How to fix incorrect username or password for Outlook setup in iCloud

My Outlook Calendar to iCloud worked just fine before your last rotten rework of an update. Go Backwards and try again! Your lousy coding now creates extra work time on my end to keep my work schedules updated. I didn't ask nor was I asked by you if I wanted these changes. (why fix something that wasn't broken to begin with).

Or at least give us a location to download previous version that work.

Thus far I have spent 32 hours trying to get your stuff to work. Sound angry I am.

Hello everyone,

I've been experiencing significant challenges with the software, particularly with the Outlook integration feature, which doesn't seem to function correctly. Despite carefully following all recommended steps, I now encounter a persistent issue where the iCloud window unexpectedly pops up every 5-10 minutes, disrupting my workflow. The only workaround I've found is to keep this window open continuously, which is far from ideal. Additionally, iCloud Drive fails to initialize properly.

@B0bF , I noticed you mentioned attempting a reinstallation. Have you faced similar issues post-reinstallation, or did it resolve the problems for you?

I appreciate any advice or solutions the community might offer. Thank you for your help.

Please scroll to the last post and you see nothing has worked for me or anybody else

I have had the same problem on my laptop for years.

The following fix used to work but resent Microsoft update has stopped contacts syncing again.

1. Run iCloud setup as the logged-in iCloud user.

2. Un-check the "Contacts and Calendars with Outlook" option, apply and close.

3. Run Outlook, go to File / Options / Add-ins / Manage COM Add-ins / Go...

4. Disable the iCloud Outlook addin, close Outlook.

5. Run Outlook with "Run as Administrator", disable iCloud addin as per 3&4 above.

6. Keeping Outlook open, /remove/ the iCloud addin, still as Administrator.

7. Close Outlook (may need to reboot; probably not -- feel free to try both ways).

8. Run Task Manager, close all iCloud processes if any are running (may need click "more details" and scroll down).

9. Run iCloud setup with "Run as Administrator", enter password, confirm via 2fp

10. If iCloud won't run, then it needs to be updated as part of the Windows update, and requires a reboot.

11. In which case, reboot, and repeat from step 8 above.

12. Check the "Contacts and Calendars with Outlook" option, apply and close.

13. Run iCloud setup as the logged-in iCloud user, enter password and confirm if needed.

14. Check the "Contacts and Calendars with Outlook" option, apply and close.

15. Run Outlook as administrator, go to File / Options / Add-ins / Manage COM Add-ins / Go...

16. Manually add the iCloud Outlook Add-in from the file in %ProgramData%, typically:

17. C:\ProgramData\Apple Inc\iCloud\Outlook\aplzod32.dll

18. Close options.

19. The iCloud outlook add-in toolbar icon will say "wrong password" instead of "refresh".

20. This is fine because Outlook was started as administrator and is using the wrong credential cache.

21. Close outlook.

22. Re-open Outlook as the logged-in user and it should now be happy and show "refresh".

@BObF – I’m in the same situation as you and probably just as frustrated.  I’m on win 10 and OL2019. iCloud worked for years.  But I hit this bug when I simply signed out of iCloud and tried to sign back in. My 4 other devices (iPhones and iPads) all still sync.  The 22-steps posted by @Scottgs62 gave me the same results as @Dellji.  I’ve also seen this problem discussed in several other places online but no solutions yet.

@BObF - I'm using OL2019. It was a big pain, but this is what finally worked for me:

1- Upgraded from Windows 10 to Windows 11

2- Uninstalled iCloud 15.0.215.0 but did not uninstall “iCloud Outlook” 15.0.0.215

(that’s not a typo, the rev numbers are different)

3- Installed iCloud 13.4.101.0

4- Apple’s 2FA only partially worked

5- The 2FA location verify pop-up disappeared too quick, so

6- I had to select “Send code to a trusted device”

7- I selected one, but there was no place to click, so I hit enter on my keyboard. It worked.

8- After iCloud 13.4.101.0 installed, my OL2019 contacts and calendars synced

9- Closed OL2019 and ran Windows Store Update which updated iCloud 13.4.101.0 to 15.0.215.0

10- My contacts and calendars have been in sync for over a month, but I haven’t signed out of iCloud. 

[Edited by Moderator]

@BObF - Thanks for following up with your final solution.

Did you need to re-create all of your Outlook customization and configuration settings manually or were they automatically transferred to your new 64-bit installation of Outlook?

If they automatically transferred, what method did you use for uninstalling?

I have tried all of these suggestions and have found that none of them work. 1) Switched from 32 bit to 64 bit office, 2) Removed the COM iCoud add in, 3) logged in and out of icloud, 4) Changed Apple ID password, 5) Changed account to be admin account, 6 etc ---- I have two windows clients that have this issue. No Calendar and No Contacts sync. I suspect the issue has something to do with application specific paswords.

After trying multiple suggested solutions. I found one that worked. I did the following. I Updated my MS Office from 32 bit to 64 bits AND created a completely new account on the PC. After doing this iCoud installed and had no difficlity in setting Outlook up to connect to my iCloud calendar and contacts.

I have the same issue as B0bf. It says i have the wrong password but wont let me fix it. I even unloaded icloud and reset it up but it gives me the same error. This is on my desktop. My laptop works just fine. I just need to get to a screen that allows me to fix the password so I can sync icloud calendar and emails with outlook.

My Soloution

icloud for Windows - stuck on initializing - Apple Community

Unfortunately it didn't work for me

During step 12 I got the incorrect password message

Step 19 never saw "wrong password"

step 22 don't see "refresh"