[REQUEST] Sync Windows Outlook Calendar with iPhone 12

[George Hurley]

For years, I resisted getting a smartphone until I found I could synchronize my Windows Outlook Calendar with an iPhone. Somewhere at the beginning of the century, I got an iPhone, and synchronization was easy - I installed iCloud for Windows on my Desktop and said I wanted to share my Calendar and Contacts List between my iPhone and Windows desktop, and it happened. A date entered on my iPhone calendar showed up on my desktop Outlook app, and vice versa

Recently, I reinstalled all of my Outlook accounts, and my calendars no longer sync. I'm using the desktop Outlook (2021) and not the Outlook.com. I installed the latest version of iCloud for Windows (it looks like the new iCloud app was released before it was finished). I told iCloud to leave everything alone except Calendars and Contacts and turned on synchronization for them. Alas, after many tries and reboots, no joy. I've found many suggestions online, but nothing works. For instance, one said to open iPhone Settings, tap Calendars, tap Accounts, tap Outlook, then toggle synchronize. But there is no Outlook account to tap. Others say it can be done by changing Registry Settings. Apple says that I can generate an app-specific password for any app not created or provided by Apple, which I did, but the password doesn't work with Outlook or iCloud - it would be nice if Apple were to explain how to use the app-specific password.

Why is it that something that was once so simple now seems near impossible? I know that Microsoft and Apple seem to be hell-bent on destroying computing as I know it, but couldn't they maybe wait a few years?

I would appreciate any suggestions.

 

[Sky-Knight]

Because it's 2024, and we don't have local datasets to synchronize anymore.

If you use Outlook on iOS and connect it to Exchange, it syncs the calendar.
If you use Apple Mail on iOS and connect it to Exchange... it syncs the calendar.

The problem isn't the feature set, the problem is the ancient mail service that doesn't communicate correctly. Think about where the calendars are located, if you're mucking around with software on any given endpoint... that won't fly anymore.

 

[britechguy]

sync outlook calendar and contacts to iphone at DuckDuckGo

DuckDuckGo. Privacy, Simplified.

duckduckgo.com

This is not an infrequent need, and it can be done.

 

[timeshifter]

Recently, I reinstalled all of my Outlook accounts

What do you mean by Outlook accounts? joe@outlook.com or a Gmail account, or a POP or IMAP account, Microsoft 365???

 

[Markverhyden]

For years, I resisted getting a smartphone until I found I could synchronize my Windows Outlook Calendar with an iPhone. Somewhere at the beginning of the century, I got an iPhone, and synchronization was easy - I installed iCloud for Windows on my Desktop and said I wanted to share my Calendar and Contacts List between my iPhone and Windows desktop, and it happened. A date entered on my iPhone calendar showed up on my desktop Outlook app, and vice versa

Recently, I reinstalled all of my Outlook accounts, and my calendars no longer sync. I'm using the desktop Outlook (2021) and not the Outlook.com. I installed the latest version of iCloud for Windows (it looks like the new iCloud app was released before it was finished). I told iCloud to leave everything alone except Calendars and Contacts and turned on synchronization for them. Alas, after many tries and reboots, no joy. I've found many suggestions online, but nothing works. For instance, one said to open iPhone Settings, tap Calendars, tap Accounts, tap Outlook, then toggle synchronize. But there is no Outlook account to tap. Others say it can be done by changing Registry Settings. Apple says that I can generate an app-specific password for any app not created or provided by Apple, which I did, but the password doesn't work with Outlook or iCloud - it would be nice if Apple were to explain how to use the app-specific password.

Why is it that something that was once so simple now seems near impossible? I know that Microsoft and Apple seem to be hell-bent on destroying computing as I know it, but couldn't they maybe wait a few years?

I would appreciate any suggestions.

That seems like an awfully complicated and convoluted path, full of pitfalls and surprises, when all you have to do is install Office for iOS. As @timeshifter asked what are you using for email.

 

[callthatgirl]

If the new iCloud download (sounds like that's what you are using) isn't working, look in the Outlook add-ins, and check for the appdev in the disabled items. Enable it. Then check the enabled add-ins and be sure iCloud is checked. Common for the product version to not turn them on or enable the appdev.

Paid products also have issues with 3rd party apps, if the above fails, then try upgrading to 365, home or business works with iCloud.

Message me if this doesn't work

 

[callthatgirl]

I really like the new iCloud download, works much better and faster than the old one. It's a good version.

 

[callthatgirl]

And you don't need to do anythign on the iPhone if your cal/contacts are default, guessing they are as they are for almost everyone unless you change the default to another type of account that syncs with the server (Gmail, Yahoo, etc.) but they won't sync in Outlook desktop without a 3rd party app. Only Microsoft Exchange the free Exchange home personal options do that (Outlook.com, MSN.com, Hotmail).

 

[George Hurley]

If the new iCloud download (sounds like that's what you are using) isn't working, look in the Outlook add-ins, and check for the appdev in the disabled items. Enable it. Then check the enabled add-ins and be sure iCloud is checked. Common for the product version to not turn them on or enable the appdev.

Paid products also have issues with 3rd party apps, if the above fails, then try upgrading to 365, home or business works with iCloud.

Message me if this doesn't work

Thanks for the advice. There was nothing in the disabled add-ins, and the icloud Outlook and Microsoft Exchange add-ins were both enabled. I don't want to upgrade to 365 because I want to own my software and not rent it. I've been retired for some time, and my calendar isn't as busy as it was, so I just enter calendar events on both my phone and in my desktop Windows Outlook. I have spent more hours trying to fix this than I would spend entering dates on both platforms for the next ten years.

When I first set up the synchronization, I was using POP3, and switched to IMAP at least ten years ago. Even though synchronization was working until recently, could this have anything to do with it?

 

[callthatgirl]

iCloud sets up it's own instance, doesn't sync with POP or any (This computer only) from IMAP. It has a completely different set of calendars and contacts. You're better off migrating the data to an Outlook.com account, then setting your iPhone to default everything to outlook.com and turn off the iCloud cal/contacts. It's a lot of work, I do it all the time and quote clients 2 hours to do (full rework of their Outlook and usually includes setting up business Exchange vs Outlook.com). It takes me 2 hours and I know what I'm doing lol, so you might have a longer battle. iCloud is a 3rd party app and will eventually you won't need it with the New Outlook. It auto sets up fine. Have you tried the new Outlook?

 

[Sky-Knight]

All software is rented, there is no such thing as owning it.

Exchange functionality comes with Outlook.com email which is free, similar with Gmail services.

As Callthatgirl suggests, pick a free service that has a working calendar and put your data in there. From there you follow that service's instructions to sync that data to endpoints.