icloud syncing calendar to Outlook

[alexsmith2709]

I've got a customer who is a little bit set in his ways and doesnt want to use Exchange Online (I am trying) and he wants to sync his calendar from his iphone to outlook. Recently i managed to convince him to use icloud to do the syncing as i dont believe its possible to do it through itunes anymore (he loved connecting his phone to his computer and syncing through itunes to outlook). Now this icloud syncing to outlook stops working every couple of days. I dont know why it happens so i get it working again and hes happy for a couple days but im not getting to the root cause.

He has an IMAP email account with IONOS which is accessed on his computer through outlook 365 and on his iphone using the mail app. The email all works well (as well as hosted email does).
The icloud calendar is setup in outlook, but then items stop syncing or cannot be deleted/edited. This happens both ways, no matter what device is used to add the entry.

I've tried removing and re-adding the icloud add-in without success. Does any one have any ideas of how i can get this reliable again as it was working fine for many months.

I recently suggested Exchange Online again and he was more open to it as hes getting so frustrated, but when i found out he had multiple email accounts for his domain and that it wasnt going to be as easy as first thought and others will be affected he put a pause on it.

 

[callthatgirl]

The icloud calendar is setup in outlook, but then items stop syncing or cannot be deleted/edited. This happens both ways, no matter what device is used to add the entry.

There a few things to check
Windows updates
Office updates
iCloud updates
AV

Then, if that fails, I tell folks that iCloud is unreliable with Outlook and to use the free outlook.com account instead. You can import/export pretty easy and then setup his iPhone with defaults to use the Outlook.com account. It's free, just has to pay you to configure and help. I quote 2 hours and get $599 for this. Trust me, you will need to redo his profile, do all the work, answer questions, help with the phone, then aftercare. It's a full 2 hour job.

 

[britechguy]

Apparently the same thing happens with iCloud, Outlook, and Contacts as well. Someone was asking about how to keep Outlook under iOS from making his Contacts read only even when he's created them there originally.

 

[callthatgirl]

More ideas
Check the disabled add-ins, if you see appdev something, enable that.
You can try uinstalling iCloud, log out first, be sure you have a backup of the calendar and contacts from Outlook first

 

[alexsmith2709]

Thanks for the suggestions. Maybe the free outlook.com account is the way to go if Exchange is a no-go.
When i was looking in the add-ins before i didnt notice a plugin like that, but i'll double check.
I'm pretty sure i reinstalled icloud which didnt help

 

[timeshifter]

tell folks that iCloud is unreliable with Outlook

This. Do it the way God intended, use Outlook with Microsoft services.

 

[alexsmith2709]

This. Do it the way God intended, use Outlook with Microsoft services.

Believe me, im trying! They guy has gone back to pen and paper at the moment and says he's loving it...if he loves it that much i dont know why he just doesnt stick with that!

 

[callthatgirl]

Tell them your price tag to do the work, he will love paperwork even more! I sometimes see clients systems and am like WOW, you're going to need 4 hours to do this, they have crap everywhere!

 

[alexsmith2709]

Tell them your price tag to do the work, he will love paperwork even more! I sometimes see clients systems and am like WOW, you're going to need 4 hours to do this, they have crap everywhere!

I'll tell them your price tag instead, its much higher than mine!

 

[callthatgirl]

The price tag is perfect, sorts out the weak.