Microsoft's many Outlooks are confusing users – including its own employees
- Reference: 1742908515
- News link: https://www.theregister.co.uk/2025/03/25/too_many_outlooks/
- Source link:
It's a problem common to several Microsoft products. A file needs to be opened, but which app should be used? Should it be Outlook New, or Outlook (New)? With tongue firmly in cheek, Hanselman listed some more options: Outlook (Zero Sugar), Outlook (Caffeine Free), and so on.
Hanselman, Developer Community veep at Microsoft, also included Outlook '95, although to our mind the peak came with the version of Outlook in Office 97. A happier, more trusting time when security was less important.
[1]
While users can create multiple [2]Outlook profiles to store email account details and data locations, Hanselman's [3]post on Bluesky highlights an issue facing many users of Microsoft's software: which incarnation of the application to use.
[4]
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Teams users often find themselves presented with a variety of applications – Microsoft Teams and Microsoft Teams (Personal), for example, can often appear side by side in the system tray.
As for Outlook, users are likely to have multiple versions installed. Microsoft [6]forced the new version onto devices as part of a Windows update and renamed the previous version to Outlook (Classic) so the pair could run side by side. While support for the Classic version of Outlook will persist until at least 2029, Microsoft would like users to move to the new version despite it lacking many of its predecessor's functions.
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[8]According to Microsoft: "The new Outlook for Windows, built upon modern service architecture, is inspired by the Outlook web experience." It also does not support the COM add-ins used by many enterprises to glue corporate workflows together.
[9]Oops, they did it again: Microsoft breaks Outlook with another dubious update
[10]Even Windows 10 cannot escape the new Outlook
[11]New Outlook marches onto Windows 10 for what little time it has left
[12]Outlook is poor for those still on Windows Mail, Calendar, People apps by end of year
Currently, the new Outlook is at the opt-in stage and is off by default. It will then proceed to an opt-out stage, where users must actively switch back to the Classic experience before the Cutover stage, after which reversal is no longer possible. Microsoft says it will give administrators at least 12 months' notice before this is implemented in production rings.
Existing perpetual installations of classic Outlook "will continue to be supported until at least 2029," [13]according to Microsoft.
There is a cautionary tale about [14]what happened when a soft drinks company tried to replace a well-liked product with a "new" version and renamed the previous preferred version as "classic."
The list posted by Hanselman – who is also [15]notable for tips on managing Microsoft's personal information manager – is amusing, but also highlights the perils of having multiple, similarly functioning options to do the same thing, and the potential for confusing users.
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Outlook (Stable and Fast) anyone? ®
Get our [17]Tech Resources
[1] https://pubads.g.doubleclick.net/gampad/jump?co=1&iu=/6978/reg_software/applications&sz=300x50%7C300x100%7C300x250%7C300x251%7C300x252%7C300x600%7C300x601&tile=2&c=2Z-LhLkBn7zjH6q00VzEHUQAAA4I&t=ct%3Dns%26unitnum%3D2%26raptor%3Dcondor%26pos%3Dtop%26test%3D0
[2] https://support.microsoft.com/en-us/office/overview-of-outlook-email-profiles-9073a8ac-c3d6-421d-b5b9-fcedff7642fc
[3] https://bsky.app/profile/scott.hanselman.com/post/3ll5obc6v5c2j
[4] https://pubads.g.doubleclick.net/gampad/jump?co=1&iu=/6978/reg_software/applications&sz=300x50%7C300x100%7C300x250%7C300x251%7C300x252%7C300x600%7C300x601&tile=4&c=44Z-LhLkBn7zjH6q00VzEHUQAAA4I&t=ct%3Dns%26unitnum%3D4%26raptor%3Dfalcon%26pos%3Dmid%26test%3D0
