As of version 15.x.x, iCloud for Outlook appears to be permanently broken when synchronizing contacts and calendars.  The previous steps posted in “iCloud for Outlook Incorrect Username or Password” no longer work. As per a comment by @MarMD in that thread, 64-bit office is the solution.

Some people are able to fix the issue simply by upgrading to 64-bit office.

If that doesn’t work on the first try, the solutions below include additional steps to make it happen.

(We had one PC just work, one required a few additional tweaks in Solution A, another required the full battery of steps in Solution B).

Please note that both lists below are solutions, /not/ recommendations — please decide for yourself.

        – Mike

——————————————————————————————————-

SOLUTION A:  64-BIT OFFICE — WITH A FEW INSTALLATION TWEAKS
This usually works, and ran fine the first time on one of our PC’s.

1. Back up your current contacts and calendars from Outlook and from iCloud in Outlook to .pst files
2. Remove all 32-bit Office installations, including msAccess runtimes
     (msOffice installers insist upon 32-bits if there are any 32-bit Office components installed)
3. Reboot
4. Install 64-bit Office including Outlook
     To force this, you may need to specify a config.xml file
     See the attached .xml and .bat files show examples on how to specify the bits for the

     installation, as well as how to exclude specific Office applications like Lync and Groove.
     Note: these are examples to play with, not a full tutorial
5. Reboot.
6. Install iCloud, but do NOT enable any features yet
     This includes Outlook/Calendar/Contacts integration in the final step of the installation wizard.
7. Open iCloud.
8. Turn on Calendars and Contacts
9. Follow the steps in the wizard
10. If there’s no error, go to step 12.
11. If there’s an error, including any of the following, go to SOLUTION B.
     – Setup can’t continue because outlook isn’t configured to have a default profile
     – Incorrect username or password
     – iCloud outlook repair required
12. If you open Outlook at the iCloud ribbon section shows on these ribbons, click Refresh
     – Home ribbon
     – iCloud ribbon
13. If refresh works, celebrate, you’re done!
14. If the iCloud ribbon sections don’t show, continue.
15. Go to File -> Options -> Add-ins -> Manage: COM Add-ins -> Go…
16. If iCloud Outlook Add-in is available, but un-checked, check it.
17. If the iCloud Oudlook Add-in does not show, click Add… and pick it from:
        %ProgramData%Apple InciCloudOutlookaplzod6432.dll (generic path, should work)
        C:ProgramDataApple InciCloudOutlookaplzod6432.dll (typical path, might work)
18. Enable the iCloud Outlook Add-in
19. Re-start Outlook
20. If all works, now enable iCloud Photos, Drive, and other features
      (waited until now for other features just in case we had to sign out of iCloud while

      debugging, which removes all iCloud content and settings from the computer)

——————————————————————————————————-

SOLUTION B:  64-BIT OFFICE — WITH ADDITIONAL FOLDER PERMISSIONS
This was required on a PC that just didn’t want to cooperate.

It’s not pretty, and requires admin privileges, some freeware, and some tech experitise. But it worked.

1.  Go through steps 1-10 in Solution A
2.  Install Nirsoft’s Advanced Run utility and 7-zip multi-archive software, both non-adware freeware
3.  Run Advanced Run
4.  Choose 7-zip’s file manager: 7zFM.exe for Program to Run
5.  Run as… TrustedInstaller
6.  Navigate to the iCloud master folder in %programFiles%WindowsApps
      As of the date of this post, with iCloud 15.0.215.0:
        C:Program FilesWindowsApps

        AppleInc.iCloud_15.0.215.0_x64__nzyj5cx40ttqa
7.  Right-click on the iCloud folder and choose properties -> security -> advanced
8.  Add localPCAdministrators to permissions, full control, for this folder, subfolder, and files
9.  Add the current user to permissions, full control, for this folder, subfolder, and files
      Note: step 9 is required even if the current user is an admin. No idea why.
10. Apply
11. Close iCloud and reopen
12. Turn on Calendars and Contacts
13. Follow the steps in the wizard
14. This should now work, in which case go to step 12 in SOLUTION A above
       If not…
15. Close iCloud
16. In the iCloud application subfolder, manually run iCloudOutlook64.msi
      As of the date of this post, with iCloud 15.0.215.0:
        C:Program FilesWindowsApps

        AppleInc.iCloud_15.0.215.0_x64__nzyj5cx40ttqa

        iCloudiCloudOutlook64.msi
17. Run iCloud again
18. Turn on Calendars and Contacts
19. Follow the steps in the wizard
20. This should now work, in which case go to step 12 in SOLUTION A above
If not… I really have no idea

GOOD LUCK!

