Outlook 2016 Outlook-2016 and iCloud for Windows - Problems

[Vince]

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:

Apple - Support - System Status

Status for all planned and unplanned events for Apple Services.

www.apple.com

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.

Download iCloud for Windows - Apple Support

With iCloud for Windows, you’ll have your photos, videos, mail, calendar, files, and other important information on the go and on your Windows PC.

support.apple.com

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]

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]

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 ?

 

[Vince]

So, for anyone who still uses iCloud for Windows ... what version are you running now-days and where did your get it from?

 

[Vincenzo]

I don't use it myself, but have a friend who uses it on two computers and has had lots of problems.
I found for her after lots of trial and error that downloading both iTunes and iCloud from Microsoft store worked the best.
Not sure if the Office is 64 bit though, I suspect not.

Diane prefers the Apple versions though if I remember correctly.

 

[Vince]

1. I don't use it myself, but have a friend who uses it on two computers and has had lots of problems.
I found for her after lots of trial and error that downloading both iTunes and iCloud from Microsoft store worked the best.

2. Not sure if the Office is 64 bit though, I suspect not.


3. Diane prefers the Apple versions though if I remember correctly.

Thanks for the post.

1. Hmm. Like I posted above, I never could get that v11.x to work properly. It gets hung-up on the Outlook setup part.

2. Good info. Mine being a 32-bit install is only thing I can think of to try next.

3. I think I read that also. I do kinda wonder why she is not answering me here though.

Yeah v7.21 is barely working for me these days. If I need to add a Contact or edit a Contact, I have to do it though www.iCloud.com . All I can reliably do INSIDE Outlook-2016, is to view Contacts, use them to address emails, and other "read only" stuff like that. No new ones or edits ... or it crashes down and derails.

 

[Vincenzo]

I've read that you need to have iTunes installed for iCloud to work right.

An Apple Care guy said to run your installs as an Admin.

Another thought is to be sure the aplzod file gets removed when you uninstall the old version. I can't remember where it is located.

 

[Vincenzo]

Also, and this is an odd one, when iCloud asks during installation which of your content you want to download, uncheck them all. It still downloads them all, and has made for less problems for me with this one customer's setup.

 

[Vince]

1. I've read that you need to have iTunes installed for iCloud to work right.

2. An Apple Care guy said to run your installs as an Admin.

3. Another thought is to be sure the aplzod file gets removed when you uninstall the old version. I can't remember where it is located.

1. Correct and I do also have iTunes for Windows Installed.
Additionally, Apple Update seems to be working again now (it's Server was down a while back). It now shows a minor update for iTunes.

2. Yes, I'm an Admin user on this machine. I install all software through this user-name.

3. Yes, in "Data Files" you can see where that file is stored. Additionally, I always do a "clean install" of any iCloud versions. However, next time I will make sure it's gone from Windows Explorer (even if it's already missing from Outlook Data-Files screen).

 

[Vince]

Also, and this is an odd one, when iCloud asks during installation which of your content you want to download, uncheck them all. It still downloads them all, and has made for less problems for me with this one customer's setup.

Interesting. I'll make a note of that.

I'll also mention that in addition to "clean installs" ... when I first install iCloud for Windows I don't turn-on a lot of features at first. I install the basic stuff. Get iCloud framework installed completely. Then, turn on iCloud Drive, Photos, and Bookmarks. After all that is working, then I turn-on and config Outlook. I break-it-up instead of all at once. Only Outlook is the problem.

But as you likely know, Outlook is the main reason to use this ... getting your iCloud-based Contacts into Outlook (with 2-way additions, deletions, and edits ... aka "Contacts Sync").

The other functionality (iCloud-Drive, Photos, and BookMarks-Sync) and be accomplished by other means, use iCloud.com, or just do without.

Really appreciate your help, thanks.

 

[Bill D]

@Vince - I realize you posted this 5 mo. ago, but I'm wondering if you ever solved your problem. I'm having the exact same trouble trying to install iCloud from the MS app store but Apple's iCloud for Windows (v7.21) works, even though Apple says not to use it on Win 10.

 

[Vince]

@Vince - I realize you posted this 5 mo. ago, but I'm wondering if you ever solved your problem. I'm having the exact same trouble trying to install iCloud from the MS app store but Apple's iCloud for Windows (v7.21) works, even though Apple says not to use it on Win 10.

@Bill D ,
Yes I did get this resolved. Actually, that is why I am posting today. I wanted to return and report that everything is working again. However, I'm not sure what the fix was. It just started working. I suspect an Office 2016 or Windows Update fixed it. Maybe even an Apple Update (if that is even a thing). Best I can do is list my currently installed software, and report that it all works together.

While it was "broken" I continued to use Outlook 2016, but if I needed to change/Add a Contact, I went to icloud.com and entered it there instead. It would eventually show-up in my local Outlook-2016 and I went about my business. However, one day I accidentally changed a Contact in Outlook and IT DID NOT LOCKUP trying to Sync to iCloud online. It just worked. I picked-up my iPhone, and the change was there in my iPhone's Contacts.

I also then noticed that the PhotoStream had started working a while back (lots of recent pics and videos are now in my local Folder). For a while now, I have all my Apple Devices set to use the iCloud Photo Library. I periodically move sets-of-pics from there to local storage. So, much easier to get them without having to download them first. Interesting that PhotoStream works, even though it is NOT checked in iCloud for Windows Settings ... but (for some reason) does seem to be a good indication that everything is Syncing in both directions.

That's about it for now. Hopefully, this helps you are someone searching later for tips on using Windows computers with Apple iCloud ecosystem and Apple devices (iPhones, iPads, etc.).

Windows-10 Pro (64-bit) - Currently 21H1
iCloud for Windows v7.21 (standalone-installer)
iTunes for Windows v12.11.0.26
Apple Software Updater
Google Chrome v98.0.4758.82 (64-bit)
Outlook 2016 MSO (Version 2201 Build 16.0.14827.20028) 32-bit
Office 2016 Pro (32-bit)

Various (Intel-based) Windows desktop computers and laptops
iPhone-SE-Gen2 (2020) running iOS v15.2.1
iPads (one on iOS v15.x, and another still on iOS v14.x )
Apple Watch 7