Lost Two Years Of Outlook Calendar Files

Copper Contributor


Please help me, I've lost two years of my Outlook Calendar files, and my Contact files also are gone; although, they now are found in a new I Cloud file that is set up inside my Outlook App on my desktop.


In June this year something popped up on my desktop asking if I'd like to Synchronize my Outlook with I Cloud. Being ignorant it sounded smart so I clicked to do it. When it finished all of my calendar files from January 1, 2020 through October 31, 2022 are now gone. All of my contact files were also gone, but as I said above they now reside in a new I Cloud file I never had before that was set up inside my Outlook app. I do all my health and life insurance work inside my Outlook App on my desktop, including emails and calendar appointments, and contact info. Every record of each person I've helped is recorded on those files. Now I'm missing everything I've done from January 1, 2020 through October 31, 2022. Please help me.

3 Replies



Terry thank you for trying to help me, and I deserve the criticism about back up.  My only excuse is I'm pretty old and not as savvy as the younger people.  Still I'm in a real mess that is depressing me greatly, and if these calendar files are recoverable it is going to take someone talented to take over my computer and give it a go.  


I did google the problem with this query: "my Microsoft Outlook files have disappeard after synching Microsoft Outlook with I Cloud"  Basically I saw that this is not a new problem, many people have been hurt by letting I Cloud synch with Outlook by losing all Outlook Files, but I didn't see a clear cut way to recover the lost files.  What is so weird is that all of the Outlook Contact files were gone, but only one nearly two year section of the calendar files.  My Outlook Calendar files between November 2021 and today were still there, and the ones from 2015 all the way through the end of December 2019 are still there.  How can this be; it makes no sense.  The Contact files are still all there, but they are now in an I Cloud set of Contact files that all of a sudden now appear in my Outlook App.  It is like the synch didn't complete, went bad, and it gives me hope that those Calendar files would now be showing in I Cloud if the process had simply completed.


I out of desperation paid for some online service a few days ago called Justanswer, and a guy from India took over my computer and felt the I Cloud never finished synching.  So he re did the process to synch it.  That didnt bring in the Calendar files that went missing.


Please I really need some help.  Can you help me?  Do you know someone really sophisticated who would hear this problem and know in a heartbeat how to get my calendar files back?  I'm three quarters of a century old as of last March 30, I can't stop working and get really tired daily, but I am in a  lot of difficulty heading into my Medicare work Season on October 15th if I can't access those lost files.


Carl Ehrlich


email address removed for privacy reasons

Hi Carl,

Sorry to hear that your files have been lost. If the files are still in your iCloud then you can re-sync it with your outlook.
You need to make sure each of your iCloud email subfolders are properly synced in Outlook for Mac for them to show up. Here’s how you do that:

On the top bar of Outlook for Mac, click on the “Tools” dropdown.
Click on “IMAP Folders.”
There, you’ll see all of your iCloud email folders, including the ones that are missing in your email display.
Click on each folder that you want to re-sync and then click on the green ‘Subscribe’ button on the top left. As soon as your subscribe a particular folder, the name turns bold.

Hope this helps!
Thank you for trying to help me. I'm not sure if you fully understood the problem, from your help suggestion. I don't have a Mac; I have a Hewlett Packard All In One Desktop. The files I'm missing were in my Outlook App installed on my HP Desktop. When the offer to synch I Cloud with Outlook popped up on my HP Desktop Outlook App, to the best of my knowledge I didn't even have I Cloud on my computer. I do have an I Cloud account on my Apple Phone, but I don't own an Apple computer. I've logged into I Cloud on my HP in the past, but I don't use any of its available functions like calendar or contacts etc. Maybe my I Phone communicated somehow with my HP Computer and offered to synch with it. I have no clue.

All I know is I clicked to agree to synch I Cloud with my Outlook App on my HP computer, and that is when for the first time ever any I Cloud folders appeared inside of Outlook. They were Contact Folders, and all of my Outlook Contact files were now deleted from the Outlook folder in the App and appeared in the new I Cloud Contact folders that newly appeared in my Outlook.

My biggest problem is not the contacts, since I can see them in the I Cloud folders. In fact I clicked on most of them and moved them back into Outlook folders. The problem is that almost a two year period of files in my Outlook App Calendar folders are now gone and appear no where that I can see. They no longer appear and can't therefore be opened in the Outlook Calendar which I have used for all of my work. They are gone from about January 2020 through November of 2021. So strange is all of the other months for years before January 2020 and after October 31, 2021 are still there. All of the Contact files had been moved from Outlook to I Cloud, but only a period of almost two years were deleted and totally disappeared from the Outlook Calendar I use.

Any ideas on where I might find those files and how I can get them back?