​As of version 15.x.x, iCloud for Outlook appears to be permanently broken when synchronizing contacts and calendars.  The previous steps posted in “iCloud for Outlook Incorrect Username or Password” no longer work. As per a comment by @MarMD in that thread, 64-bit office is the solution. Some people are able to fix the issue simply by upgrading to 64-bit office. If that doesn’t work on the first try, the solutions below include additional steps to make it happen.(We had one PC just work, one required a few additional tweaks in Solution A, another required the full battery of steps in Solution B). Please note that both lists below are solutions, /not/ recommendations — please decide for yourself.         – Mike ——————————————————————————————————-SOLUTION A:  64-BIT OFFICE — WITH A FEW INSTALLATION TWEAKSThis usually works, and ran fine the first time on one of our PC’s. 1. Back up your current contacts and calendars from Outlook and from iCloud in Outlook to .pst files2. Remove all 32-bit Office installations, including msAccess runtimes     (msOffice installers insist upon 32-bits if there are any 32-bit Office components installed)3. Reboot4. Install 64-bit Office including Outlook     To force this, you may need to specify a config.xml file     See the attached .xml and .bat files show examples on how to specify the bits for the     installation, as well as how to exclude specific Office applications like Lync and Groove.     Note: these are examples to play with, not a full tutorial5. Reboot.6. Install iCloud, but do NOT enable any features yet     This includes Outlook/Calendar/Contacts integration in the final step of the installation wizard.7. Open iCloud.8. Turn on Calendars and Contacts9. Follow the steps in the wizard10. If there’s no error, go to step 12.11. If there’s an error, including any of the following, go to SOLUTION B.     – Setup can’t continue because outlook isn’t configured to have a default profile     – Incorrect username or password     – iCloud outlook repair required12. If you open Outlook at the iCloud ribbon section shows on these ribbons, click Refresh     – Home ribbon     – iCloud ribbon13. If refresh works, celebrate, you’re done!14. If the iCloud ribbon sections don’t show, continue.15. Go to File -> Options -> Add-ins -> Manage: COM Add-ins -> Go…16. If iCloud Outlook Add-in is available, but un-checked, check it.17. If the iCloud Oudlook Add-in does not show, click Add… and pick it from:        %ProgramData%Apple InciCloudOutlookaplzod6432.dll (generic path, should work)        C:ProgramDataApple InciCloudOutlookaplzod6432.dll (typical path, might work)18. Enable the iCloud Outlook Add-in19. Re-start Outlook20. If all works, now enable iCloud Photos, Drive, and other features      (waited until now for other features just in case we had to sign out of iCloud while      debugging, which removes all iCloud content and settings from the computer) ——————————————————————————————————-SOLUTION B:  64-BIT OFFICE — WITH ADDITIONAL FOLDER PERMISSIONSThis was required on a PC that just didn’t want to cooperate.It’s not pretty, and requires admin privileges, some freeware, and some tech experitise. But it worked.1.  Go through steps 1-10 in Solution A2.  Install Nirsoft’s Advanced Run utility and 7-zip multi-archive software, both non-adware freeware3.  Run Advanced Run4.  Choose 7-zip’s file manager: 7zFM.exe for Program to Run5.  Run as… TrustedInstaller6.  Navigate to the iCloud master folder in %programFiles%WindowsApps      As of the date of this post, with iCloud 15.0.215.0:        C:Program FilesWindowsApps        AppleInc.iCloud_15.0.215.0_x64__nzyj5cx40ttqa7.  Right-click on the iCloud folder and choose properties -> security -> advanced8.  Add localPCAdministrators to permissions, full control, for this folder, subfolder, and files9.  Add the current user to permissions, full control, for this folder, subfolder, and files      Note: step 9 is required even if the current user is an admin. No idea why.10. Apply11. Close iCloud and reopen12. Turn on Calendars and Contacts13. Follow the steps in the wizard14. This should now work, in which case go to step 12 in SOLUTION A above       If not…15. Close iCloud16. In the iCloud application subfolder, manually run iCloudOutlook64.msi      As of the date of this post, with iCloud 15.0.215.0:        C:Program FilesWindowsApps        AppleInc.iCloud_15.0.215.0_x64__nzyj5cx40ttqa        iCloudiCloudOutlook64.msi17. Run iCloud again18. Turn on Calendars and Contacts19. Follow the steps in the wizard20. This should now work, in which case go to step 12 in SOLUTION A aboveIf not… I really have no idea GOOD LUCK!   Read More

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