For no reason that I know of. My icloud contacts and calendar quit upadating to outlook. I have followed the procedures of uninstalling and reinstalling icloud for windows on my pc. I have done the sync. No icloud info in outlook? What next.

If you are using non-Apple apps to access iCloud - such as Outlook - you are now required to use an 'app-specific' password in place of your normal iCloud password. In order to do this you need to set up two-factor authentication for your Apple ID, and for this you need to have either a Mac running el Capitan or above, or an iOS device running iOS9 or above.

Two-factor authentication for Apple ID - Apple Support

Using app-specific passwords - Apple Support

I had the same reaction about the app password for Outlook but it's nothing you do -- and I didn't do anything on Outlook. Yes, Windows updates probably added to the mess, but my system was fully updated when I did this and I didn't uninstall any updates. Perhaps your PC isn't currently recognized as a trusted device by Apple so I suggest you login to your Apple account (apple.com) to see if your PC is listed. My PC and my iPhone didn't show so I turned 2-step on, closed everything, restarted PC, logged back into Apple -- once the devices showed my sync started working after I started Outlook. To generate and use app-specific passwords (Outlook or any non-Apple app), your Apple ID must be protected with two-factor authentication.

It seems to be an acknowledged Microsoft issue.

Outlook known issues in the June 2017 security updates - Outlook

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Outlook's June 13 2017 Security Update

I just had a Windows update installed and my contacts and calendars from iCloud will not repopulate or download into Outlook. I reinstalled iCloud, I already had the authentication requirement, I've followed the basic steps of clicking/unclicking in iCloud and restarting Outlook multiple times. When I'm logged into iCloud, it doesn't show my iPhone (which was there before) or my PC which was also present in the past. What's next?

Thanks for posting this. I have been driving myself crazy trying to get it back...installing and uninstalling different things...I still can not pinpoint the issue or what to uninstall...I can access my contacts thru icloud but not having it in Outlook is maddening. Appreciate any insights. Thanks, Jeanine

App-Specific Passwords would not apply because the 'app' is my calendar app - it does not require a password.

I am trying to sync to outlook 2010 on the PC via iTunes and it will not update. No errors just no new information in my calendar.

Via iTunes? I'm not familiar with access to iCloud on Windows, but if you are syncing your iCloud calendar you will certainly need an app-specific password somewhere in place of your iCloud password.

I had the same problems with Outlook and iCloud -- had no idea where or what the app password applied to (yes there is one but you don't have to enter it). However, I got mine working but don't recall exactly why or which thing I did. Turning off items in iCloud for Windows (Outlook not running), then apply, then turn on and apply. Restart PC. Restart Outlook. One of the things I read which may also cause problems is that my iCloud password on windows needs to be the same as my Apple password (mine were not). I also turned 2-step verification on which was something else they said I should do.

You have to use an app-specific password in place of your normal iCloud password when you are accessing any iCloud facility with a non-Apple application, and you need to have either two-factor authentication or two-step verification on in order to do this. Evidently you managed to accomplish this.

Nothing has worked because I cannot set up a 'two step password' for either my calendar app or Outlook 2010 which is not an app. The 'two step password' answer is not correct because as far as I can see requiring a 'two step password' is not the problem. If someone out there knows how to fix this please post step by step instructions. Because I need both a calendar on my phone and computer, my phone is useless.

I have this EXACT issue. Have tried everything. And s/he is so right, it is not the two factor authentication. I read in a different forum that it has something to do with the most recent Windows Update and for me, that is when it started. I dont know what to do.

Philip,

I had/have this problem. After much investigation I was able to resolve the problem by uninstalling Microsoft Update "KB2956078". After doing this I was able to sync.

However, Microsoft insists on installing this whenever it does a scheduled update. So the problem returns. Of course you can uninstall again (which I do) but this is a pain. That's why I say "had/have".

I'm currently looking into blocking KB2956078 but I haven't determined how to do this yet. Unfortunately, until a permanent solution is found this makeshift workaround is all I have,

Anyway, I hope this helps at least a little. Let me know if you have any luck.

Gary

I fixed my problem. I do not know if this begins in the middle or the end but here it goes.

1. Close Outlook on PC (Mine is 2010)

2. Open icloud - on PC (this should prompt you to set up the two set verification I think - somewhere along the line I did set this up either through my phone or in icloud on my PC).

3. Uncheck all boxes - then re check Contacts, Calendars, and tasks. At this point icloud re-synced with my Outlook 2010.

4. re boot computer.

5. open outlook on pc - My old calendar (outlook data file) was blank but a new box 'Calendar - icloud' was there.

6. On your phone - Settings - Calendar - Accounts. I have both icloud and outlook checked.

7. On your phone - Settings - Calendar - Default Calendar. Make sure icloud is checked.

8. On your phone - Calendar App - Calendars . Make sure icloud is checked (all of mine are checked)

9. ITunes - on PC - Sync. Here, the settings had changed 'to over the air' - and both my phone and outlook on the PC had updated after the sync.

I do not know if the calendar now updates only with iTunes sync or if it is via 'push' from icloud.

I also do not know if you need icloud open and running on the PC for the updates to work...

I just installed Outlook 2016 on my wife's computer then downloaded and installed iCloud for Windows. I never got a chance to do anything about getting an app specific password because when I opened Outlook the iCloud calendar and contacts were there.

This gave me an idea, I went back to my computer removed iCloud and restarted. Then downloaded iCloud again and installed, no luck! So then I went to control panel and clicked Microsoft Office 2016, then clicked Repair. The repair gave two options, Express and Full Repair, I selected full repair and walked away. When I returned it was done and I opened Outlook and it made me login to Microsoft again (using regular not app specific password) and still no luck. Then I opened iCloud and the Mail, Calendars & Contacts icon which was missing before is now back but unchecked. I closed Outlook and checked that box and it started downloading contact and calendars. When it was done I opened Outlook and I've got my calendars and contacts back!

I have the same problem and noticed that the iCloud complmement in Outlook got desactivated.

When I check the box to activate it again, it appears in the Outlook Menu bar but it still does not work.

Any help is appreciated.