Microsoft's many Outlooks are confusing users – including its own employees | Hacker News Reader

Microsoft's many Outlooks are confusing users – including its own employees

theregister.com

81 pointsrntn88 comments

Around our office... we have what seems to be a 50/50 split of users on the "old" Outlook and the "new" Outlook.

Many users have tried the "new" Outlook and found it different in unexpected and confusing ways - and being a business app, they just want to get stuff done so they go back to what they know.

I forced myself to stick with the "new" Outlook, and while it still continues to surprise me in confounding ways, it's grown on me a bit. I still find many buttons/options unintuitive to use or find. Finding a way to just see my unread emails took me way longer than I care to admit, and I typically am one to figure out UI's fairly fast.

Having both the "old" and "new" Outlook installed side-by-side is also adding to some of the confusion. It's far too easy to go back to the old version, even by accident. Although, this seems to be inline with other Microsoft endeavors, such as Settings + Control Panel, et al...

> I still find many buttons/options unintuitive to use or find. Finding a way to just see my unread emails took me way longer than I care to admit, and I typically am one to figure out UI's fairly fast.

Switching _to_ outlook is like that. Got a job in a non-tech company a few years ago and I still have trouble with the unintuitive and odd behavior that is outlook classic.

Switching from the “New” ribbon to the “Classic” ribbon in New Outlook (adding labels to the icons) pretty much solved it for me

I've also attempted to live with the New Outlook on a work laptop while keeping the Old Outlook going on my work desktop.

The new interface looks nice, but it does take a bit to re-learn where things are. Most things I do regularly are there, but the more occasional things I have to search for. Irritating, but that's just part of software upgrades.

Attachment handling in the New Outlook is extremely frustrating. Users cannot save a file to an arbitrary location on their machine - it's OneDrive only. If the attachment is a file Office knows what to do with you do get the option to open it in <Office App>, but only after it uploads the file to OneDrive. Often the app won't launch, so you're still stuck trying to figure out where (if) it saved the attachment.

You actually don't even get to pick where in OneDrive the file goes, so they get dumped in Documents or wherever Outlook decides makes sense.

In a hurry and just need to save an emailed PowerPoint to your desktop so you can get it on the screen quickly? Too bad.

Got a lovely organization system for a type of .csv that gets emailed daily? Well, you can't save directly there anymore.

I'm not aware of an email client since Pine where users couldn't arbitrarily choose where an attachment goes.

This is a software designed to specifically lure you into an MS ecosystem, not a revolutionary new thing driven by technological improvement. You are pretty much already caught if you use Outlook for that matter, but the new version puts their cloud services on the table and severely nudges you to use them.

Team planning in outlook are quite nice, but there are better mail clients. Of course the usual domain integration is worthwhile as well, which probably was the success story of Outlook.

Say what you want about Apple, at least somewhere in the org they have people both able and willing to say “I don’t care why you think it’s necessary, that’s stupid and confusing and you’re not doing it”.

Whereas at Microsoft apparently when someone proposes 6 different apps with the same name, whoever should say no just raises their hand with a thumbs up without looking up from their phone.

There are four, possibly five distinct products called "Apple TV", including hardware, software, and a service.

Apple TV : device that connects to your TV

(Apple) TV app : program that lets you access video media sold by Apple and other streaming services that let Apple index their media (which is all except Netflix)

Apple TV+ : subscription service to access video media produced by Apple

While not the most clear situation, it’s not too bad, in my opinion.

The way you described TV app and Apple TV+ makes it sound that they are identical or am I missing the difference?

I edited it to make it a little more clear, but I can see the confusion.

Apple sells media that others produce, but they also sell subscription only access to media that they themselves produce.

So movies and tv shows that you “buy” (really, rent for as long as Apple allows you to access it) can be accessed via the TV app. Basically, the stuff where Comcast or Disney or Sony or Warner Bros gets paid 70% and Apple gets a 30% commission.

But for things Apple directly produces (or buys and then re-sells), they require customers to pay an ongoing fee for Apple TV+.

Also, LeoPanthera is right that the TV app can also be your library for your own files that you import, and then you can synchronize that to your phone or iPad’s tv app.

The TV app also plays local video purchased from the iTunes Store (which still exists) or imported by the user.

For the other apps that support the special API, it can also be a portal to jump straight into their content. Depending on your region, Netflix, Disney+, and Amazon Prime might allow that.

You access your Apple TV+ subscription via the TV App lol.

How do you explain iOS' settings app then?

And once every iOS user was sufficiently confused about their settings, to the point where they where afraid to touch the settings app, out of fear that they might change something and never be able to figure out how to change it back, Apple replaced the macOS settings app with the iOS one. Thereby allowing desktop users to experience the hardship and mind numbing confusion that is the iOS settings app.

