Outlook 2021 Outlook-2021 (64-bit) and iCloud-for-Windows v13.0 - It Works Good.

Vince

Senior Member
Outlook version
Outlook 2021 64 bit
Email Account
POP3
So, I just got finished upgrading my Microsoft Office Pro 2016 (32-bit) with Outlook-2016 (32-bit) and iCloud-for-Windows v7.21
to
Microsoft Office Pro 2021 (64-bit) with Outlook-2021 (64-bit) and the latest iCloud-for-Windows v13.0 (from Microsoft Store)

TL;DR – It was a fairly easy install, and everything is working fine.

I took detailed notes, but here are the abbreviated directions:

I documented my Outlook Profile (and related things). Also, my current iCloud-for-Windows settings.
I did a Full-System Backup of my Windows-10 Pro (64-bit) system (I like using Macrium-Reflect).
Note 1: I only have one local Contact setup in Outlook. Its name is “Contacts are in iCloud”.
Note 2: I use iCloud Photo Library (and occasionally off-load photos and videos to local storage).

Signed-out of iCloud-for-Windows v7.21 – I let it delete any local files (my Contacts are safe, up in the iCloud)
Uninstalled iCloud-for-Windows v7.21.
Uninstalled Microsoft Office Pro 2016 (32-bit) – You have to if you want to install a newer 64-bit version

Installed Microsoft Office Pro 2021 (64-bit) with Outlook-2021 (64-bit). Looks like it does a Full-Install of all apps.
Tested apps like Word and Excel – All working fine.
Started up Outlook 2021 (64bit) for the first time.
- I find that everything has already been automatically migrated back-in (Data-Files, Profiles, Accounts, etc.)
- Except, no iCloud Addin or Contacts yet (of course).
- Outlook checks all my email accounts with no POP3 or IMAP errors. You can catch-up on your emails now if you need to.

Downloaded and installed iCloud-for-Windows v13.0 (from the Microsoft-Store)
Started here: Download iCloud for Windows
- It installed without errors.
Run iCloud (for Windows) and login with Apple-ID (like always before).
Everything is basically the same, but there are some new options.
My Settings: iCloud Drive, Photos (all on), Outlook (Mail, Contacts, and Calendars), Bookmarks (Chrome only)
Click Apply. It configs Chrome and Outlook with little intervention required. Small change to Photos.

Open Outlook-2021 (64bit)
- iCloud Addin and your Contacts (from iCloud) are back.
- Contacts are syncing in both directions (like with your iPhone or iCloud.com)
- I dragged the "Contacts are in iCloud" Contact back into my local "My Contacts" folder.

iCloud-for-Windows v13.0 was an easy install and is working with Outlook-2021 (64bit) just fine.

I have a Mac-Mini (mainly for iOS development) but I prefer Windows computers for everything else (just always have).
However, we are also heavily invested in the Apple ecosystem (most of our personal computing devices are Apple-based).
I “live in” Outlook (and have for about 20 years now). I’m so glad to get all this updated and working again.
I hope this helps someone.

P.S. Now, on to do the wife’s Windows-10 computer. :)
 
Last edited:

Diane Poremsky

Senior Member
Outlook version
Outlook 2016 32 bit
Email Account
Office 365 Exchange
I have a Mac-Mini (mainly for iOS development) but I prefer Windows computers for everything else (just always have).
However, we are also heavily invested in the Apple ecosystem (most of our personal computing devices are Apple-based).
That sounds like me. :) I updated some certification materials for LinkedIn and needed the information to be valid in either windows or mac. So I retired my hackintosh and got a macbook with an m1. Sweet little machine... but I'm constantly hitting control+c and then have to redo it using command+c. <g> I tried remapping the keys, but found it more annoying. If only they could agree on key placements...
 

Vince

Senior Member
Outlook version
Outlook 2021 64 bit
Email Account
POP3
1. got a macbook with an m1. Sweet little machine...

2. but I'm constantly hitting control+c and then have to redo it using command+c. <g> I tried remapping the keys, but found it more annoying. If only they could agree on key placements...
1. Nice. That new M1 (and the new machine with it) look/sound pretty good. Apple is definitely on some good footings now-days.

2. That would be to easy. :) Wasn't Apple's motto "Think Different" for a while? Yeah, I have a dedicated BootCamp partition on mine (still an Intel-based one). You definitely have to switch gears when using the keyboard.
 

Vince

Senior Member
Outlook version
Outlook 2021 64 bit
Email Account
POP3
Hey, I think I missed a step on my Outlook-2021 Install.

For my Contacts ... I have my 1-(dummy) contact in My Contacts, and 357-contacts in my iCloud Folder ... however, when I go to write an email, I can't get my Names and Email Addresses to appear for To, CC, BCC (like before). I thought it just pulled those from the Contacts.
 

