iCloud for Windows setup fails

Environment:
Windows 10 for home 64-bit
Dell Studio XPS 8000
12gb memory
Outlook 2019

Load iCloud for Windows
Turn on sync for Calendars & Contacts
Error message: “Your setup couldn’t start because your username or
password is incorrect. Go to iCloud for Windows, sign out, sign back in”
Log out of iCloud
Log in to iCloud
Turn on sync for Calendars & Contacts
Same error message "Your setup couldn’t start because your username or
password is incorrect. Go to iCloud for Windows, sign out, sign back in”

Things I have tried:
1) Checked that the iCloud for Outlook Add-in is active
2) Reinstalled Office 2019
3) Uninstalled & installed iCloud for Windows

I also have a Dell laptop running Windows 10 Home 64-bit with Outlook
2019 and iCloud syncing Calendars & Contacts works.

Anybody got any hints on how to get setup to work?

Jim

On 2/26/2024 9:38 AM, Jim Dell wrote:
> iCloud for Windows setup fails
>
> Environment:
> Windows 10 for home 64-bit
> Dell Studio XPS 8000
>     12gb memory
> Outlook 2019
>
> Load iCloud for Windows
> Turn on sync for Calendars & Contacts
> Error message: “Your setup couldn’t start because your username or password is incorrect. Go to iCloud for Windows, sign out, sign back in”
> Log out of iCloud
> Log in to iCloud
> Turn on sync for Calendars & Contacts
> Same error message "Your setup couldn’t start because your username or password is incorrect. Go to iCloud for Windows, sign out, sign back in”
>
> Things I have tried:
> 1)    Checked that the iCloud for Outlook Add-in is active
> 2)    Reinstalled Office 2019
> 3)    Uninstalled & installed iCloud for Windows
>
> I also have a Dell laptop running Windows 10 Home 64-bit with Outlook 2019 and iCloud syncing Calendars & Contacts works.
>
> Anybody got any hints on how to get setup to work?
>
> Jim
>

Maybe you could pair with your iPhone over Bluetooth, then
try logging into iCloud on Windows ? Give it a "whiff of ecosystem"
as encouragement. Chanel 1984.

Normally I would say something silly like "check yer firewall"
but I bet the network light is flickering when you try to
authenticate. If you don't have lights available, you can
Wireshark and capture a trace, and at least see what
domains it is accessing.

And this would not be the first time they botched cross-platform
auth. This shit used to drive me nuts, not being able to use
File Sharing on my Mac, because "Nobody Cared Enough To Fix it".

None of the tutorial articles mention a thing about authorizing
the App to do things like access your camera or microphone. Normally
an App has permission settings. As well as potentially Firewall issues.
But none of the tutorials mention this, so I assume they've just
paved these flat somehow. If a small developer wrote the App, then
the instructions would give a lengthy list of perms to set (slide
switches).

There's no technical reason it should be having trouble opening
a TLS connection to apple.com while passing your username/password.
That's why I came up with the Bluetooth suggestion, in case they've
got some sort of "Advances Security" as default, in mind. There's no
particular reason the "old" reviews I looked at, would mention this.

If you put apple.com 127.0.0.1 in the HOSTS file, that wouldn't
be too clever. Or if you have a PiHole in your setup doing stuff.

Paul

Jim Dell <Jim.Dell@gmail.com> wrote:

> iCloud for Windows setup fails
>
> Environment:
> Windows 10 for home 64-bit
> Dell Studio XPS 8000
> 12gb memory
> Outlook 2019
>
> Load iCloud for Windows
> Turn on sync for Calendars & Contacts
> Error message: “Your setup couldn’t start because your username or
> password is incorrect. Go to iCloud for Windows, sign out, sign back in”
> Log out of iCloud
> Log in to iCloud
> Turn on sync for Calendars & Contacts
> Same error message "Your setup couldn’t start because your username or
> password is incorrect. Go to iCloud for Windows, sign out, sign back in”
>
> Things I have tried:
> 1) Checked that the iCloud for Outlook Add-in is active
> 2) Reinstalled Office 2019
> 3) Uninstalled & installed iCloud for Windows
>
> I also have a Dell laptop running Windows 10 Home 64-bit with Outlook
> 2019 and iCloud syncing Calendars & Contacts works.

Did you create an Apple ID account to which the iCloud client can
connect? iCloud is an Apple thing, and you need an Apple account to use
it.

Are you using the same login credentials in the iCloud client as you use
when logging into Apple's iCloud web site (icloud.com)? After logging
into their iCloud web site, make sure data web access is enabled. When
I got rid of my only Apple device, I kept the iCloud account, but
disabled data web access, so clients can no longer use it to access data
in Apple's cloud.

