeh - I would if I could define the rules based on any Entra/AD user attribute rather than just the ones Microsoft deem sensible (State or Province, Company, Department, Custom Attribute[1-15]) and also have multiple rules with definable logic for each group (like you can for (on prem)AD GPO targetting; yeh that isn't great either but that's a UI thing rather than a functionality thing). As it is I have to mangle the usage of state, company & department to not mean what they imply to get anything that vaguely fits my use case.
His mistake is in thinking it was designed...
None of this was designed at a larger scale. It's a mess because the industry has been messy.
Taking SharePoint as an example, it was built to provide a web-based Groupware system.
Microsoft's first attempt at Groupware was Exchange Public Folders, which were pretty bloody awful yet somehow still exists today. Meanwhile the web was happening, everyone wanted an Intranet, and Microsoft had no product for this. Well - they had IIS as a server, they had Office putting out HTML, but unless you wanted to upload your files via FTP or maybe tinker with WebDAV (remember that?), you were out of luck in Microsoft's portfolio.
Meanwhile, Lotus Notes has gained a webserver and can publish your applications to your intranet without much work at all. Yes, they're ugly as hell, but this is 1998 and most websites are ugly as hell - what terrifies Microsoft is that you can convert Notes applications to web applications with a few simple changes to your servers.
So SharePoint was born. It was a supermarket sweep trolley dash of technologies, taken from various Microsoft teams - Office, Development Tools, Server. It was such a rush job that a version 2 came out fairly quickly afterwards that broke compatibility with the first version.
SharePoint was never designed to scale up, or to be easy to integrate. It had a reputation as being a big, heavy, awkward product that nobody loved, but that fitted with company's IT strategy so was used anyway.
The fact that we're still using it is mildly shocking. SharePoint should have died years ago. It's one of the least popular offerings from Microsoft - for all their audiences. Developers, administrators, users - they tolerate SharePoint, knowing that better solutions are available but that this is what the IT strategy says we have to use.
The real surprise is that, having bought Groove, they then decided to integrate it with SharePoint and later use the Groove sync client to create OneDrive. Again, that wasn't part of any long term plan. It just happened. Microsoft needed personal storage, and they rummaged around in their product bag to see what they could cobble together quickly.
Give it twenty years, people will be saying the same thing about Google's platform. Their big advantage currently is that they offer a lot less, so there's less to integrate. That can't last...
Re: His mistake is in thinking it was designed...
The fact that we're still using it is mildly shocking. SharePoint should have died years ago.
I wouldn't be surprised if they decided not to kill it but to carry on and push corporations onto it at about the same time they were told to open up SMB. No money goes to Microsoft if everyone can set up their own Samba servers.
But have they actually tried to administer G-Suite? What an absolute crock. UI navigation is something otherwordly, and the reliance on GAM to do pretty much anything in bulk is dia-bloody-bolical.