Everything You Need To Know About Outlook For Windows (Deployment, Architecture, and Update Playbook)

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This Week in IT, Microsoft is promising to support the classic desktop Outlook app until 2029, but not everyone is happy about the new Outlook for Windows. I take a look at the new app and whether you should consider using it or holding off for now.

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This Week in IT. Microsoft is promising to support the classic Outlook app until 2029, but not everybody is happy with the new Outlook for Windows. So I take a closer look at the new app and whether you should use it now or hold off.

Welcome to This Week in IT, the weekly news show where I talk about everything connected to Microsoft 365, Windows and Azure. But before I get started today, I’ve got a quick favour to ask you. About 60% of the people who watched last week’s video weren’t subscribed to the channel. Now as we go live today, we’re on about 3,590 subscribers, so I’d really love it if we could push that over to 3,600 this week.

So if you’d like to see these kind of weekly news round-ups and my analysis of the news, then please subscribe to the channel and don’t forget to hit the bell notification to make sure that you don’t miss out on the latest uploads. Now if there’s one thing that people get excited about more than browsers, it’s email clients.

This week Microsoft announced it was going to support the classic Outlook app until 2029, but as you’re probably aware, Microsoft last year made available in preview form the new Windows client for Outlook, which replaces the old mail calendar and people apps that came as part of Windows 10 and Windows 11.

Now this new client isn’t just designed to replace those apps, that’s kind of how this whole project originally started, but eventually it’s also going to replace the what I like to call big Outlook that comes packaged with the Microsoft 365 apps for desktop that you get, like Word, Excel, OneNote and all the rest of it. You also get this big clunky old classic version of Outlook, and I say old because I haven’t used it myself now for for quite a long time. So what is the deal with this? How is this going to affect people that currently use the classic Outlook app? And what are the problems going to be if you decide to move to the new Outlook client right now?

So first of all, nobody is forcing you at this point in time to use the new client app. It’s at the opt-in stage, so if you’re using the classic version of Outlook, there’ll be a little toggle button that you can switch and that will then install the new Outlook for Windows application and make that your default email app in Windows.(…) And that’s opt-in, as I said at this stage, nobody forcing it, but it’s going to move at some point probably later this year to what Microsoft is called in the opt-out phase. So it will become the default client for everybody when it’s generally available, and you will have the option to switch back to the classic Outlook if you want to do that or if you need features that are in classic Outlook that are not yet available in the new Outlook for Windows.

Then at some point in the future, you’re going to be in what Microsoft is calling the final cut-over stage, where essentially the new Outlook for Windows application is going to be deployed to everybody, but you won’t have the option to switch back to classic Outlook. Now that applies to new users and new devices if you like, but if you’re still at that point using the classic Outlook, Microsoft isn’t going to remove it, you’ll still be able to use it if you’ve already got it installed and that support, at least Microsoft is saying at the moment, will last until 2029.

So if you haven’t seen the new Outlook for Windows application, it essentially looks like Outlook.com or Outlook for Microsoft 365 in the web. So Microsoft is trying to make all of these different versions of Outlook work, look and feel more or less the same so that you’ve got a very similar user experience.

Now of course that’s where the classic Outlook app really differs at the moment because it’s something from the past and it doesn’t reflect what Microsoft has been doing in the web versions and now the Outlook for Windows app in recent years. So it’s designed to bring some kind of unity to all these different versions of Outlook.

It’s delivered as an MSIX package, so that’s the successor to MSI, the MSI packaging file format. Interestingly Microsoft is saying that the new Outlook for Windows is a native application. Now maybe that’s a little bit of a stretch of that imagination depending on how you define a native application. Of course like the big desktop apps like Word, Excel and I believe Outlook too, this is not programmed in something like C++ that’s considered a native application on Windows but it uses much like the new Teams client, Microsoft Edge WebView 2. So it’s kind of based on web technologies using a component that’s built into Windows and it’s actually portable so it works on the Mac and I think Linux as well although don’t quote me on that.

So native, not native, I guess that’s up for debate a little bit. Microsoft is saying that it’s a native application. I know that’s important to some people but what Microsoft is describing, how this integrates with Windows, it uses the native Windows integration component.

Now this is a small component that runs in the background, it’s updated weekly or more or less weekly using the Office content distribution network and basically it’s a thin kind of server component that sits there running and allows the new Outlook for Windows to integrate with Windows more deeply in a way that a web application might not normally be able to do. So things like file dialogues, getting all those kind of integrated experiences with the action center and notifications, that’s how Microsoft is able to achieve this.

Now these kind of rapid updates to the native Windows integration component, Microsoft is able to do because it updates that component which is the very small component sitting and running in the background but none of the features in Outlook for Windows actually are updated at that point. It doesn’t involve updating those features in the application itself but just in this service component that sits in the background.

So if you like, the application itself is the client, this native Windows integration component that sits in the background is the server and they’re loosely based on the same version. So while they may not update at exactly the same time, they shouldn’t be a million miles apart from each other in terms of version. Now Microsoft is saying if you have any problems with the two versions not working together, all you need to do is basically close the Outlook app and reopen it and it should automatically update so that the version number with the native Windows integration component is more or less the same and works, although I haven’t experienced any problems like that but I guess that might happen if somebody doesn’t close the Outlook app for a long period of time.

