Best configuration for Outlook 2016, Gmail and iCloud

Outlook version
Outlook 2016 64 bit
Email Account
IMAP
#1
I couldn't get my Windows 7, Outlook 2013 and iCloud worlds to align, so I decided to start from scratch - upgraded my PC to Windows 10 Home and subscribed to Office 365. I'm looking for someone to suggest the best configuration to get these three to play together nicely.

My default Email account is Gmail. I may, from time-to-time map an additional Email account to Outlook, but I want my base account to work right. I use an iPhone for calendar and contacts, and they're backed up in iCloud.

I want to use the Outlook client when I'm sitting in front of my PC. My Inbox and folders should come from my Gmail account. Calendar invitations that I get in Gmail should post to the calendar. The calendar and contacts in Outlook should sync to my iPhone so that any calendar entry or contact addition, either on the iPhone or via Outlook, gets backed up to iCloud.

I had all this working at one point on my work PC using Outlook 2016, Windows 10 Pro and iCloud for Windows, but I had the help of my IT support person. I'm working independently now from home, and need to support myself!

I'm not afraid to edit registry entries, etc., and I've surfed this site and got some good ideas. But I didn't want to start until I got some suggestions.

Thanks, in advance, for your help.
 
Outlook version
Outlook 2016 32 bit
Email Account
Office 365 Exchange
#2
Are you getting any error messages? It should have worked with Window 7/Outlook 2013.

You shouldn't have to edit the registry - just install office, set up the email account, install icloud, sign in and enable calendar & contact sync.
 
Outlook version
Outlook 2016 64 bit
Email Account
IMAP
#3
Diane,

Thanks for all your help. After installing O365, I launched Outlook for the first time and the mailbox looked like it did before. One Inbox, and a [Gmail] folder with all my nested Gmail labels appearing as folders.

After I installed iCloud for Windows is when things got confusing. I only checked the Calendar, Contacts and Tasks box to sync, and it took a while for all the contacts and calendar entries to sync. When it finished, there was a "My Calendars" section with "Calendar (this Computer Only)", and and iCloud section with four calendars - George's Calendar (the one on my iPhone), Home (Shared) - my wife's calendar, one just called Calendar, and one that looked like it was deleted from my Gmail account.

I unchecked the Calendar (this computer only), and deleted the Calendar and deleted Gmail calendar from the iCloud section. The calendar view appears to be normal.

The final issue relates to Tasks & ToDos. Under "My Tasks", there are two folders - To-Do List and Tasks (This computer only). Under iCloud, there were two - Tasks and the group of tasks that looked like they were deleted from my Gmail calendar. I moved these tasks to the iCloud folder, and then deleted it.

I don't understand how the remaining three folders - My Tasks/To-Do List, My Tasks/Tasks (This computer Only, and iCloud/Tasks - interact with one another. When I create a task from Outlook Email, the task appears in Tasks (This computer only) which probably means it won't sync with iCloud.

Thanks, in advance, for your help.

George
 
Outlook version
Outlook 2016 32 bit
Email Account
Office 365 Exchange
#4
icloud usually deletes the 'this computer only' folders - as in moves them to trash so you don't see them on the navigation panes. The 'this computer only' folders are created when you set an IMAP data file as the default (new feature as of Outlook 2013) I don't like them - too much risk of data loss - but when you use icloud, its not so bad because icloud sucks everything into it's own folders.

You shouldn't use the 'this computer only folders' , but outlook will use them for accepted meetings and if you click on a sender's name and add to contacts.

The final issue relates to Tasks & ToDos. Under "My Tasks", there are two folders - To-Do List and Tasks (This computer only). Under iCloud, there were two - Tasks and the group of tasks that looked like they were deleted from my Gmail calendar. I moved these tasks to the iCloud folder, and then deleted it.
To-Dos are all flagged messages and tasks under in the profile. This one: Tasks (This computer only) is in the gmail data file.
 
Outlook version
Outlook 2016 64 bit
Email Account
IMAP
#5
Sorry to be dense here, but I'm still not following.

My Outlook is mapped to my Gmail account. I have the iCloud Add-in installed but it's not working as desired.

I'd like Outlook ToDos to sync to iCloud Reminders (so I can see them on my iPhone) and I'd like calendar entries on my iPhone (i.e. my iCloud calendar) to be the default calendar for Outlook so when I "Create Task", "Create Meeting", or accept a meeting invitation from my InBox.

I had all this working when I was in a corporate setting with Outlook/Exchange - I've been unable to get it working on my standalone PC with Outlook from O365.

Thank you, in advance for your assistance.
 
Outlook version
Outlook 2016 32 bit
Email Account
Office 365 Exchange
#6
I'd like Outlook ToDos to sync to iCloud Reminders
Tasks will sync, but not flagged messages that are on the to-do list.

I'd like calendar entries on my iPhone (i.e. my iCloud calendar) to be the default calendar for Outlook
The icloud data file cant be set as default (well, it can be, with some builds of outlook and iCloud, but its pretty buggy).
 

Len Raphael

Senior Member
Outlook version
Outlook 2016 64 bit
Email Account
Office 365 Exchange
#7
is the conclusion still that there's nothing gained by Office 365 users with iphones, by installing Icloud on their Windows PC's?

Since Outlook calendar still doesn't allow more than one notification per calendar event, but the Iphone calendar allows two, I erroneously thought installing Icloud locally would give me local access to the Icloud calendar. But that's not what it does. And it does some wierd stuff with invites made from the Apple Iphone calendar app. So I'll uninstall from PC.

So it seems the workaround to get two notifications at least on the Iphone is to make the appt thru Outlook on the PC. Then open Apple Calendar on Iphone and add second notification. Am I missing something?
 

Diane Poremsky

Senior Member
Outlook version
Outlook 2016 32 bit
Email Account
Office 365 Exchange
#8
if 'office 365 user' means office 365 or outlook.com mailboxes, there is no benefit to using icloud but lots of negatives.

locally would give me local access to the Icloud calendar.
If there are events in the icloud cakebdar, definitely should sync down..

So it seems the workaround to get two notifications at least on the Iphone is to make the appt thru Outlook on the PC. Then open Apple Calendar on Iphone and add second notification. Am I missing something?
AFAIK no you are not missing anything.
 

Len Raphael

Senior Member
Outlook version
Outlook 2016 64 bit
Email Account
Office 365 Exchange
#9
but turns out that in July 2018, Apple removed ability to add second notification to a calendar event. At least on iphone.

Trying an iphone add on app CalAlarm that has a "nag" function. But a reminder to remind me to configure the nag after creating the event o my pc or iphone calendar. But it does seem to work.
 

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