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Setup

I have two devices: a Windows 10 laptop and an iPhone. Both contain (or contained) 3 calendars, synced between Outlook 2019 and iOS via iTunes for Windows and a USB cable. These calendars were local, i.e not attached to any cloud account. They were named "Personal", "School" and "Work".

Accident

I'm not sure exactly how it happened, but I accidentally wiped the calendars' contents and names by trying to sync my contacts using iTunes. As far as I remember, I

  1. Plugged the iPhone into my laptop
  2. Opened the "Info" tab in iTunes' phone settings
  3. Enabled "Sync Contacts with Outlook"
  4. Checked "Contacts" in "Replace information on this iPhone"
  5. Clicked "Apply" and launched the synchronization

Anyway, here are the results:

  • The contents of the 3 local calendars are gone, on my laptop and on the iPhone.
  • Outlook still shows 3 calendars, with the right colors, but generic names: "Calendar", "Calendar" and "Calendar (This computer only)".
  • The iPhone shows only one calendar instead of the 3 I had, also empty, and also generically named ("Calendar").
  • An online calendar subscription I had set up on both devices separately has disappeared from Outlook, but not the iPhone.
  • Contacts haven't been synced to the iPhone, but they have survived in Outlook at least.

Backup situation

In a backup from a few days ago (when the calendars were still intact and properly synced), I found a copy of the entire C:\Users\me\AppData\Local\Microsoft\Outlook folder. In it are

  • A folder called RoamCache (the "cache" prefix makes me think this is irrelevant)
  • A file named [email protected]
  • A file named Internet Calendar Subscriptions.pst

I tried importing the .pst file in Outlook, which only added back an online calendar subscription I had set up, not my 3 personal calendars. Outlook refuses to import the .ost file, because it "is not an Outlook data file (.pst)".

I also have an iTunes backup of the entire iPhone, but I'm having some restoration problems that I will have to sort out with Apple support. Also, restoring the entire iPhone just for my calendars would be inconvenient.

Question

Are my local calendars stored in the Outlook files I backed up? If they are, how can I restore them? If they aren't, where should I look for them in my backup (hoping that this will be a location I also backed up)?

Also, if someone can tell me what I did that made iTunes delete my calendars' contents, and if it's relevant to my problem, I would be thankful.

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  • .ost files are the data files from online email servers and cannot be imported in Outlook because the file is only a copy of the emails on the email server and doesn't contain any information not found on the email server (conversely, .pst files are local data files with the main info source being the local copy, not the server's data). I'm not sure how to solve your issue, but I would recommend creating an Archive data file to ensure you always have a backup.
    – JW0914
    Dec 5, 2019 at 14:14
  • @JW0914 I read something like that in the doc, but since the other file is named “Internet Calendar Subscriptions” and my calendars aren’t that (and importing that file didn’t help), I figured the only other possibility was the .ost file despite what the doc says. I’ll be more careful with my backups next time. Would you know of any other place where Outlook keeps profile data, which could contain the original copy of local calendars?
    – Hey
    Dec 5, 2019 at 14:19
  • That's the only place Outlook keeps .ost and .pst files. For syncing info to/from the Outlook desktop program, I always recommend buying CompanionLink Pro over anything else, as I've had the same issue you've had before - if you buy the one-time license, it's fairly expensive ($130), but it's a one-time-purchase lifetime license that applies to all future updates and version upgrades (I've had it over >5yrs). It's compatible with all known services/OSes/Devices, auto-syncs and provides complete control over how the sync occurs
    – JW0914
    Dec 5, 2019 at 14:23
  • In regards to Internet Calendar Subscriptions.pst, IIRC, iTunes accesses it during the sync, so those changes are likely permanent in the .pst file. You can try seeing if the online versions of the synced calendars allow you a grace period where you can restore deleted events, and I would also check the deleted items folder of the main Outlook data Outlook.pst, which should have been auto-created upon first opening Outlook after install (File Menu > Account Settings > Data Files tab).
    – JW0914
    Dec 5, 2019 at 14:31
  • To be sure, there is no online version, they were completely local and synced via USB. The backup I am recovering from was made a few days before the accident (which I agree is permanent), so I'm surprised that these files don't seem to contain my data. I also didn't mention I added several email accounts today, so maybe the calendars could be lost in one of the data files? I'm still not completely sure I get how Outlook data files work. Thanks for your help in any case.
    – Hey
    Dec 5, 2019 at 14:42

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