Note that add-ins for Outlook are written using VBA, and your issue is
not with Windows 10. The Outlook newsgroup would be a proper place to
ask. There are also the web forums for iCloud communities to ask for
help (https://discussions.apple.com/community/icloud). No idea how they
treat Windows users asking for help on Outlook add-ins.

I found https://apps.microsoft.com/detail/9pktq5699m62?hl=en-US&gl=US.
That's a client to access iCloud data. It is not an Outlook add-in.
Does that install an add-in into Outlook? Maybe it does since
https://support.apple.com/en-us/102436 mentions both the iCloud client
and Outlook.

https://support.apple.com/en-us/HT204230
System requirements for iCloud
....
PC
Microsoft Windows 11 or later*
iCloud for Windows 15
Outlook 2019 or later
Firefox 92 or later, Google Chrome 100 or later (desktop mode only),
or Microsoft Edge 100 or later
* 64-bit Windows (May 2019 Update or later) is required to install
iCloud for Windows.

Doesn't mention Windows 10 is supported. You might've gotten it working
on your other Windows 10 host, but Apple doesn't support it there.
However, the MS Store says the app runs on Windows 10. Conflicting info
from MS and Apple.

Jim Dell wrote on 2/26/24 7:38 AM:
> iCloud for Windows setup fails
>
> Environment:
> Windows 10 for home 64-bit
> Dell Studio XPS 8000
>     12gb memory
> Outlook 2019
>
> Load iCloud for Windows
> Turn on sync for Calendars & Contacts
> Error message: “Your setup couldn’t start because your username or
> password is incorrect. Go to iCloud for Windows, sign out, sign back in”
> Log out of iCloud
> Log in to iCloud
> Turn on sync for Calendars & Contacts
> Same error message "Your setup couldn’t start because your username or
> password is incorrect. Go to iCloud for Windows, sign out, sign back in”
>
> Things I have tried:
> 1)    Checked that the iCloud for Outlook Add-in is active
> 2)    Reinstalled Office 2019
> 3)    Uninstalled & installed iCloud for Windows
>
> I also have a Dell laptop running Windows 10 Home 64-bit with Outlook
> 2019 and iCloud syncing Calendars & Contacts works.
>
> Anybody got any hints on how to get setup to work?
>
> Jim
>

Did you create a primary icloud email address in your icloud account?
Did you setup the primary icloud email address in Outlook?
Did you setup the primary icloud email address with an app specific
password and use that password for the primary icloud password(when
setting up the icloud email in Outlook)?

--
....w¡ñ§±¤ñ

VanguardLH wrote:
> Jim Dell <Jim.Dell@gmail.com> wrote:
>
>> iCloud for Windows setup fails
>>
>> Environment:
>> Windows 10 for home 64-bit
>> Dell Studio XPS 8000
>> 12gb memory
>> Outlook 2019
>>
>> Load iCloud for Windows
>> Turn on sync for Calendars & Contacts
>> Error message: “Your setup couldn’t start because your username or
>> password is incorrect. Go to iCloud for Windows, sign out, sign back in”
>> Log out of iCloud
>> Log in to iCloud
>> Turn on sync for Calendars & Contacts
>> Same error message "Your setup couldn’t start because your username or
>> password is incorrect. Go to iCloud for Windows, sign out, sign back in”
>>
>> Things I have tried:
>> 1) Checked that the iCloud for Outlook Add-in is active
>> 2) Reinstalled Office 2019
>> 3) Uninstalled & installed iCloud for Windows
>>
>> I also have a Dell laptop running Windows 10 Home 64-bit with Outlook
>> 2019 and iCloud syncing Calendars & Contacts works.
>
> Did you create an Apple ID account to which the iCloud client can
> connect? iCloud is an Apple thing, and you need an Apple account to use
> it.
>
> Are you using the same login credentials in the iCloud client as you use
> when logging into Apple's iCloud web site (icloud.com)? After logging
> into their iCloud web site, make sure data web access is enabled. When
> I got rid of my only Apple device, I kept the iCloud account, but
> disabled data web access, so clients can no longer use it to access data
> in Apple's cloud.
>
> Note that add-ins for Outlook are written using VBA, and your issue is
> not with Windows 10. The Outlook newsgroup would be a proper place to
> ask. There are also the web forums for iCloud communities to ask for
> help (https://discussions.apple.com/community/icloud). No idea how they
> treat Windows users asking for help on Outlook add-ins.
>
> I found https://apps.microsoft.com/detail/9pktq5699m62?hl=en-US&gl=US.
> That's a client to access iCloud data. It is not an Outlook add-in.
> Does that install an add-in into Outlook? Maybe it does since
> https://support.apple.com/en-us/102436 mentions both the iCloud client
> and Outlook.
>
> https://support.apple.com/en-us/HT204230
> System requirements for iCloud
> ...
> PC
> Microsoft Windows 11 or later*
> iCloud for Windows 15
> Outlook 2019 or later
> Firefox 92 or later, Google Chrome 100 or later (desktop mode only),
> or Microsoft Edge 100 or later
> * 64-bit Windows (May 2019 Update or later) is required to install
> iCloud for Windows.
>
> Doesn't mention Windows 10 is supported. You might've gotten it working
> on your other Windows 10 host, but Apple doesn't support it there.
> However, the MS Store says the app runs on Windows 10. Conflicting info
> from MS and Apple.
>
Yes I have a iCloud account. Works on iTunes, works on iCloud sync
Photos & iCloud.com
..
I do not own a iPhone, I own a iPad.

