Using older versions of Outlook for Mac for personal email and calendar
Hi,
Thanks for explaining your situation so clearly. I’m sorry you’re dealing with this losing contacts without warning and getting stuck in support loops is incredibly frustrating. Let’s try to sort this out together.
Just to help narrow things down, have you recently connected your Outlook account to a new device, app, or service like Apple Contacts, Thunderbird, or a phone sync? Or changed any sync settings that might’ve affected your contacts?
First, try checking your contacts online at https://outlook.live.com/people
Sometimes they’re still in the cloud even if they don’t show up on your device. If you see more than 13 contacts there, that’s a good sign. If not, we’ll dig deeper.
You can also check the Deleted Items folder at https://outlook.live.com/mail/deleteditems Contacts don’t have a separate deleted folder, but they might show up as messages with vCards you can restore.
If you tried importing contacts from your Mac and it didn’t work, I can walk you through exporting them properly and re-importing them into Outlook.
And if this turns out to be a sync or account issue, Microsoft might be able to help. You can go to https://support.microsoft.com/contactus choose Outlook.com, then Contacts and People, and look for the option to restore deleted contacts. or there's an option for live chat support.
Let me know what you find , I’m here to help anytime.
Warm regards,
Edward