So if you’re familiar with how Outlook works on the web in Microsoft 365, basically you’ve got a pretty good idea of how the Outlook for Windows app works. The biggest difference I suppose is that it supports multiple accounts.(…) So with the app you can add not just your Microsoft 365 account, you can add a standard consumer Outlook account, you can add a Gmail account, I believe it supports Apple Mail.(…) So you can add your different accounts there and see them all in the same application whereas you can’t do that with the Microsoft 365 Outlook web client.

So while that’s a big advantage for people who need to work with multiple email accounts at the same time, there are a lot of features in the classic Outlook app that haven’t yet been ported to this new Outlook for Windows client and of course that could be a big issue if you’re using this at work. So the main things that you don’t yet have in the Outlook for Windows clients are offline support. There’s no support for those kind of classic COM and VSTO add-ins that are quite common in the classic Outlook app. So the Visual Studio tools for Office add-ins and the COM object add-ins, you can’t use those in the new Outlook for Windows application. There’s no support for EML or message files and no support for PST files and at the moment there’s no support for reordering folders or pop free accounts.

Also you can’t drag and drop emails or documents of the application to your Windows desktop at the moment. So while Microsoft is promising to include those features before it becomes generally available later this year, some of those things like PST file support and pop free support are not on such a clear timeline and Microsoft isn’t saying exactly when they will appear but seems to be committing to adding them. I’ve been using the Outlook for Windows application now I think for about six or seven months I came from the classic Outlook app and I’d like to share my experience with it. Now in my mind one of the biggest advantages of the new app is that it’s a modern look and feel.

It’s very similar to what you see in the web browser with Outlook and I think trying to you know create some consistency between these experiences is really important.(…) Now at work we use Gmail so I got to prefix this conversation with that disclaimer so of course the experience with Gmail is a little bit different from what you get with a Microsoft 365 account and the biggest problem I have using Gmail with it is in the calendar part of the application. There’s no support for adding Teams links when you create a meeting you want to make it a Teams meeting so that the link and everything is shared with the people who are going to attend.

Unfortunately at the moment I don’t know what Microsoft plans to do with this, that doesn’t work unless you’re using a Microsoft 365 account and of course because we’re on Gmail I’m not doing that so when I create Teams meetings I have to go back to Gmail in order to do that if I want to include the Teams link automatically there. So that’s a big problem in my mind of course that’s not going to be an issue if you’re using Microsoft 365 for your email.

Another thing that frustrates me about this is that you know Microsoft is trying to make this an experience that’s similar across all of the different applications and platforms and Outlook on mobile offers me a great you know way of viewing all of my email so that basically the inboxes from all the different email accounts that I have installed in that application are combined.

I can view them either separately or combined and the Outlook for Windows application at the moment doesn’t allow me to do that it doesn’t allow me to see a combined view of all my inboxes and I find that a little bit frustrating so I have about five or six different email accounts installed there and I have to go through each inbox individually to see any new mail so Microsoft please that really needs to change. Another big one for a lot of people it doesn’t matter to me so much these days although it would have done in the past and that’s that there’s no offline support at the moment.

Microsoft is promising to add that before it reaches general availability and I think that’s going to be a big thing for a lot of people. I know Microsoft likes to think that we’ve all got internet connections all of the time it’s like well hell I would like to be able to read my email and work with it even if I’m offline.

Again maybe an issue just with using Gmail with the new Outlook for Windows app and this has improved a lot over the last few months is that synchronization of things like calendar objects was sometimes quite slow and sometimes just didn’t work at all and Microsoft does seem to have ironed those issues out to be fair so I’m going to just put a little bit of hold on that one but you just be aware of that if you’re not using this with Microsoft 365 there are still a few little quirks. So what about the positive side well the first thing apart from the fact that of course you get this familiar look and feel which I think is great it’s a lightweight application the search is much faster and more reliable and I’ve had no problems with the application hanging or crashing which sometimes would happen with the classic Outlook.

Because it looks like Outlook on the web it’s simple to use it’s easy to pick up I don’t think there’s much of a learning curve sometimes the classic Outlook looks like a bit of a monster there’s so much there it’s not so intuitive to use but if you’re using the classic Outlook in your organization now probably the biggest thing to be aware of is there’s no COM add-in support.

No Visual Studio Tools for Office add-in support either the new Outlook for Windows is only going to support web add-ins Microsoft has said that right out of the gates there aren’t any plans at all to add support for com add-ins to the Outlook for Windows client in the future so there’s no sense hoping on that of course Microsoft could change their minds.

But I think technically it may be just not possible so whatever other applications you’re interacting with from Outlook itself they will also need to support this new web add-in plugin model for Outlook going forwards.

So, if you’ve got legacy applications that cannot be updated then obviously that is a potential issue for you with the new Outlook client for Windows so despite some of the dislike people have for the new Outlook clients personally I like it I think Microsoft is going down the right direction with the new clients have you used it let me know what you think about it in the comments below I’d love to know.

If you found this video useful I’d really appreciate it if you gave it a thumbs up because it helps us to get the video seen by more people on YouTube and to grow the channel I’m going to leave you with another video on the screen now where I talk about the new AI features coming to Windows 11 and Windows co-pilot in the moment 5 update for Windows 11 so do check that out but that’s it from me for this week and I’ll see you next time.