Jim

Paul wrote:
> On 2/26/2024 9:38 AM, Jim Dell wrote:
>> iCloud for Windows setup fails
>>
>> Environment:
>> Windows 10 for home 64-bit
>> Dell Studio XPS 8000
>>     12gb memory
>> Outlook 2019
>>
>> Load iCloud for Windows
>> Turn on sync for Calendars & Contacts
>> Error message: “Your setup couldn’t start because your username or password is incorrect. Go to iCloud for Windows, sign out, sign back in”
>> Log out of iCloud
>> Log in to iCloud
>> Turn on sync for Calendars & Contacts
>> Same error message "Your setup couldn’t start because your username or password is incorrect. Go to iCloud for Windows, sign out, sign back in”
>>
>> Things I have tried:
>> 1)    Checked that the iCloud for Outlook Add-in is active
>> 2)    Reinstalled Office 2019
>> 3)    Uninstalled & installed iCloud for Windows
>>
>> I also have a Dell laptop running Windows 10 Home 64-bit with Outlook 2019 and iCloud syncing Calendars & Contacts works.
>>
>> Anybody got any hints on how to get setup to work?
>>
>> Jim
>>
>
> Maybe you could pair with your iPhone over Bluetooth, then
> try logging into iCloud on Windows ? Give it a "whiff of ecosystem"
> as encouragement. Chanel 1984.
>
> Normally I would say something silly like "check yer firewall"
> but I bet the network light is flickering when you try to
> authenticate. If you don't have lights available, you can
> Wireshark and capture a trace, and at least see what
> domains it is accessing.
>
> And this would not be the first time they botched cross-platform
> auth. This shit used to drive me nuts, not being able to use
> File Sharing on my Mac, because "Nobody Cared Enough To Fix it".
>
> None of the tutorial articles mention a thing about authorizing
> the App to do things like access your camera or microphone. Normally
> an App has permission settings. As well as potentially Firewall issues.
> But none of the tutorials mention this, so I assume they've just
> paved these flat somehow. If a small developer wrote the App, then
> the instructions would give a lengthy list of perms to set (slide
> switches).
>
> There's no technical reason it should be having trouble opening
> a TLS connection to apple.com while passing your username/password.
> That's why I came up with the Bluetooth suggestion, in case they've
> got some sort of "Advances Security" as default, in mind. There's no
> particular reason the "old" reviews I looked at, would mention this.
>
> If you put apple.com 127.0.0.1 in the HOSTS file, that wouldn't
> be too clever. Or if you have a PiHole in your setup doing stuff.
>
> Paul
>
Yes I have a iCloud account. Works on iTunes, works on iCloud sync
Photos & iCloud.com
..
I do not own a iPhone, I own a iPad.

Jim

....w¡ñ§±¤ñ wrote:
> Jim Dell wrote on 2/26/24 7:38 AM:
>> iCloud for Windows setup fails
>>
>> Environment:
>> Windows 10 for home 64-bit
>> Dell Studio XPS 8000
>>      12gb memory
>> Outlook 2019
>>
>> Load iCloud for Windows
>> Turn on sync for Calendars & Contacts
>> Error message: “Your setup couldn’t start because your username or
>> password is incorrect. Go to iCloud for Windows, sign out, sign back in”
>> Log out of iCloud
>> Log in to iCloud
>> Turn on sync for Calendars & Contacts
>> Same error message "Your setup couldn’t start because your username or
>> password is incorrect. Go to iCloud for Windows, sign out, sign back in”
>>
>> Things I have tried:
>> 1)    Checked that the iCloud for Outlook Add-in is active
>> 2)    Reinstalled Office 2019
>> 3)    Uninstalled & installed iCloud for Windows
>>
>> I also have a Dell laptop running Windows 10 Home 64-bit with Outlook
>> 2019 and iCloud syncing Calendars & Contacts works.
>>
>> Anybody got any hints on how to get setup to work?
>>
>> Jim
>>
>
> Did you create a primary icloud email address in your icloud account?
> Did you setup the primary icloud email address in Outlook?
> Did you setup the primary icloud email address with an app specific
> password and use that password for the primary icloud password(when
> setting up the icloud email in Outlook)?
>
>
Yes to all iCloud email addresses.
The iCloud mailbox in outlook is able to send & receive e-mails.

Jim