Diane Poremsky

Senior Member
Outlook version
Outlook 2016 32 bit
Email Account
Office 365 Exchange
There are two addressing "things" -

1. the autocomplete list - after you send a mail, the address is added to the autocomplete list and comes up when you start typing names in the to field.

2. clicking To to see the address book - If you are using iCloud, you need to set it as the default address book. Open address book from the ribbon, then Tools > options. Set the iCloud to show first at the bottom of the dialog.
 

Vince

Senior Member
Outlook version
Outlook 2021 64 bit
Email Account
POP3
There are two addressing "things" -

1. the autocomplete list - after you send a mail, the address is added to the autocomplete list and comes up when you start typing names in the to field.

Yes, that is working, but I need them all. IIRC, before it was any iCloud Contact with a valid email address entered into it's record.

I'll check item #2 and let you know.

BTW, thanks for the quick reply.
 

Vince

Senior Member
Outlook version
Outlook 2021 64 bit
Email Account
POP3
There are two addressing "things" -

2. clicking To to see the address book - If you are using iCloud, you need to set it as the default address book. Open address book from the ribbon, then Tools > options. Set the iCloud to show first at the bottom of the dialog.

Thanks. That worked. Also, your Article was a big help.

So, people following my directions above, also need to do this procedure to get your Address-Book setup properly.

I will say, it's a little "fiddley" meaning, it's hard to boil-it-down to the simple steps for documentation. Why?
a. While the Address-Book looks familiar, what you see while addressing an email is apparently not the full Address-Book (with the Options menu).
b. You select from Contacts or Contacts. I tried to make these unique names, but either Outlook or iCloud would not let me (the names changed, but they kept reverting back instantly to old/generic names). But like the Article says, you just go back and select the other one.
c. Not complaining in the least, but it looks like maybe the Article was written for a slightly older version of Outlook. But don't let that stop anyone from using it for Outlook-2021, because it is totally relevant (and you will easily figure it out).

Thanks again. This is truly the best place on the Internet for advanced Outlook users.
 

Vince

Senior Member
Outlook version
Outlook 2021 64 bit
Email Account
POP3
So, now that I've got my emails sent out and had some time to take a closer-look, it's not really hard (or fiddley) at all.

Setup Address Book in Outlook-2021 for iCloud for Windows

Open Address Book (with Tools menu being available)
- On the Standard toolbar, click Address Book icon
- On the main Outlook Screen, press Ctrl-Shift-B.

Click Tools, and then click Options. The Addressing options appear.

The “When sending email” setting is the auto-complete feature (when manually addressing an email).
- Set to the “Contacts” that contains your iCloud ones (if there are two, maybe the 2nd one).
The “when opening the Address-Book” is what shows by Default.
- Set to the “Contacts” that contains your iCloud ones (usually the 2nd one).
Now, when you click the To or CC buttons (to address an email) , the names and addresses for your iCloud Contacts will show.

Remember, I only have one local Contact setup in Outlook. Its name is “Contacts are in iCloud”. All my other 350 Contacts are in the iCloud. That way, all my Contacts are in my iPhone and everywhere else.
 

Vince

Senior Member
Outlook version
Outlook 2021 64 bit
Email Account
POP3
OK, my wife's Windows-10 Pro (64bit) machine is next.
Microsoft Office 2010 Pro 32-bit & Outlook-32bit.
- Just 2 POP3 email accounts setup (which is correct for her)
- I'm guessing her PST file is already in Unicode format.
Windows for iCloud is still the older v7.16

Pre-Upgrade evaluation doesn't look particularly good.

In Contact Folders
- My Contacts/Contacts = Just the one local "dummy" contact as normal

- iCloud
- - Contacts = I just get an error when trying to access her iCloud Contacts
- - - Seems her iCloud has fallen out-of-sync/offline/whatever-you-call-it and she never told me.
- - Secure Mail = Another Error . I think this is an old Work-BYOD remnant she no longer needs (recently retired)

She does have 100's of Contacts in the iCloud (as revealed on her iPhone/iPad) and they are fine.

Her Outlook.PST file is 16gb.

Before doing the upgrade,
should I try to dwindle down the PST file to a more manageable size by:
- deleting some thousands of old emails in her Inbox
- "save-out attachments" (pics and PDFs) from old emails and delete them inside Outlook

Or, just do the upgrade and hope for the best?
Also, do you think the "broken" integration between Outlook and iCloud is going to be a problem with getting everything uninstalled?
 

Vince

Senior Member
Outlook version
Outlook 2021 64 bit
Email Account
POP3
So, working together ... we deleted a bunch or emails, and saved-out and deleted a bunch of email attachments.

After I re-Compacted the PST file, it is down to 5.5gb . To me, that seems much-more normal and manageable (and less likely to re-rail the migration/upgrade).

So, does anyone have any comments on the "iCloud" issues above ?
 
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