Solved Weird iCloud Outlook problem - seems impossible to resolve


zaarin_2003

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Windows 11
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
 

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

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System One System Two

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    Windows 11 Home 24H2 26100.3915
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    Updated Windows 10 to 11 24H2 26100.3624
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Yahoo is already added to Zaarin’s Outlook account as he has stated. The issue is adding an iCoud calendar.


New Outlook in Windows 11

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
 

My Computers

System One System Two

  • OS
    Windows 11 Pro 23H2 Build 22631.5039
    Computer type
    PC/Desktop
    Manufacturer/Model
    Sin-built
    CPU
    Intel(R) Core(TM) i7-4770K CPU @ 3.50GHz (4th Gen?)
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    ASUS ROG Maximus VI Formula
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    32.0 GB of I forget and the box is in storage.
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    5 x LG 25MS500-B - 1 x 24MK430H-B - 1 x Wacom Pro 22" Tablet
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    All over the place
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    Too many to list.
    OS on Samsung 1TB 870 QVO SATA
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    NZXT Phantom 820 Full-Tower Case
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    Noctua NH-D15 Elite Class Dual Tower CPU Cooler / 6 x EziDIY 120mm / 2 x Corsair 140mm somethings / 1 x 140mm Thermaltake something / 2 x 200mm Corsair.
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    Windows 11 Pro 23H2 Build: 22631.4249
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    LENOVO Yoga 7i EVO OLED 14" Touchscreen i5 12 Core 16GB/512GB
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    Intel Core 12th Gen i5-1240P Processor (1.7 - 4.4GHz)
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    Optimized with Dolby Atmos®
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    M.2 512GB
    Antivirus
    Defender / Malwarebytes
    Other Info
    …still on a horse.

My Computers

System One System Two

  • OS
    Windows 11 Home 24H2 26100.3915
    Computer type
    PC/Desktop
    Manufacturer/Model
    HP Pavilion TP01-2xxx
    CPU
    AMD Ryzen 3 5300G
    Memory
    8gb
    Graphics Card(s)
    Radeon Graphics 4.00GHZ
    Monitor(s) Displays
    ViewSonic
    Keyboard
    HP
    Mouse
    wireless Microsoft
    Browser
    FireFox
    Antivirus
    Avira
  • Operating System
    Updated Windows 10 to 11 24H2 26100.3624
    Computer type
    PC/Desktop
    Manufacturer/Model
    HP
    CPU
    Intel Core i3 8100 @3.60 GHz
    Motherboard
    HP 8653 (U3E1)
    Memory
    8.GB
    Graphics card(s)
    Intel UHD 360 (HP)
    Sound Card
    Realtek High Def
    Monitor(s) Displays
    ViewSonic
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.
 

My Computers

System One System Two

  • OS
    Windows 11 Pro 23H2 Build 22631.5039
    Computer type
    PC/Desktop
    Manufacturer/Model
    Sin-built
    CPU
    Intel(R) Core(TM) i7-4770K CPU @ 3.50GHz (4th Gen?)
    Motherboard
    ASUS ROG Maximus VI Formula
    Memory
    32.0 GB of I forget and the box is in storage.
    Graphics Card(s)
    Gigabyte nVidia GeForce GTX 1660 Super OC 6GB
    Sound Card
    Onboard
    Monitor(s) Displays
    5 x LG 25MS500-B - 1 x 24MK430H-B - 1 x Wacom Pro 22" Tablet
    Screen Resolution
    All over the place
    Hard Drives
    Too many to list.
    OS on Samsung 1TB 870 QVO SATA
    PSU
    Silverstone 1500
    Case
    NZXT Phantom 820 Full-Tower Case
    Cooling
    Noctua NH-D15 Elite Class Dual Tower CPU Cooler / 6 x EziDIY 120mm / 2 x Corsair 140mm somethings / 1 x 140mm Thermaltake something / 2 x 200mm Corsair.
    Keyboard
    Corsair K95 / Logitech diNovo Edge Wireless
    Mouse
    Logitech: G402 / G502 / Mx Masters / MX Air Cordless
    Internet Speed
    1000/400Mbps
    Browser
    All sorts
    Antivirus
    Kaspersky Premium
    Other Info
    I’m on a horse.
  • Operating System
    Windows 11 Pro 23H2 Build: 22631.4249
    Computer type
    Laptop
    Manufacturer/Model
    LENOVO Yoga 7i EVO OLED 14" Touchscreen i5 12 Core 16GB/512GB
    CPU
    Intel Core 12th Gen i5-1240P Processor (1.7 - 4.4GHz)
    Memory
    16GB LPDDR5 RAM
    Graphics card(s)
    Intel Iris Xe Graphics Processor
    Sound Card
    Optimized with Dolby Atmos®
    Screen Resolution
    QHD 2880 x 1800 OLED
    Hard Drives
    M.2 512GB
    Antivirus
    Defender / Malwarebytes
    Other Info
    …still on a horse.
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.
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).
 

My Computer

System One

  • OS
    Windows 11
    Computer type
    PC/Desktop
    CPU
    i9 9900
    Motherboard
    Z390 Gigabyte Aorus Elite
    Memory
    32 Gb DDR4
    Graphics Card(s)
    nVidia 1070
    Sound Card
    Realtek
    Monitor(s) Displays
    Samsung 4k
    Screen Resolution
    4k
    Hard Drives
    Intel Optane 905p
    PSU
    600w
    Browser
    Edge
    Antivirus
    Microsoft Defender
I don't know exactly what Outlook this is

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.
 

