Microsoft Outlook, the stalwart all-in-one Mail/Calendar/Contacts app for Mac (and Windows), designed foremost (but not exclusively) to work with Microsoft Exchange servers, has been around approximately forever.
Many still use it, and even though I no longer do, I’ll be the first to recognize it has powerful capabilities that no other email program for Mac, or Web-based system like Gmail, does. There’s also something to be said for its single-window integration of mail, calendar, and contacts; it just fits some people’s workflow better.
Anyway, Outlook for Mac is old, with code roots going all the way back to Entourage in 2001, and before that Outlook Express in 1998, and it’s probably full of twisty code that’s hard to maintain, and it has some performance limitations that are probably hard to fix. So, Microsoft has decided they’ve had enough, and they’re pushing out an all new Outlook to replace what they’re charmingly calling “Legacy Outlook.” (Computer companies call something “legacy” when they wish they no longer had anything to do with it. I’m just going to call it Classic Outlook.)
If you’re an Outlook user who does not host your email at a third-party Exchange provider like Intermedia, there’s a good chance you’ve been switched already. (They don’t give you an option. They just do it, and then leave it to you to switch back if you don’t like it. To switch back, you choose “Legacy Outlook” from the “Outlook” menu in the upper left.) If you are hosted at Intermedia or similar, they have to leave you in Classic Outlook, because New Outlook supports every kind of mail system except Microsoft Exchange when provided by a third-party host.
Not too surprisingly, New Outlook feels a lot like Web Outlook. And while its performance is indeed zippy — which was always a problem with Classic Outlook — it comes with a lot of limitations compared to its predecessor, and I don’t expect some of the more powerful features, such as Advanced Find, to ever be implemented. It’s awkward with handling “On My Computer” mail (which I generally try to discourage the use of, but there’s a lot of it out there, and sometimes with good reason), its search is so-so, etc. It’s ok. You might like it better, because it’s more responsive and it might cover what you need. You might also find yourself in it, and asking yourself, “Where’s all my stuff?” because it didn’t move you seamlessly. I get this a lot.
But if you don’t like it, you can always switch back. Just choose “Legacy Outlook” from the Outlook menu. And if they force you into New Outlook again, switch back again. They always ask you why you’re switching back, so make sure to write something like “it just sucks” or “I don’t like change” or, perhaps, even something constructive. Or just switch.
As a technical person, there’s some bummers I have found with the new version — such as the fact that there’s no real way to back up your local copy of whatever’s on the server, like you can with Classic Outlook. The assumption is that the server is always right, and therefore you can always reload from the server. I know from experience that the server is not always right.
Another drag with New Outlook is that in Classic Outlook, it is possible to maintain separate “profiles” for users. This is an amazingly useful troubleshooting tool, as it makes it possible to keep one mail account in one profile, and another mail account in another, to isolate problems. New Outlook could have kept this setup, and quite easily, since the profile mechanism is still in place; but, for whatever reason, New Outlook keeps account information outside of profiles. So, you can make a new profile, but what happens is New Outlook sees “oh, this account has no mail downloaded for it, let’s do it” and it will just download mail for all accounts you have configured. This effectively renders profiles useless. Maybe most users won’t care, but I do. Especially when I’m trying to help solve a problem you’re having.
Using Classic for as long as possible
Why do they keep Classic Outlook around? Well, they may feel like New Outlook ain’t fully baked yet, which is entirely true. But, there’s a whole additional story — way back when, like, when BlackBerries were a thing, Microsoft sold their Exchange Server software for companies to run and manage themselves, and some hosts like Intermedia emerged so you didn’t need to maintain your own Exchange server in your office. But then Microsoft started offering hosted Exchange themselves, at much lower prices than the third parties could afford to, and the writing was on the wall.
Microsoft now offers hosted Exchange as part of Microsoft 365, and that’s what they want everyone using. While they haven’t quite yet killed off “on-premises” Exchange, which is what a host like Intermedia uses, they have made it much more expensive to run, requiring ongoing subscription fees to Microsoft, naturally. The path forward for Intermedia and other companies offering hosted Exchange is to instead become Microsoft 365 resellers, and indeed these companies already have those offerings, and their salespeople are already calling me trying to get customers to switch. At some point in the next few years, Microsoft will likely stop offering on-premises Exchange at all; they’ve essentially put companies and hosts still using it on notice. I’ll worry about switching their customers then.
Anyway, this all makes me think Microsoft can’t quite get rid of Classic Outlook just yet, if you want to keep using it, because until New Outlook supports on-premises Exchange, they have to provide Classic Outlook for all the businesses that depend on it. And they may not want to ever put in the effort into making New Outlook work with on-premises (or third-party hosted) Exchange, because they’ve already got it working with their own hosted Exchange at 365, and they’re clearly going to cut off on-premises (and third-party hosted) Exchange at some point.
But what wouldn’t surprise me is if at some point in the future, Microsoft simply forces use of New Outlook unless you’re in the relatively unusual situation of using third-party hosted Exchange, and then they’ll let you use Classic Outlook. At that point, you can be sure I’ll be looking for a trick to still permit use of Classic Outlook. Also, when that day comes, there will be some final version of Classic Outlook, like 16.108.1 or whatever, and there’s no reason to think it won’t continue to run for years more, until some future version of macOS breaks it, if that even ever happens. Some old software runs for a very long time. You just have to make sure you keep a copy so it can be reinstalled in case it gets accidentally updated to a newer version that forces New Outlook.
Anyway, if Microsoft puts you into New Outlook, sure, try it out if you like, but if you don’t like it, remember you can switch back. Choose “Legacy Outlook” from the Outlook menu.
Image by brittgow courtesy Flickr Creative Commons