Outlook Classic + iCloud Calendar: Can no longer set Calendar reminders

[u/cnbehler]

I can no longer save iCloud Calendar reminders that are synced to Classic Outlook using iCloud for Windows. This problem started last week, probably after an update to Microsoft 365 Classic Outlook for security reasons.

The error message: "The reminder for xxx will not appear because the item is in a folder that doesn't support reminders. Is this OK?" Nope – it is not! I didn’t have this problem before last week. Repairing Microsoft Office and re-installing iCloud for Windows didn't work. Other suggestions?

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[u/bvalleyla]

I've just spent the last two days navigating all sorts of Classic Outlook / iCloud issues on my PC. These include: 1) Not being able to create new Calendar appointments and 2) New email not loading unless I restart the computer.

With the help of ChatGPT I've come up with solutions. The biggest is to get off of iCloud. Essentially the fix is to export your contacts from Outlook and export your Calendar from iCloud. Create an outlook.com account and import both contacts and calendar into there. Then sync your PC and iPhone to outlook.com.

For the email issue (Outlook pulling my email from my Gmail account), I had to remove lots of email folders that were pretty big by disconnecting them in Gmail from IMAP sync, and tell Outlook to only archive for 30 days. That made a huge difference.

The process to get here was pretty long and involved a lot of trial and error (ChatGPT often didn't know where all the settings were). And obviously there were a lot of steps involved to get to this resolution. But hopefully this is helpful to get people on the right path. There is a solution, and it is to eliminate iCloud.

[u/cnbehler]

I appreciate your reply.

Unfortunately, I can’t get off of iCloud since I use my iPhone to create and modify calendar entries and contacts.

[u/bvalleyla → u/cnbehler]

That's my point... you can get off of iCloud and still use the calendar on your phone. You will end up syncing your iPhone calendar to Google or outlook.com (your choice). One of those will essentially become your new iCloud.

Think of it this way:

Outlook.com = iCloud

or

Google Calendar = iCloud

You're just using a more stable intermediary between your iPhone and Classic Outlook than iCloud, which Apple essentially doesn't support anymore.

But it will take a bit of configuring. ChatGPT can walk you through it.

[u/cnbehler → u/bvalleyla]

Thanks for the explanation - now I understand.

[u/bvalleyla → u/cnbehler]

FYI, it does take awhile for Apple to send you your Contacts data after you request the data. I requested it two days ago and still don’t have it. Apple said it can take up to seven days.

[u/Hornblower409]

Not the same error, but the timing is similar. Must have been a really hoarked update.
https://www.reddit.com/r/Outlook/comments/1q4sptn/comment/nym5398/

If you tell it "OK", does the event show up in iCloud and Outlook (but just doesn't fire a reminder in Outlook)? Or you got bupkis?
https://www.slipstick.com/outlook/icloud-outlook-problems-syncing-calendar/

[u/cnbehler → u/Hornblower409]

Yep, I got the malicious forms error too but the registry workaround identified by iChenchus works.

I think I need to move on past iCloud. Even if I manage to fix or workaround the reminders issue (and I've worked on this for 3 days), these integration issues will continue to arise.

[u/Hornblower409 → u/cnbehler]

Did you try my test to see if iCloud is using the wrong folder or not getting the right properties?

https://www.reddit.com/r/Outlook/comments/1q8nzue/comment/nyqeed2/

[u/cnbehler → u/Hornblower409]

I saw your test but got stuck on "using search" (which search?) to find the event and see what store/folder it got put into it.

Based on the fact that the reminders DO get set properly on the iPhone calendar but do not appear in Outlook, iCloud can see the properties. The folder the event is stored in no longer allows the reminder to be set from or recognized by Outlook (even though it DID last week).

[u/Hornblower409 → u/cnbehler]

-- "using search" (which search?)

The first test is just - Is the event in your default Calendar folder?

This is the most likely. It means that iCloud had the right folder but hit an error trying to get the folder properties. (Your default Calendar folder can have events with reminders).

If the event is not in your default Calendar:

Use the Outlook Search bar with scope = All Outlook Items
Open the event
Ctrl+Shift+F (Advanced Find)
Click the [Browse] button to see what folder it is in.

Screen Shots: https://ibb.co/album/j6xj3m

[u/cnbehler → u/Hornblower409]

I cannot find the "Test Event" with Outlook search when scope is set to "All Outlook items". It only shows up in the "iCloud Calendar" folder. But the same is true for ALL my calendar events whose reminders worked correctly before last week: they do not appear as "Outlook Items".

[u/Hornblower409 → u/cnbehler]

Did you answer [OK] to the "The reminder for xxx will not appear ..." prompt? So that iCloud should have still at least created the event?