My Computers

System One System Two

  • OS
    Windows 11 Pro 23H2 Build 22631.5039
    Computer type
    PC/Desktop
    Manufacturer/Model
    Sin-built
    CPU
    Intel(R) Core(TM) i7-4770K CPU @ 3.50GHz (4th Gen?)
    Motherboard
    ASUS ROG Maximus VI Formula
    Memory
    32.0 GB of I forget and the box is in storage.
    Graphics Card(s)
    Gigabyte nVidia GeForce GTX 1660 Super OC 6GB
    Sound Card
    Onboard
    Monitor(s) Displays
    5 x LG 25MS500-B - 1 x 24MK430H-B - 1 x Wacom Pro 22" Tablet
    Screen Resolution
    All over the place
    Hard Drives
    Too many to list.
    OS on Samsung 1TB 870 QVO SATA
    PSU
    Silverstone 1500
    Case
    NZXT Phantom 820 Full-Tower Case
    Cooling
    Noctua NH-D15 Elite Class Dual Tower CPU Cooler / 6 x EziDIY 120mm / 2 x Corsair 140mm somethings / 1 x 140mm Thermaltake something / 2 x 200mm Corsair.
    Keyboard
    Corsair K95 / Logitech diNovo Edge Wireless
    Mouse
    Logitech: G402 / G502 / Mx Masters / MX Air Cordless
    Internet Speed
    1000/400Mbps
    Browser
    All sorts
    Antivirus
    Kaspersky Premium
    Other Info
    I’m on a horse.
  • Operating System
    Windows 11 Pro 23H2 Build: 22631.4249
    Computer type
    Laptop
    Manufacturer/Model
    LENOVO Yoga 7i EVO OLED 14" Touchscreen i5 12 Core 16GB/512GB
    CPU
    Intel Core 12th Gen i5-1240P Processor (1.7 - 4.4GHz)
    Memory
    16GB LPDDR5 RAM
    Graphics card(s)
    Intel Iris Xe Graphics Processor
    Sound Card
    Optimized with Dolby Atmos®
    Screen Resolution
    QHD 2880 x 1800 OLED
    Hard Drives
    M.2 512GB
    Antivirus
    Defender / Malwarebytes
    Other Info
    …still on a horse.
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?
 

My Computers

System One System Two

  • OS
    Windows 11 Pro 23H2 Build 22631.5039
    Computer type
    PC/Desktop
    Manufacturer/Model
    Sin-built
    CPU
    Intel(R) Core(TM) i7-4770K CPU @ 3.50GHz (4th Gen?)
    Motherboard
    ASUS ROG Maximus VI Formula
    Memory
    32.0 GB of I forget and the box is in storage.
    Graphics Card(s)
    Gigabyte nVidia GeForce GTX 1660 Super OC 6GB
    Sound Card
    Onboard
    Monitor(s) Displays
    5 x LG 25MS500-B - 1 x 24MK430H-B - 1 x Wacom Pro 22" Tablet
    Screen Resolution
    All over the place
    Hard Drives
    Too many to list.
    OS on Samsung 1TB 870 QVO SATA
    PSU
    Silverstone 1500
    Case
    NZXT Phantom 820 Full-Tower Case
    Cooling
    Noctua NH-D15 Elite Class Dual Tower CPU Cooler / 6 x EziDIY 120mm / 2 x Corsair 140mm somethings / 1 x 140mm Thermaltake something / 2 x 200mm Corsair.
    Keyboard
    Corsair K95 / Logitech diNovo Edge Wireless
    Mouse
    Logitech: G402 / G502 / Mx Masters / MX Air Cordless
    Internet Speed
    1000/400Mbps
    Browser
    All sorts
    Antivirus
    Kaspersky Premium
    Other Info
    I’m on a horse.
  • Operating System
    Windows 11 Pro 23H2 Build: 22631.4249
    Computer type
    Laptop
    Manufacturer/Model
    LENOVO Yoga 7i EVO OLED 14" Touchscreen i5 12 Core 16GB/512GB
    CPU
    Intel Core 12th Gen i5-1240P Processor (1.7 - 4.4GHz)
    Memory
    16GB LPDDR5 RAM
    Graphics card(s)
    Intel Iris Xe Graphics Processor
    Sound Card
    Optimized with Dolby Atmos®
    Screen Resolution
    QHD 2880 x 1800 OLED
    Hard Drives
    M.2 512GB
    Antivirus
    Defender / Malwarebytes
    Other Info
    …still on a horse.
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.
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!
 

My Computer

System One

  • OS
    Windows 11
    Computer type
    PC/Desktop
    CPU
    i9 9900
    Motherboard
    Z390 Gigabyte Aorus Elite
    Memory
    32 Gb DDR4
    Graphics Card(s)
    nVidia 1070
    Sound Card
    Realtek
    Monitor(s) Displays
    Samsung 4k
    Screen Resolution
    4k
    Hard Drives
    Intel Optane 905p
    PSU
    600w
    Browser
    Edge
    Antivirus
    Microsoft Defender

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