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iCloud for Windows Outlook Integration - Does it suck or is it just me?

Yebubbleman

macrumors 68040
Original poster
May 20, 2010
3,739
840
Los Angeles, CA
I own and operate a ton of computers. These days, most of them are Windows 10 PCs. My primary e-mail account is the one provided to me by iCloud for free. On most of the Windows 10 PCs that I use, I either use the stock Windows 10 Mail app or Outlook 2016 and I just generate an app-specific password (yay for two-factor authentication!) when setting up the account. However, on the Dell Latitude 7390 listed in my signature (which I primarily use for maintaining my iTunes library and interfacing with iCloud; I tend to keep my iCloud off of my other PCs), I use my Microsoft (Office) 365 Home subscription and have the subscription's version of Outlook installed on it with iCloud for Windows also installed.

On the PCs that I manually log into either the stock Windows 10 Mail app or Outlook 2016 with the app-specific password, everything works wonderfully! On the Latitude 7390 with iCloud for Windows set up to sync with 365-subscription Outlook (I think I'm running version 2008?), mail does not come in promptly unless I close Outlook completely and re-open it. It won't sync all the time nor will it do so consistently when I do sync it.

I do love that my contacts and calendars get synced with Outlook that way, but it's otherwise way worse than if I had just done it without the help of iCloud for Windows' help to begin with.

Is this normal behavior? Should I just avoid using iCloud for Windows to keep Outlook on my Latitude 7390 in sync? Am I having issues because I'm using the 365 Outlook rather than 2016 or 2019? Does iCloud for Windows' Outlook integration just suck? Or did I do something wrong in setting things up?

Any insight on this would be most helpful! Thanks in advance!
 

Namara

Contributor
Apr 16, 2020
2,978
2,841
East of the sun, west of the moon
Not sure what to suggest to help. I use iCloud for Windows on my PC with MS365 (Home version) Outlook (version 1908) and not having the issues you're describing. I have both my Outlook.com and iCloud email accounts configured for it. I also have both configured in Outlook for iPadOS and iOS and no issues there either. I'm pretty pleased with iCloud for Windows (and iTunes for Windows too, which I only use for iPad/iPhone backups).
 

Namara

Contributor
Apr 16, 2020
2,978
2,841
East of the sun, west of the moon
By the way there's an updated version of iCloud for Windows released this week. It doesn't look like it addresses Outlook issues explicitly, but seems like a good idea to be on the latest version:

 

Yebubbleman

macrumors 68040
Original poster
May 20, 2010
3,739
840
Los Angeles, CA
Not sure what to suggest to help. I use iCloud for Windows on my PC with MS365 (Home version) Outlook (version 1908) and not having the issues you're describing. I have both my Outlook.com and iCloud email accounts configured for it. I also have both configured in Outlook for iPadOS and iOS and no issues there either. I'm pretty pleased with iCloud for Windows (and iTunes for Windows too, which I only use for iPad/iPhone backups).

Your Outlook version is a bit beyond mine (I'm on 2008). I'm also on Windows 10 v2004 on said Latitude 7390, if that helps.

I'm also not keen on iCloud for Windows forcibly creating a PST archive file (for what purpose?).
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I'll definitely update iCloud for Windows to see if that helps! Thanks for the heads up!
 
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