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!
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!