Switching from Gmail to iCloud or Outlook?

[Bromio]

Hello:

I'm a happy iMac owner and within some months I will be buying an iPad. I also have a laptop with Windows 8.1 and a smartphone with Windows Phone 8.1. So, because of the lack of syncing between Google services and Windows Phone (for example, push notifications aren't allowed unless you use Gmail app), I've decided to switch from Gmail to another mail/calendar/contact/tasks/reminders/cloud service: Outlook or iCloud.

I really can't choose one from another. According to the information I've got from the Internet, they both offer similar capabilities, but I don't know how they behave in practice. So, which one do you think I should choose? I want full sync between all my devices.

Thank you.

 

[impaler]

I think the best inter-device sync comes from picking ONE ecosystem and sticking with it. I'm all Apple, so iCloud works for me.

Hello:

I'm a happy iMac owner and within some months I will be buying an iPad. I also have a laptop with Windows 8.1 and a smartphone with Windows Phone 8.1. So, because of the lack of syncing between Google services and Windows Phone (for example, push notifications aren't allowed unless you use Gmail app), I've decided to switch from Gmail to another mail/calendar/contact/tasks/reminders/cloud service: Outlook or iCloud.

I really can't choose one from another. According to the information I've got from the Internet, they both offer similar capabilities, but I don't know how they behave in practice. So, which one do you think I should choose? I want full sync between all my devices.

Thank you.

 

[Primejimbo]

I have both and I'm stating to like outlook more and more.

I use my iCloud (@me) for fun with family and friends and I use my outlook for anything sensitive. The reason I use outlook for sensitive is the 2 step verification, and I like that extra security with any email that is attached to anything that involves money.

 

[Bromio]

I think the best inter-device sync comes from picking ONE ecosystem and sticking with it. I'm all Apple, so iCloud works for me.

That's what I wanted to do, but owning Apple and Microsoft products simultaneously, it seems kind of impossible.

I have both and I'm stating to like outlook more and more.

I use my iCloud (@me) for fun with family and friends and I use my outlook for anything sensitive. The reason I use outlook for sensitive is the 2 step verification, and I like that extra security with any email that is attached to anything that involves money.

And are they well synchronized between all your devices?

 

[Primejimbo]

That's what I wanted to do, but owning Apple and Microsoft products simultaneously, it seems kind of impossible.



And are they well synchronized between all your devices?

I use iCloud for mail, contacts, and calendar. Outlook just for mail and no issues at all on my devices.

 

[iMacBooked]

I use iCloud for mail, contacts, and calendar. Outlook just for mail and no issues at all on my devices.

Same here.

 

[exi]

iCloud user here, former Gmail user, currently all Apple hardware. This is an issue I have revisited quite a bit. There are some small differences between the services that might matter to you. iCloud is a seamless as it gets for Apple hardware and is increasingly supported on the Windows side these days.

Outlook obviously utilizes ActiveSync which means that there are a few little limitations -- minor things like not fully supporting contact field labels, particularly for contact email addresss. The upcoming version of Office for Mac might bring us ActiveSync on the desktop if that matters to you and you're willing to use Outlook. Whereas iCloud doesn't update the unread count in the background on mobile devices, Outlook does as part of its version of ActiveSync.

And then there's the reliability question -- going by Internet anecdotes, it would seem that Outlook and Gmail may be more reliable in day to day usage than iCloud is as far as email sending/receiving. Everybody has their story about that one email that never reached its recipient, or about that one email that they swear they never received; while I'm sure this happens no matter what service you use, iCloud is gotten more flak for this in the past, not to mention their somewhat heavy-handed policy of silent email filtering for spam purposes, though other providers almost certainly do this as well.

 

[Primejimbo]

iCloud user here, former Gmail user, currently all Apple hardware. This is an issue I have revisited quite a bit. There are some small differences between the services that might matter to you. iCloud is a seamless as it gets for Apple hardware and is increasingly supported on the Windows side these days.

Outlook obviously utilizes ActiveSync which means that there are a few little limitations -- minor things like not fully supporting contact field labels, particularly for contact email addresss. The upcoming version of Office for Mac might bring us ActiveSync on the desktop if that matters to you and you're willing to use Outlook. Whereas iCloud doesn't update the unread count in the background on mobile devices, Outlook does as part of its version of ActiveSync.

And then there's the reliability question -- going by Internet anecdotes, it would seem that Outlook and Gmail may be more reliable in day to day usage than iCloud is as far as email sending/receiving. Everybody has their story about that one email that never reached its recipient, or about that one email that they swear they never received; while I'm sure this happens no matter what service you use, iCloud is gotten more flak for this in the past, not to mention their somewhat heavy-handed policy of silent email filtering for spam purposes, though other providers almost certainly do this as well.

You're right, they all have issues. I have to have 2 due to Apple not letting me use my @me for my iTunes log in, but more I think about it, it's not a big deal. I think having 2 separate email providers is a good idea too. One goes down, you have another one ready to go. As for that 1 email that we miss on I think we all have stories, personally it happens and I don't care. If someone sends me an email that is that important, they should follow up with a phone call.

More and more I use outlook (only with iOS) I do like the web version a lot. It's clean, simple, and no pre-made folders like gmail. I know all that can be turned off, but the cleaness out outlook.com is very nice I think. I never thought I see the day I like outlook/hotmail again too.

 

[whsbuss]

I use iCloud for mail, contacts, and calendar. Outlook just for mail and no issues at all on my devices.

We think alike. I also use OneDrive.

