Outlook 2016 Outlook-2016 and iCloud for Windows - Problems

Vince

Senior Member
Outlook version
Outlook 2016 32 bit
Email Account
POP3
Since this is the best place on the Internet to discuss Outlook and iCloud for Windows integrations, I thought I would start a thread. Not only to help me through my current problems, but to share my experience with others looking for tips and help. While I still have my Mac-Mini-2012 (that I bought to experiment with iOS development) my main desktop/laptop computing environment is still Windows. However, myself and the family use Apple iPhones, iPads, watches, etc. … and I’m really liking the Apple Ecosystem and iCloud.

TL;DR = So here I am now with neither version working with Outlook-2016. I tried a clean-install of both iCloud for Windows versions. The v11 will not install completely, and the old v7 is malfunctioning.

Intel-i7 with 16gb RAM
Windows-10 Pro (64-bit) v1909
Outlook 2016 (Microsoft Office 2016 Pro - 32bit)
iCloud for Windows v7.21
Google Chrome v86.x 64-bit

Apple-ID with two-factor authentication Enabled
- App Specific password for Outlook-2016
- On my iPhone-SE-2020, and iPad … everything syncs to iCloud except iMessage
- Since old iPhone-5, I like having “master-copy” of my Contacts in iCloud (for use everywhere).
I’ve been using Microsoft Office Pro and Outlook since Office-2000. During each upgrade, I brought my PST file forward. I file important emails and items in appropriate folders and try to save-out attachments to local drives (instead of inflating my PST file). Before I started using the Apple Ecosystem, I kept my master-copy of Contacts inside Outlook. I was even able to get a (one way) copy to various PDAs and flip-phones. Ah, the good-old-days.

I had a long (fairly) trouble-free run with Outlook-2007 and iTunes/iCloud for Windows. I just used Apple Update as required. Sure, there were a few glitches and sometimes it felt like it was all “barely working” but still, it worked, meaning … Contacts, Tasks/Reminders synced in three directions (Windows Outlook, iCloud.com, and iPhone/iPad). The other iCloud stuff like Chrome Bookmarks and Photos seemed to also work acceptably. That was on Windows-7 Ultimate (64-bit) and then upgraded to Windows-10 Pro (64-bit). Had an iPhone-5, then a iPhone-5s until recently.

In 2019 (around iCloud for Windows v7.9) the release notes said that Office-2007 was no longer supported. While I had Office-2010 on my laptops, I upgraded past it to Office-2016-Pro/Outlook-2016. This was a normal installable version, activated with a serial-key-number. I installed the 32-bit version because I thought it was required so that programs like iCloud/Nuance Power PDF would still plug-in and work. It was fairly painless and worked. Like usual, I made some notes to documented highlights of the successful process.

I’ll also mention that I recently went ahead and turned-on iCloud Photos and started paying Apple $36 a year for 200gb storage. This was mainly for pics/vids. Before, PhotoStream alone was not so reliable and would often quit sending/syncing to my main Windows machine. So now, everything gets saved in iCloud. Occasionally, I download sets of pics to my local storage/NAS and delete them from iCloud Photos storage to free-up space.

So, a few months ago I noticed that my Task/Reminders were not appearing inside Outlook-2016 any longer. And since iCloud Notes ( a really handy feature) were never really supported in Outlook anyway … I started using icloud.com (in a Chrome browser window) for Notes AND Tasks.

A week or so ago, while saving an edited one of my (312) Contacts, the record’s window said Not-Responding and Outlook-2016 locked-up and crashed. After rebooting, I noticed my iCloud Contacts were no longer syncing with Outlook reliably. After a reboot, it seemed to work once/twice and then fail/lockup Outlook. I tried the usual fixes (un-check/re-checking Outlook in iCloud Settings, Sign-Out my Apple-ID, etc.) but nothing really helped.

When I tried using Apple Software Update to check-for an updated version, after a long try, it eventually errored-out saying “The Apple Software Update server could not be found”. Yet, all looks good here:

When I went to Apple’s official iCloud for Windows page, instead of finding a direct download for v7.21, it now says that users on Windows-10 should use the Microsoft Store v11.x. It also said that the old v7.x version was only for Windows-7/8. Even though I remember reading that Diane said we can keep using the latest v7.x version, Apple is specifically saying NOT to use it any more. I was running out of options.