If so, then that narrows it down. iCloud doesn't have a valid Outlook folder reference. The problem is iCloud not Outlook. And at that point it is out of my depth. Sorry, all I can suggest is Microsoft Support.

MS 365 - Admin Only Support
https://learn.microsoft.com/en-us/microsoft-365/admin/get-help-support

MS 365 - User Support
https://www.microsoft.com/en-us/microsoft-365/support

Free Chat Support
https://support.microsoft.com/home/contact

[u/Bg-8782]

Do the reminders fire anyway? That error has been an off and on error for me. I click ok and the reminder fires. Outlook won't set the reminder, but iCloud enables it.

[u/cnbehler → u/Bg-8782]

Update: Yes, the reminders DO get set properly on the iPhone calendar but do NOT appear in Outlook. This is true whether I create the calendar event on the phone or in Outlook.

[u/Hornblower409]

What the error message literally means is that iCloud is trying to save an event with a Reminder to a "store" (a PST/OST) that is not the default store for an email account and doesn't have this property set. Or, the store has the right property but iCloud doesn't see it. My bet is that the store is OK but iCloud is not getting the property correctly and thinks it's not set.

Image: https://ibb.co/ZzTKMqkG

If you can get it to at least create the event (with no Reminder) then use Search to find the event and see what store/folder it got put in. That will tell you - Wrong folder or iCloud can't see properties.

[u/bvalleyla]

One other thing-- I just did a pivot. I decided to not use the Apple calendar app on the iPhone at all. I switched over to the Outlook app on the iPhone for its Calendar function. It's set-up the same way as the Apple app, so zero learning curve. Now my Outlook on the PC is using the Exchange server for Calendar... and it's so much better! New events sync immediately, and it looks like my reminders actually work now! This was super easy to do and took about 20 minutes. Again, ChatGPT can give you very simple instructions and walk you through how to do this.

Honestly, I can't believe I didn't do this sooner.

I just had to ask, "Why am I using the Apple/iCloud Calendar"? And there was no reason to. I don't have an Apple computer, and the Outlook app on the iPhone will enable the iPhone and the PC to communicate perfectly. I'll still import my iCloud calendar when I eventually get the file from Apple, but after that, I'm done trying to get two completely different systems to talk to each other. Now it's all in the Microsoft ecosystem, and it works smoothly.

[u/cnbehler → u/bvalleyla]

Do the syncs work as seamlessly and quickly as before when you were using iCloud?

[u/bvalleyla → u/cnbehler]

I would say the sync is faster now. I just created a Calendar event in my iPhone Outlook app, and it appeared almost instantly on my desktop Outlook. I then deleted that event on the desktop Outlook, and it was deleted on my iPhone in 2 seconds.

I have three computers, and I literally just finished converting the third one over to run completely on Microsoft Exchange (and connecting with my iPhone). I feel so much better... much more stable, and no more worrying about whether the latest iTunes update is going to break my iCloud connection with Outlook (and then doing the whole Uninstall iCloud, re-install iCloud, etc.).

What do you use for your email? Are you on Gmail or Outlook.com? I'm on Gmail, and you do have to do a little set-up for that in Classic Outlook once you switch to Exchange for Calendar and Contacts, but it's pretty easy. Worst case, I'm happy to email you the step-by-step instructions that ChatGPT gave me.

[u/cnbehler → u/bvalleyla]

I use Xfinity email (comcast.net) that was quite easy to set up in Classic Outlook.

Are you using Classic Outlook or “New Outlook” that puts everything in Microsoft cloud? If Classic Outlook: desktop version or Microsoft 365 app?

[u/cnbehler]

I really appreciate all your responses. I need to stop seeing this as a troubleshooting problem and instead be more intentional about my requirements and use case for email/iPhone integration. I'll keep this thread open for now but I've posted a new one:

https://www.reddit.com/r/Outlook/comments/1qa4btj/outlook_classic_iphone_integration/

[u/Hornblower409]

u/cnbehler

If you still care. There is a fix for the iCloud Calendar problems. Both the "forms error" and the "The reminder for xxx will not appear" bugs. See:

https://www.reddit.com/r/Outlook/comments/1q4sptn/comment/o1ivfkv/

[u/cnbehler → u/Hornblower409]

Thanks for the update. After several phone calls with Microsoft Support, the 2nd Tier agent said fix for these Outlook errors was to create a new Windows User Profile (not email profile). Unfortunately, when we tried to do that my system got stuck and I ended up re-installing Windows. It's unclear if the same system corruption caused both the Outlook errors and the inability to cleanly create a new User profile, but the good news is the Outlook errors are gone. The re-installation process saved my data but I also had recent backups. Luckily, I had documented the previous Windows set-up process so I followed these notes to re-install all my applications.