I hate settings on iOS so much. What a horrible broken shitshow that is.

The only way to use any Apple settings app now, IMHO is to search for what you want. Even if it's something you have visited countless times before it's faster than squinting at the long, long column of tiny icons. I miss the big friendly grid of icons so much.

Is this interface that much different from "classic" OSX preferences? The old panel with horizontal icons was replaced with sidebar tree which loads sections withouth need to return to main screen - that is pretty much convenient.

But I do agree - settings panels not only in OSX become too complex and often featuring stuff that should stay on mobile devices. It's been years but I'm still not fond of all sorts of notification centers and destkop applications being able to nag you with their stuff.

On top of the list vs grid, it was reorganized into multiple layers, universally understood controls were replaced with new ones never used on macos before, universally appreciated design elements like containment boxes were removed, native controls were (at least in some places) replaced with web-based look-alikes, recognizable ucons were replaced, decades-old terms were replaced...

I genuinely don’t understand this sentiment. It seems perfectly fine to me. I can understand how a non-technical user would get confused, but I appreciate the granularity.

My mother-in-law came by, her phone has switched to "dark mode", because she accidentally did something in settings. There is no way for any regular user to find out that that was not what had happened. She accidentally switched an accessibility feature, but you have to know that that is a thing to even begin to locate it and there are multiple feature that does something similar.

The granularity isn't the issue, the discoverability is.

I have a hard time understanding this.

I can agree that things in macOS/iOS settings may be broken or unintuitive or whatever (I have no examples but I'll believe you).

But a shitshow? No. Window's Control Panel is a shitshow.

What I'd like to know from you is, if macOS/iOS settings isn't the closest thing to perfect, what is? My Gnome settings control panel on my main desktop is a certified shitshow. But macOS/iOS? Nah

The old macOS settings wasn't perfect, but it was much better. On iOS, I don't know, I think it's just a very hard problem. iOS has a ton of settings, but honestly the only way to fix the settings app on iOS is perhaps to start removing features.

Admittedly the iCloud section is confusing, otherwise it's the least worst OS settings app I've seen.

Well, there’s only one settings app at least, which is also different than what Microsoft does.

I had no idea iOS had Settings (New), Settings (Classic), and Apple Preferences - all competing for user share just like Outlook (New), Outlook (Classic), and Windows Mail are.

Un-sarcastically though, you're also describing the windows 11 settings pane. Which arguably has settings (new style) control pannel (old style) and various *.msc management consoles for managing things like users and local security policy

As I comment from my iPhone XR Plus Air Max Ultra Extreme, it always annoyed me the 3rd generation of the iPad was officially named "the new iPad" in 2012, replacing the iPad 2.

I have "the new iPad" in a drawer, but its last software update was released in 2016. It's not very "new" anymore, but that's its official name.

How cute, you think Apple cares about the steaming pile of shit Mac OS is.

What is Microsoft aversion to their "classic" Outlook? I never understood why they didn't just bundle that version with Windows. They've always attempt to foist an inferior version upon home users, starting with Outlook Express.

And why rewrite and push a new inferior version to users who already paid for the "good version". This is a tools that millions of their users rely on to do their job every day, it's extremely unprofessional.

Well, for one thing, classic Outlook's HTML rendering engine (to the extent it's even an "HTML" rendering engine instead of a Word document rendering engine) has some fairly radical divergences from standard HTML/CSS behavior. For those of us who have to generate HTML e-mail for whatever reason, it's distinctly unpleasant.

That might not be enough reason in and of itself to throw out the whole application, but I sure won't miss that one part of Outlook.

Well, older versions of Outlook actually used MSHTML/Trident as a render engine: the engine of Internet Explorer.

They could, if they want, use WebView2 - embedding MS Edge.

While I obviously don't know, I'd guess that they could plunk in Edge/Blink and call it Outlook 2025.

I suspect a bunch of technical debt - the core of the application dates to 2000 or before (there are menu's changed for a very very long time).

Does the design need to change to address technical debt?

First version of Outlook was Outlook 97.

It was supposed to be Outlook 95 and ship with Office 95, but the app was late.

I feel like at some point Microsoft deliberately decided not to want to maintain "old stuff" anymore. You see this with many other products as well. Desktop is bad, web is good.

Microsoft is moving away from the single-platform; they want their apps to run on Windows, web, Mac OS, iOS, Android, and maybe even Linux. They do not want to maintain radically different versions for all these different platforms.

Yes, at the cost of the desktop experience - it seems. And at the cost of customization.