I tried installing the (Microsoft Store) iCloud for Windows v11.x . The Task-Tray settings look much like the old version, but there are some changes and even architectural differences. It seemed to install and work UNTIL I turned on the Outlook syncing (the feature I actually need). It seems that this feature requires a separate module. But this companion App would never install completely. It said to go to Settings/Apps and Repair, but that never helped. Here is part of the error-report:

-------------------

iCloud Setup for Outlook Error Report (v6.3.2.0) - Error: 0x8004010F: ZebraMapiCopySession::CanCreateZebraStore: CreateMessageService failed

iCloud for Windows did not install properly. To repair it, you need to go to Apps and features, select iCloud Outlook from the app list and click Modify.
When prompted, click on Repair. <a href="repair">Open Apps and features…</a>

Error: 0x8004010F: DataProviderRegistered
Error: 0x8004010F: ZebraMapiCopySession::CanCreateZebraStore: CreateMessageService failed

AppleOutlookDAVConfig version: 6.3.2.0
Windows version (10.0.18363): (build 18363), 64-bit
Local app data directory test: Pass
Temp directory test: Pass
Account GUID: B7560C9A-52C1-4AD4-9084-DAE9186C2844
Cache Size: <Not found>
REG read HKCR\Outlook.Application\CurVer -> (Default): "Outlook.Application.16"
REG read HKLM\Software\Microsoft\Office\16.0\Outlook -> Bitness: "x86"

---------------------

I tried several things, like:
- Rebooting, Uninstall v11.x, clean-installing it fresh
- Cleaning-out any remnants inside Outlook (iCloud Folder, iCloud email-accounts/data-files, etc.). I even tried a (online/long-running) Repair Install of Office-2016 Pro. BTW, this surprisingly de-Activates it and you have to re-enter your serial-key. Anyway, nothing worked. I Signed-out Apple-ID (and let local data delete). Uninstalled this new v11.x (since it will not even install completely) and deleted Chrome extension once again.

So, about this time … while Outlook is still receiving emails from my multiple POP3/IMAP accounts … I have NO CONTACTS AT ALL.


So, I found the old v7.21 standalone installer on the Windows-8 page.
Apple-ID already Signed-out (and no iCloud for Windows currently installed).
Rebooted fresh and clean-install on my Windows-10. It went more like I remember it.
It installed without error. I can see my Contacts, the new iCloud Outlook COM Addin , the 2-extra data files, and the IMAP email account for the Apple-ID.
I’m back to the original problem with v7.21 that is locks-up Outlook-2016 when trying to save Contact edits and crashes-down. Contacts are also (obviously) not syncing.
The iCloud-Settings TaskTray app is also not even working.
When I try to open it, there is a spinning circle next to Apply button, and while the options above are greyed-out, you can see that the Outlook option is completely missing.
After several minutes, it finally says “An error occurred during authentication. Please try again”. You click Close button and app exits.
Apple Software Update program still says ““The Apple Software Update server could not be found”. It still says that, even though Apple’s status page says all their cloud-based services are green/up/working.

Anyone have any ideas on how to proceed ?
 

jessewalter375

Senior Member
Outlook version
Outlook 2019 64-bit
Email Account
Exchange Server 2013
Try this :-
Select the File menu.
Click Options in the left panel.
Click Add-ins in the left panel of the Outlook Options window.
Look at the list of add-ins in the Active Application Add-ins section.
Select the iCloud Outlook Add-in checkbox, then click OK.
Restart Outlook.
 

Vince

Senior Member
Outlook version
Outlook 2016 32 bit
Email Account
POP3
Try this :-
Select the File menu.
Click Options in the left panel.
Click Add-ins in the left panel of the Outlook Options window.
Look at the list of add-ins in the Active Application Add-ins section.
Select the iCloud Outlook Add-in checkbox, then click OK.
Restart Outlook.

Yes, the iCloud Outlook Addin is installed and Active. Everything else in Outllook-2016 seems to auto-config properly as well.
Version 7.x works initially after clean-install (so my Contacts from iCloud storage get imported in initially).

Do you run iCloud for Windows on your Outlook-2019 (64 bit)? If so, which version works for you ?
 
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