Solved Weird iCloud Outlook problem - seems impossible to resolve

Hi,

My primary email account is a Yahoo (because I'm old) email. New Outlook in Windows 11 allowed me to add this account no problem, and so I see all my favourite spam in my email when I open Outlook, just as you would want.

However, my primary calendar app is on my iPhone, which is obviously tied to my iCloud account. I would therefore like to add this iCloud account to Outlook. I just can't seem to be able to do this? Why not? Well, I'm aware of generating app-specific passwords and have tried adding the account using Apple's IMAP settings and all that jazz, but that's not the problem. The problem is that when I signed up for iCloud, oh, back in 2010 or so, it allowed me to use my Yahoo email address. Basically, my iCloud log in/username/email address is the same email address as my Yahoo email.

So, what happens is, if I try to add my icloud address to Outlook, it understandably tries to log me into Yahoo to grant access, and eventually says, 'you've already added this account'. Well, no I haven't, but I get it. If I try to add the account manually using the IMAP settings, it doesn't like it and says there's some error, even though there isn't one.

The annoying thing is, that old Outlook and the Windows 10 mail app, had no problem. I just said 'add iCloud account' or 'add Yahoo account' and added in my username (the same for both) and password and they both were added no problem at all.

Any ideas?

Thanks!

M

See the last reply in this topic about adding yahoo email to Outlook: Redirecting

Yahoo is already added to Zaarin’s Outlook account as he has stated. The issue is adding an iCoud calendar.

zaarin_2003 said:

New Outlook in Windows 11

Click to expand...

Zaarin, I have to ask (because Microsoft )

When you say New Outlook (or Outlook (New)) are you referring to Windows native “APP” or new Outlook related to Microsoft 365

Possibly? Add or manage an iCloud email account in Outlook - Microsoft Support
Or this with 'classic' ICloud: Add or manage an iCloud email account in Outlook - Microsoft Support

Jacee said:

Possibly? Add or manage an iCloud email account in Outlook - Microsoft Support
Or this with 'classic' ICloud: Add or manage an iCloud email account in Outlook - Microsoft Support

Click to expand...

Good find.
Now to be able to explain to outlook that:

• The main email address is Yahoo
• The email address linked to the iCloud Calendar is the same email address but, for a different process.
  • Outlook is not discriminating between Yahoo and iCloud even though they are different services, because they are both using the same yahoo address.

@zaarin_2003, is Outlook calling on the iCloud server or the Yahoo server by mistake, can you see in the settings? (Not that I’ve been able to find any calendar specific settings
I did find iCloud IMAP settings

Also:

You can use iCloud for Windows to synchronize your calendar and contacts between your iOS device and Outlook. To install iCloud for Windows, use the following steps.

1. Download and install iCloud for Windows.
2. After installation, launch the iCloud app and sign in with your Apple ID and password.
3. In the iCloud app, select the option to sync Contacts and Calendars, then click Apply.
4. Once the setup has finished, launch Outlook. Your iCloud contacts and calendars should now be synchronizing with Outlook.

antspants said:

Good find.
Now to be able to explain to outlook that:

• The main email address is Yahoo
• The email address linked to the iCloud Calendar is the same email address but, for a different process.
  • Outlook is not discriminating between Yahoo and iCloud even though they are different services, because they are both using the same yahoo address.

@zaarin_2003, is Outlook calling on the iCloud server or the Yahoo server by mistake, can you see in the settings? (Not that I’ve been able to find any calendar specific settings
I did find iCloud IMAP settings

Also:

You can use iCloud for Windows to synchronize your calendar and contacts between your iOS device and Outlook. To install iCloud for Windows, use the following steps.

1. Download and install iCloud for Windows.
2. After installation, launch the iCloud app and sign in with your Apple ID and password.
3. In the iCloud app, select the option to sync Contacts and Calendars, then click Apply.
4. Once the setup has finished, launch Outlook. Your iCloud contacts and calendars should now be synchronizing with Outlook.

Set up iCloud for Windows on your PC

Learn how to sign in to iCloud for Windows and turn features on and off.

support.apple.com

Click to expand...

Hi both,

Yes, I have Googled and tried these methods already. It doesn't help! I followed Add or manage an iCloud email account in Outlook - Microsoft Support and the moment I put in my email address, with it added as Yahoo already, Outlook tries to be clever and tries to add it as a Yahoo account, there's no option to tell it I actually want to address as an iCloud account as well. It does this even if the email is not yet added at all.

Before it gets to the point where it incorrectly guesses I'm trying to add a Yahoo account twice, I can tick advanced and it lets me override the automatic thing it tries to do detailed above, and so I can effectively say 'no, let me add the account manually'. At that point, I am allowed to enter my email address and then enter the iCloud IMAP details. I use the ones you have linked to, but just get a log in error. I use the IMAP details exactly and have tried both my iCloud password and an app specific password. No dice.

I don't know exactly what Outlook this is - I think it's the one built into Windows 11 because that one says 'open' on the app store. It is listed under Installed apps as Outlook (new). Outlook (classic) is also on the start menu and that works exactly as I want it to, but you can only use one or the other, not both, and you have to switch between them. If I use classic, then every now and then MS switches it to (new) without asking me and keeps telling me the classic version is being phased out, so it's not really a solution.

I do have Office 365 and when I launch Outlook from within the 365 launcher, it launches the same version (new).

zaarin_2003 said:

I don't know exactly what Outlook this is

Click to expand...

Outlook in the Microsoft 365 suite, as far as I could see after connecting remotely to a member here, is called Outlook Classic.

But that could be depending on more factors than I have hair to pull out.
The person who I connected to still had a "New Outlook" toggle on the top right of their 365 version

What I eventually did was figure which was the App and which was from the 365 Suite, and removed the App version


What a pain in the rear.

If it turns out you're not taking advantage of your 365 subscription version "Outlook Classic" Hunt it down and try it.

You could

Open search (Win + S) search for Outlook.
You will more than likely see more than one version.

Open both (one at a time) Identified by the icon? (one would hope)
I suspect one will have your email and one may not?

antspants said:

Outlook in the Microsoft 365 suite, as far as I could see after connecting remotely to a member here, is called Outlook Classic.

But that could be depending on more factors than I have hair to pull out.
The person who I connected to still had a "New Outlook" toggle on the top right of their 365 version

What I eventually did was figure which was the App and which was from the 365 Suite, and removed the App version

What version of Outlook do I have? | Microsoft Support

Learn what version of Outlook you're using, and get link for setup, how to import and export email, contacts, and calendar.

support.microsoft.com

What a pain in the rear.

If it turns out you're not taking advantage of your 365 subscription version "Outlook Classic" Hunt it down and try it.

Click to expand...

Ok, I fixed it! It was quite simple in the end.

Apple/iCloud allows two email addresses (or more, I'm not sure) to be tied to the same iCloud account. So I added an @icloud.com one. Outlook of course allowed me to add that, and because it is tied to the same iCloud account, it carried all my calendar entries to Outlook with it. Presto!