The desktop experience has been secondary for years now -- Microsoft is only now catching up to that trend.

They shouldn't. Microsofts most valuable users are on desktop.

I'm not so sure. Desktop, particularly Windows, is definitely important, but mobile is used a ton even in business.

Microsofts tools obviously needs to work well on mobile, and I can understand not wanting to maintain multiple code bases, but I think their hurting their users by not doing it.

I know at least one CEO who will absolutely explode if they fuck up his Outlook. He probably have 20 years of business correspondences in there. Is that a good idea? Probably not, but he does. If Microsoft mess up Outlook, then there's very little reason for his company to not look at Google and Gmail, and he probably will just because he'll feel like Microsoft screwed him over.

Outlook Express is still a much better experience compared to the new Outlook.

I believe it has a lot to do with the fact that new Outlook operates on email in their cloud, and that means they can … process your email as they see fit.

Remember that adding an account to new outlook means all your email gets uploaded to O365 servers. It no longer interacts locally. That includes external services like Gmail etc.

I’m using the new Outlook. It’s generally fine, although my biggest issue with it are infinite loading screens. This is a desktop e-mail client, it should not require an Internet connection to show e-mails, especially recently received e-mails.

AFAIK this is because it's not really an email client. If your company uses an email server instead of hosted Office 365 email, setting up New Outlook with it will send your server's IMAP details and login information to Microsoft's cloud. Their cloud then acts as an IMAP/SMTP client, and every email you send/receive gets proxied through Microsoft's servers. I'm not sure why they decided to do things this way, but it means I'm never going to switch to New Outlook.

My company is using hosted Office 365 e-mail.

Their trick with server-side IMAP is well-known, and makes some sense for the Outlook mobile apps. But it does not excuse not having recent messages cached.

So New Outlook won't even work on a network behind a DMZ?

nope-o. It's a webview with extra spice.

I remember hearing around 2004 that from watson/microsoft telemetry Outlook was the most ran app in the world by the hours being up. Certainly made sense because it was always on for everyone, including myself. The things one could do in Outlook with rules, highlights, actions, views, and (for a while at least) custom forms was absolutely limitless. I did a bunch of MAPI coding too which gave me a lot of appreciation for the underlying API. The regression to the "dumber" client (and lack of support for offline PST!) is not great.

"Classic" Outlook has gone to hell in the last decade, too. Outlook 2010 was "peak Outlook". It was fast and worked well. Armed with "Advanced Find" and a large but poorly organized mailbox I could find what I needed quickly and efficiently. The whole "de-emphasizing" of the Advanced Find feature and moving to that god-awful unified search box was emblematic, to me, that the adult supervision had departed the product team.

I enjoyed making MAPI forms to do automation in my office, back in the day. MAPI and custom forms never reached the level of Lotus Notes application development. This was, arguably, because Notes was actually a general solution that just happened have an email client implemented in it. Outlook was an evolution of the old "Exchange" / Microsoft Mail paradigm and was really a mail client at its heart.

There was a period where this confusion was there with Teams (Classic) and Teams (New).

There was the whole .NET Core/.NET (while having .NET Standard for libraries) confusion. Even now many people think .NET requires Windows. Maybe they should have named it .NET Open?

I won't copy/paste the comment, but awhile ago I ranted Microsoft product naming and got some nice replies: https://news.ycombinator.com/item?id=40419292

Or when they renamed Lync to Skype for Business, which had nothing to do with Skype.

And then they have OneDrive, SharePoint, Office365, and Teams as ways to share files... which are all the same thing/infrastructure under the hood.

Missed opportunity to name it .ORG

The confusion persists in job requirements, especially when those requirements are translated from technical stakeholders through HR.

What confusion? "x years of .NET experience" is what I see and it should suffice unless your whole career has been in an archaic version of .NET framework then you should have no issues working with either.

Do they just not let marketing into the important meetings? Naming isn’t a solved problem but marketers are usually pretty good at knowing when to avoid confusing situations like these.

In my experience Marketing causes most product and feature naming issues. Technical folks want to name it something obvious, and marketing overrules them.

CoPilot takes the crown of most overused moniker now.

Being a Thunderbird user, I feel as though I've missed out on a critical development in tech history.

I feel like the most important factor is UI consistency. If the UI changes, it costs so much time and re-learning.

Thunderbird has mostly been the same since many years. The only thing I noticed is, that the quick search has become buggy and scrolling in the inbox takes a second to load the titles.