[5] https://pubads.g.doubleclick.net/gampad/jump?co=1&iu=/6978/reg_software/applications&sz=300x50%7C300x100%7C300x250%7C300x251%7C300x252%7C300x600%7C300x601&tile=3&c=33Z-LhLkBn7zjH6q00VzEHUQAAA4I&t=ct%3Dns%26unitnum%3D3%26raptor%3Deagle%26pos%3Dmid%26test%3D0
[6] https://www.theregister.com/2025/01/10/new_outlook_windows_10/
[7] https://pubads.g.doubleclick.net/gampad/jump?co=1&iu=/6978/reg_software/applications&sz=300x50%7C300x100%7C300x250%7C300x251%7C300x252%7C300x600%7C300x601&tile=4&c=44Z-LhLkBn7zjH6q00VzEHUQAAA4I&t=ct%3Dns%26unitnum%3D4%26raptor%3Dfalcon%26pos%3Dmid%26test%3D0
[8] https://learn.microsoft.com/en-us/microsoft-365-apps/outlook/overview-new-outlook
[9] https://www.theregister.com/2025/03/20/outlook_outage_again/
[10] https://www.theregister.com/2025/01/30/outlook_arrives_on_windows_10/
[11] https://www.theregister.com/2025/01/10/new_outlook_windows_10/
[12] https://www.theregister.com/2024/12/03/windows_mail_calendar_support/
[13] https://learn.microsoft.com/en-us/microsoft-365-apps/outlook/get-started/guide-product-availability
[14] https://www.coca-colacompany.com/about-us/history/new-coke-the-most-memorable-marketing-blunder-ever
[15] https://www.linkedin.com/posts/shanselman_not-enough-people-are-coloring-their-calendar-activity-7304707251548696576-SRfn/
[16] https://pubads.g.doubleclick.net/gampad/jump?co=1&iu=/6978/reg_software/applications&sz=300x50%7C300x100%7C300x250%7C300x251%7C300x252%7C300x600%7C300x601&tile=3&c=33Z-LhLkBn7zjH6q00VzEHUQAAA4I&t=ct%3Dns%26unitnum%3D3%26raptor%3Deagle%26pos%3Dmid%26test%3D0
[17] https://whitepapers.theregister.com/
Re: Point of pedantry
Yeah I remember all of this. In fact to me Outlook 97 looked like it was based on Mail and Schedule+.
What about Outlook (less shitty)?
ffs
Re: What about Outlook (less shitty)?
Like, perhaps, allowing the account username to be different to the email address for POP3/IMAP/SMTP servers. Without needing to find the route to get to the old settings UI?
Re: What about Outlook (less shitty)?
I'd take any version with proper integrated and GPO'd signature management to be honest.
Jumping through hoops to do very primitive signature management is a nonsense, and having to have something like the very-expensive Exclaimer to handle it all just for a SIMPLE MAIL CLIENT FUNCTION is ridiculous.
Slower and harder to use
Sure things about MS products;
New only means more buttons.
Cloud means slooooooower. Slow to open files, slow to save, slow to close.
How many sub versions of outllook do you have in your environment, yeah, that's not right.
If MS would stop building on the same csv and cmd back bone (now called excel and powershell) as they have for the last 40 years - and actually innovate,,,, never mind.
"Baffled by the plethora of Outlook options out there?"
No, I haven't touched Microsoft's shit in years and years.
Bwahahaha
Security
Security would be tightened considerably if every character I typed wasn't pushed, filed, stamped, indexed, briefed, debriefed or numbered by the OS I run at work.
Remove all the MS telemetry hooks and my data would be perfectly secure thank you very much.
Microsoft's myopic view of the world, their marketing horse dung and their product line does nothing for me anymore.
Re: Security
I would give you "Six" thumbs up for the reference, but one will have to do.
Re: Security
So Nadella is just another Number Two.
Re: Security
I'll give you half a dozen for the other.
Be seeing you.
To hell with a/the new version
How about you add some useful features instead? Like, IDK, how about when I setup a calendar event marked as "all-day" and "out of office" that you let me configure an automatic email message as part of the calendar event so I don't have to do that separately and manually? (Seriously, how is this not an option in 2025?)
Coke Analogy
No matter which version of Outlook you open it's not so much Coke Zero or Caffeine-Free Coke as New Coke.
Baffling
Nobody does baffling quite like Microsoft.
