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Outlook 2016 vs Mac Mail - which do you prefer and why?

I do not like the interface of mail, I use outlook. I try to go to different mail programs but always go back to outlook. I use it on my phone and ipad also. I got postbox 4 in a bundle one time and prefer it to mail, but still prefer outlook to all of them.
 
I wanted the same app on all of my devices, iOS and Mac. I was perfectly fine with Mail for years, but I didn't really use email very much. Then I started a degree and needed to add attachments a lot, often PDFs.

There is one thing that absolutely killed Mail for me. I don't know if it is still like this (but I suspect it is), but attachments that go in the body of the email. I wanted it like Outlook where an extra line would popup near the top that would hold the attachments. I didn't want to embed my PDFs or images, nor did I want them to appear as idiotically placed icons in the body. I understand if some people want to embed directly, make it an option though. Actually I think the embedding is an option, but the other option is simply an icon of the file.

Maybe it is OCD, but this rankles me like crazy, I hate it so much. So, I switched to Outlook because I could have it on all of my devices and the iOS version is really quite good.

The Mac version is not slower than Mail, from my experience. Now, I understand many people say Outlook has all kinds of features they aren't interested in. I agree. I still use iCal (or Calendar), but I love Outlook for email.
 
campyguy said:
IMHO, there's no comparison of the two applications. Mail is an email application, Outlook is a PIM - they're different applications altogether, with Mail offering a subset of Outlook's features. I use both, for different reasons.
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A personal information manager? Umm...no...Outlook is most definitely primarily an email client. Sure it has PIM features in it but how is not the same application as Mac Mail? They're email clients. Every email client has personal information management features in them.

Not trying to dog you or anything just curious how you came to that conclusion.
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Mencelus said:
As it says above, which one do you use and why? Like, I've used Mail for a long time, and it's okay; quite functional, no real issues with it. I recently have access to Outlook for Office 2016, and...it seems okay. I guess. I don't really know what the differences are, and online reviews are sketchy at best as to differences. So, I'd like to ask my fellow Mac users, which one do you prefer, and why? Bonus if you use the mobile versions on iPad or iPhone (which i suppose I would; I'm the sort of person that likes to use the same set of apps on all my devices, if possible).
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I've primarily used Outlook (formerly Microsoft's illegitimate child, Entourage) through most of my career. I've gone on stints here and there playing around with Mac Mail, but IMHO Outlook is way more user friendly in an office environment/professional setting.

The few things that turn me off of Mac Mail is the original message attribution. In Outlook, replies and forwards both include the full attribution including date/time stamp, TO: recipients, CC: recipients, subject, etc; whereas in Mac Mail, you only get that full attribution on forwarding. Please correct if this has been fixed since.

The other thing is the attachments - they're odd to me in Mac Mail. They show up within the body of the email either as an application icon or quick previewed. Outlook seems cleaner to me just showing an attachment bar at the top.

The only other thing is how message threads are shown in Mac Mail. It's like a bunch of blocks of emails. I prefer Outlook's grouped Conversations to the way Mac Mail does it.

Again this is obviously all preference so take it how you will.
 
I really like outlook but it need some love to add new and innovative ideas, which I guess I can create rules for if I really wanted. The calendar showing travel time would be a good start.
 
aross0531 said:
A personal information manager? Umm...no...Outlook is most definitely primarily an email client. Sure it has PIM features in it but how is not the same application as Mac Mail? They're email clients. Every email client has personal information management features in them.

Not trying to dog you or anything just curious how you came to that conclusion.
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Outlook has a calendar, contact list, and task list that I use every single day, and I use it with Excel and Word every single day - on both OS platforms. I own and use Exchange Server and two Office 365 accounts. With the relevant accounts, Outlook is a PIM - and I run two small businesses with Outlook as a tool to keep them running smoothly. It also works reasonably well with Outlook Cloud Services (Outlook.com). Simple as that.

Nobody I know uses Outlook for just email...
 
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BrianBaughn said:
AFAIK, the only free cloud service (for individuals) that will sync calendars with Outlook is a (new) account at Outlook.com.

Google calendars work just fine with the Mac's own Calendar app.
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How does Outlook 2016 handle gmail? Older versions required all kinds of tweaking to let it work at all . . .

As I use google for "cloud" email and calendar, and manual sync of contacts (sorry, not getting those google), Outlook doesn't seem to do it for me.

That said, I've always prefered the useability of Outlook to apple's apps . . . but it's a non-starter with cloud services limited to outlook.com
 
My workplace has recently migrated to Office365, for Outlook etc.

Whereas my mail still works through Outlook on my Mac, iPhone and iPad - and calendar, contacts etc. still get pulled in correctly to the various native apps (and 3rd parties - Fantastical etc.), Mail.app has simply given up the ghost.

Timeouts on trying to connect, and as a result, mails downloaded only up and till the end of October, when the switch was made...

My first option would presumably involve removing the Exchange account in its totality (from Preferences/Accounts), and setting it up again?

When trying to remove it from macOS, I am given the choice of removing the account from all devices, or only locally, on my MBP.
Being conservative initially, I opted for the latter. This doesn't really do anything, other than making the account "inactive" - so it looks like it is all or nothing.

My biggest fear about going all in, is that I might not get it syncing again - which would be quite problematic.

I'm happy using Outlook on my Mac - but the primary reason I would like to get the functionality going in Mail.app, is due to my MailActOn and MailTags plugins, which offer some very useful features. That, and the ability to archive my Outlook mail account into Devonthink Pro Office, with all its many benefits...

Anyone experience a similar issue? Any suggestions? Should I just give it a go, and remove all, and hope that the re-introduction of the account will fix things?

[EDIT:]

Just checked DTPO again, and never realised that it now/always(?) supported mail account archiving from within Outlook as well - which I'm now doing. If it works as is hoped, then that's a big concern taken care of. Would still be useful to have MailActOn and MailTags hit my Exchange account in Mail.app, but at least one issue has been resolved satisfactorily.
 
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Le Big Mac said:
How does Outlook 2016 handle gmail? Older versions required all kinds of tweaking to let it work at all . . .

As I use google for "cloud" email and calendar, and manual sync of contacts (sorry, not getting those google), Outlook doesn't seem to do it for me.

That said, I've always prefered the useability of Outlook to apple's apps . . . but it's a non-starter with cloud services limited to outlook.com
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Looks like current flavour of Outlook (for Mac anyway) for most users still does not play nice with Gmail. I understand that if you are on the Suite's fast track (as far as updates and trials are concerned) and a 365 member, it is possible to get it to work - with a promise that lowly Others will get it later this year.

While I've often found myself using it at work sites as a freelancer, I really don't find it intuitive enough for me use as my personal SOHO all-in organizer on my own Mac. It would be great if Apple had an equivalent to it - they have all these sync options thru iCloud, but all to different apps. As it stands right now, I use the standalone apps on my Mac and iPhone - with the addition of Outlook on my phone for the occasional use of adding attachments, because the iOS Mail app lags there. But just use Mac Mail app otherwise...
 
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