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AFAIK, OST files are for your Exchange account (your locally cached stuff). Outlook-365 is just how you pay for it (subscription instead of one-time-payment). If you are running Outlook-2021 on your local computer (like a consumer or small-business) I think you are looking for your .PST files...

These steps you are looking for are the same steps as for an Outlook migration to a new computer. Install MS-Office and Outlook (using 64-bit version now-days). Basically, just restore your old "Outlook_Data" folder that had your .PST files in it ... likely in My Documents or your Windows...

Well, how did you do? Did you ever find the Folder (with your properly-synced iCloud Contacts) ... or was is just not being created any more?

Yall are both talking about the same thing. It displays that message at the top of the email. Or ... If you right-click on a Blocked pic and allow it to download, it unblocks them all (just as if you used the top item). HOWEVER, it only does this for senders not in your Contacts. In fact, that...

So, when you click on Contacts icon (Home , icon at bottom left) ... do you not see TWO groups of Contacts? On named iCloud (Contacts - iCloud) and one named My Contacts (Contacts - Folders)? Or something close to that? Mainly, that you have two groups shown there.

I don't mean to be critical, but your terminology is poor, so it's hard to tell what you are talking about (and if anything is actually broken). The way you get iCloud for Windows working with Outlook-2021, is to properly install it inside Windows-11, configure it, and login...

Microsoft Office Pro 2021 or 2024 (Standalone version aka Lifetime License) for both of you. He will like Outlook 2021 or 2024 just fine. Google is saying support for 2021 ends in 2026 already . Hmm, I don't remember the cycle being so short (even if a new version DOES come out). Would be a...

So yeah ... I have Microsoft Office Home & Business for Mac 2021 ... on my Mac-Mini 6,1 (still on Catalina 64-bit). And while I don't use it, sure enough ... I have Microsoft Office on my iPad Pro (iPadOS 16.7.11) . Looks like it is using the MS365 subscription portal to facilitate that...

What is your definition of Legit? StackSocial is definitely legit. I pay with PayPal over there. The License-Key that you buy at StackSocial works at setup.office.com (so, it's "legit enough" to pass that primary test). I've found that it is best to retrieve the key from your StackSocial...

Because they don't know how a forum works. They don't want to read threads. They just want to ask their question, get a perfect answer, and then move on.

Your answers should be here: https://forums.slipstick.com/threads/98805-outlook-2021-64-bit-and-icloud-for-windows-v13-0-it-works-good/ or here: https://www.slipstick.com/outlook/outlook-gmails-secure-apps-setting/

Looks like I ended-up chatting with myself here on my issues. However, while I was here ... I did try to also help in some other threads. Well, hopefully some of what I typed helps others one day. I'll check-yall in a couple of years (if standalone Outlook is still around).

Well, first of all Outlook-2003 is over 20-years old, and I doubt it will run properly on Windows-11 (64 bit). Even if it does run, Microsoft doesn't support it. Secondly, if you needed an "App Specific Password" for Outlook ... I tend to get those from Apple (for iCloud) or from Google (for...

And here is how to setup Auto-Complete (when you have more than one Contacts folder). https://forums.slipstick.com/threads/101744-addressbook-search/#post-364936

Setup AddressBook Auto-Complete for Outlook. In Outlook-2021, this option must be enabled. Options > Mail > Send Messages > Use Auto-Complete. Then, go to the main Contacts screen. IF YOU HAVE more than one Folder down the left-side (meaning they are both capable of holding Contacts) ...

I might take two rules. Maybe grab the qualifying emails and move them to a unique folder. Use the 2nd-Rule to forward any qualifying emails to that person. ... something like that?

Well, my Auto-Complete works fine, and I've never clicked that little-button inside Outlook-Options. In your posted pic ... I suggest you go to the main Contacts view, and then Properties on one of the Contact Folders. On the SECOND-TAB of Properties, change one of those Outlook Addressbook...

NO. OK, I just got mine setup. When I'm trying to address a new email (in TO or CC fields) ... If I just press the r-key ... I get a whole list of 3 possibilities. I get addresses like Roger Smith, James Roberts, Rainbow Cleaners, etc. That seems correct to me. Additionally, even with two...

It worked fine. This Outlook-2021 (with iCloud for Windows v15.x) install now looks to be configured the same as the old one (as far as Accounts and Data-Files go ... well everything really). I just setup the IMAP Apple Email Account manually. It created it's own *.ost file to hold it. It gets...

You should leave characters like : and / out of filenames .