I'm 4 years into having to use outlook after switching jobs and no longer being able to use google workspace. I continue to be frustrated by the confusing and arcane processes required to do basic stuff like fine previously declined meetings, book an out of office that doesn't spam everyone, use search and actually have it find stuff, automatically place emails into folders in a sane fashion, actually accept/decline a meeting and not have it randomly stay as "tentative" and so on.

Comparatively, outloook feels like a complete mess.

Haha, today I searched for some emails.

It put some really old ones in a the top as the most relevant. Then in a section titled "Older" it put the most recent ones. The sort column was by date.

> use search and actually have it find stuff

There has never been a good first-party answer to that in the past, though there were various third-party extensions and tools. Today the answer is just add the copilot license to your o365... its automatic rag over all your stuff is better than anything available before.

Microsoft's everything is confusing...

Last time I had a corporate-y job, everytime someone would send me a spreadsheet it would open on Office365 in a webview within Teams instead of simply opening in the Excel desktop application... Why? No idea. Everything was Windows and MS everything, you'd think it'd be integrated but no. Like, I never had any idea if what was shared with me would open in the browser, Teams, native app, etc... Syncing was horrible.

Definitely not a surprise to hear that there's multiple Outlooks confusing people.

Being able to open a file from Teams in it's native app is actually a feature that's locked behind a particular licensing tier. I believe it used to be available under a Microsoft 365 Business Standard or Premium license, but now you have to upgrade to an Office 365 Enterprise E3 or E5 license to be able to open it in the native application you already paid for. Microsoft's licensing structure is a special kind of nightmare.

Hahaha of course it is... Thankfully now I'm out of corporate jobs and doing my own thing so I can use the tech I want. Which means no MS anything.

> everytime someone would send me a spreadsheet it would open on Office365 in a webview within Teams instead of simply opening in the Excel desktop application.

This bites me on a regular basis. It's incredibly annoying.

Microsoft Outlook has a bug when you click on the notification after you receive an email, it opens it behind other windows. [0-2] It drives me mad!

[0]: https://answers.microsoft.com/en-us/windows/forum/all/email-...

[1]: https://answers.microsoft.com/en-us/outlook_com/forum/all/cl...

[2]: https://answers.microsoft.com/en-us/outlook_com/forum/all/ne...

What is the email app equivalent to VoidTools 'Everything'. Blazingly fast with no wasteful focus on UI design concepts like ribbons, color palettes, etc. Just full effort to have the fastest search algorithm possible with async streaming of results to the UI and all efforts placed on searching/filtering/tagging,etc.

The Bat! is a Windows client that focused on those things to a large extent. However, the fact that RitLabs are based on Moldova gives me pause. It did have MAPI support, so it was somewhat workable in company situations which used Outlook.

A blast from the past. I used Bat! around 2003-2005 and didn’t even know it exists anymore. It was awesome, now I want to check it again.

+1 for The Bat! been a happy user for over 2 decades

more info: https://en.wikipedia.org/wiki/The_Bat!

What's wrong with Moldova? People there wish they were part of the Occident proper more than your median USA voter.

eM Client. The best one I've found so far.

https://www.emclient.com/download

If you use any third party product that uses the Microsoft account for logging in, it's an educational experience to just have the network tab open when you log in and count the distinct, Microsoft-owned domains that the login process will cycle you through.

There are companies that keep their products' infrastructure in separate siloes; there are companies that manage to merge everything into a unified architecture - and apparently there is Microsoft, that makes sure each of its products has to talk with every single one of its other products to get anything done.

Classic microsoft. Too many competing products and not enough integration.

I only know of two though? (on PC)

There's the native Outlook desktop client, the "classic" one, that's only semi-miserable and does kinda work, just feels ancient.

Then there's the web client, available from both the browser and as the "modern" desktop app. It's the same thing.

Are there others I'm missing? No, the Windows builtin Mails app is not Outlook.

Microsoft might be the first company to actually address covert channels, one only has as many accurate bits of data as is possible in the last 48 hours using 20% of the intended events, then it drops to a few bits per day in history.

Everything about Office 365 (now called Microsoft 365 for some reason) is extremely confusing to me. It's not just Outlook, there's like 3 versions of the other apps as well.

I have never liked Outlook's various programs and only use the mobile app and the online variant on desktop. Which isn't perfect, but more attuned to Gmail.

Whoever thought this was a good idea should step down.

Let me know when we can remove "RSS Feeds".

Microsoft has been SO bad at this for ages. It is clear that they are actually a company consisting of thousands of smaller companies all competing for different things. There is absolutely zero cohesion and they are fortunate to have a monumental base of users who are forced to tolerate their bullshit.

Can you reorder folders in New Outlook yet? No? Okay, I'm sticking with old then.

You can try to reorder them. Whether or not it remembers the setting is another question.

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