 

[Primejimbo]

We think alike. I also use OneDrive.

I forgot about that, we use it too.

 

[TechiEmmanuel]

From my experience, contacts, calendars, and reminders won't sync with OS X and Outlook mail.

 

[r0k]

I use iCloud for contacts, calendar and iTunes purchases. I also have email "pass through" iCloud to my final searchable email repository which is gmail.

I have 14+ years worth of email in gmail with everything over 18 months old "archived". It's still searchable from any web browser logged in to my gmail account but it doesn't get in the way of light email clients such as Apple Mail, Airmail, iPhone mail app, etc. I make a concerted effort to never send from my iCloud accounts because I prefer not to have my mac.com email address fall into the hands of my friends who might then start sending directly to that account and circumvent my carefully crafted email setup.

I find that iCloud is seamless for email but the storage costs have me keeping my main email repository on gmail. Now that iOS8 and OSX Yosemite were announced along with price cuts to iCloud storage, I will have to reexamine my setup.

I tend to use Apple for all things personal, Google for all things email and Amazon for all things books, music and movies. So far this strategy has worked well for me. I do have an Outlook account as well as a Yahoo account but I never touch them. I've allowed my flickr account to languish as well. Now that flickr is finally free, I should go back and reexamine that one as well.

 

[LoveMyPens]

I have gone back and forth and back and forth... a few times on this. Currently I am using iCloud for mail, calendar, contacts. I also a have Windows PC but the majority of my time is spent on my phone versus the PC. They are both great services but I keep coming back the iCloud, even though I have had a couple emails not send or not appear in sent items. I've tried splitting the services and it just doesn't work for me... I like having everything in one. With my wife and kids having iPhones/iPods, iCloud just makes more sense for me. I do use OneDrive as additional backup of pics/documents on my phone. Good luck if you haven't already decided.

 

[rctlr]

I have a number of email addresses which come into iCloud, and with rules against the email address, set up via the webpage, get moved into folders for review.

Contact, Calendar, notes and reminders are all managed by iCloud.

 

[Ray2]

I use both iCloud mail and Gmail, using Apple's mail apps on Mac's and iOS devices. I'm delighted with iCloud. The only issues I've ever had are, on occasion, mails do not get sent immediately and sit in the outbox for a while. Otherwise its much faster getting mail and Apple's apps support it well. Something that certainly cannot be said for Gmail.

Better spam blocking as well. It takes a while but it does learn.

 

[Bromio]

Thank you everybody.

Finally I've decided to use both iCloud and Outlook. Outlook is focused on my job issues, because its web interface is simpler and more accessible from old Windows computers.

For family and friends I have turned to iCloud, where I also use Notes, Reminders, Calendars...

 

[Primejimbo]

Thank you everybody.

Finally I've decided to use both iCloud and Outlook. Outlook is focused on my job issues, because its web interface is simpler and more accessible from old Windows computers.

For family and friends I have turned to iCloud, where I also use Notes, Reminders, Calendars...

The exact same route I went with this, and I am very happy with this set up too.

 

[terryblyth]

I've done something similar. I use Google Chrome (and Gmail within that) for work stuff, and iCloud for private stuff. I can keep everything separate then without having different logins.

 

[LoveMyPens]

I think the best inter-device sync comes from picking ONE ecosystem and sticking with it. I'm all Apple, so iCloud works for me.

So you have went back to iCloud? I do recall talking in various forums that you had issues with the mail reliability, messages disappearing or not delivering. Is this not the case anymore? I still revisit my options and have bounce back and forth from all 3 (iCloud, Outlook.com, & Gmail) over the last couple years.

 

[impaler]

So you have went back to iCloud? I do recall talking in various forums that you had issues with the mail reliability, messages disappearing or not delivering. Is this not the case anymore? I still revisit my options and have bounce back and forth from all 3 (iCloud, Outlook.com, & Gmail) over the last couple years.

Yes and no. I use both now. I just forward Gmail to iCloud. I still don't entirely trust iCloud, but like having it all in one place. Gmail is more of a pass through, so I have copies of emails...giving it a try for a few months to see if I miss anything.

 

[LoveMyPens]

Yes and no. I use both now. I just forward Gmail to iCloud. I still don't entirely trust iCloud, but like having it all in one place. Gmail is more of a pass through, so I have copies of emails...giving it a try for a few months to see if I miss anything.

I completely understand how you feel. Do reply from iCloud and just have the original email in Gmail? Just wondering the set you are using exactly. Sounds like our story/experiences are very similar.

 

[impaler]

I completely understand how you feel. Do reply from iCloud and just have the original email in gmail?

Yes.

 

[exi]

Just to chip in since I, like impaler, have had repeated issues of some sort or another with iCloud and have been vocal about them here on MR.

I'm doing partially the same. My main Gmail account forwards to my iCloud account and then deletes the originals, so I have the luxury to see if anything is lost in the redirect by checking Gmail's trash.

Many people do, however, use my iCloud address directly. I've tried Outlook.com. I still like Gmail. I'm too much a minimalist to not be annoyed at the idea of not having all my information consolidated in one service (contacts, calendaring, notes, etc, all with iCloud). I have not noticed any repeat issues with iCloud, either sending or receiving.

I'm getting to the point where I figure two things: one, life's too short to obsess over this nonsense, and any repeat issues will show themselves over time. And two, even for all the flack Apple has caught over the years for "not being good" at online services, surely they are working out issues pertaining to something as "simple" as mail sending and receiving. I realize that there's more to deliverability than meets the eye sometimes, but still.