They’ve perfected the art of giving things the same name but wildly different functions. Teams (Work) vs. Teams (Personal)? Cheers for that. A “Microsoft account” that might mean your Hotmail login or your work credentials—depending on the weather, presumably. Outlook behaving completely differently on Mac and Windows. It’s chaos by design.
Then there’s the branding circus: Microsoft 365 Personal, Microsoft 365 for Business, Office 365 rebranded as Microsoft 365, and now we’ve got Microsoft 365 Copilot. It’s like a game of corporate Buzzword Bingo.
But here’s the thing: they’re not just clumsy—they’re strategic. There is a plan buried in all this mess, even if it’s a terrible one. It’s never about what users want or need. It’s about funnelling us into whatever corner suits Microsoft best. Push Copilot, push Edge, quietly break the old stuff to make the new stuff look better. Outlook (Classic) has felt noticeably worse ever since the push toward Outlook (New). Coincidence? Doubt it.
They’ve been gaslighting us for years—adding friction, removing features, and slapping on higher price tags. But now, they’ve outdone themselves!
With Windows 11’s absurd hardware requirements, they’re about to send millions of perfectly good PCs to landfill. Just like they did with XP. It’s irresponsible and unsustainable. Why not offer a lightweight version of Windows 11 for older machines? Strip out the fluff, keep it secure, and let people carry on using their devices. It can be done—they just don’t want to.
Because pushing shiny new hardware is always more profitable than doing the right thing.
Re: Baffling
They all do it.
Apple TV - A hardware device that connects to your TV and plays media
Apple TV - An app that runs on some TVs that emulates the functions of the hardware Apple TV
Apple TV - A Netflix-style TV streaming service (that may or may not be streamed to an Apple TV hardware device or app - see above)
Apple TV - An app for smartphones and tablets (both Apple and Android) that is used exclusively to stream the Apple TV streaming service.
Just to be clear; the Apple TV app that can used to stream Apple TV is not the same app as the Apple TV app that runs on some TVs that emulates the Apple TV hardware (although it can also be used to steam Apple TV).
I'm glad we got that all cleared up.
Re: Baffling
But when you stream Apple TV (as a subscription service) it's Apple TV+. Clearly.
Re: Baffling
The Day Of The Outlook!
The Doctor: We should point out that at this moment it is a fairly terrible plan.
Ten: And Outlook (Classic) almost certainly won’t be able to work.
The Doctor: I was happy with “fairly terrible.”
Ten: Sorry, I was just thinking Outlook (New).
Re: Baffling
I'm still using Outlook 2010 and Word 2010 and they are still working so much better than the current "updates" - I've bought the current updates but they are not as easy (or fast) to work with everyday.
Well, they could...
...allow it to handle rich media, encrypted between users in e-mails, storing data on their own systems, switching the display to a social media feed and they would have a free, largely distributed social media network working within an e-mail client. Then they could give users the option to see offers of interest to them (monetising it) and allow them to pick and choose the posts they see off their own bat or using a group filter. Then they would have a better social media network than anyone else. Near zero overheads as no centralised servers, bandwidth requirements or possible content censorship, with a fat revenue stream from user requested advertising and happy punters, sharing what they want, only seeing what they want, controlling their feed and their own data.
But this is Microsoft, so you'll just get a shittier version of what you had with fewer options that stores your data on someone else's system and falls over when they update it.
mutt -- it sucks less.
mutt:
"All mail clients suck. This one just sucks less."
Re: mutt -- it sucks less.
but it doesn't work with Winders
Point of pedantry
Pedant Alert!
There never was an Outlook '95. It first shipped in '97. Prior to that we had to use either the Microsoft Exchange Client or Microsoft Mail and Schedule+, depending on whether you were on Exchange or Mail as your backend. Neither of those supported POP3 - the distinguishing feature of Outlook was that it could support multiple backends.
I think '98 came fairly quickly, as '97 was quite buggy. It was also given away on a lot of cover CDs as Microsoft wanted to keep people in their ecosystem rather than use, say, Netscape's mail client for their POP3 connections.