Problem with Outlook and Sync with Apple devices

Question

I just noticed after the last  update I lost the ability to sync my PC with my iPhones, Contacts and Calanders on my iPads & iPhone and iPads. I no longer see the Blue icon  with the curved arrow on my Outlook on my PC. That was the “refresh” button if you wanted it to update immediately.

On my devices I use the “Family” calendar to sync with all my devices.  

How do I get it back? I looked at the Microsoft Store, and I do not see that icon anymore.

Any help would greatly be appreciated…..

 

Thanks,

Tony

Answer 1

I called Apple for an advisor to help. Here's what he did to fix my problem:

1. Open Outlook and go to File>Add-ins>Activate iCloud Outlook Add-in if it not active
2. Problem Solved....

I thought it was already done as a basic step :(

I am sorry but I am glad it is all sorted now!

Answer 2

@Anthony Mirando said

The problem is that if I put a new appointment in calendar or contacts on my PC, they do not appear on any Apple product

As I understand it your basic problem is that your PC Outlook Classic Calendar is not syncing with your iCloud Calendar.

If so, the mail accounts in Classic Outlook have nothing to do with it. iCloud Calendar and Contacts sync is handled differently that mail.

If you run the iCloud for Windows program on your PC and click [Account Details] do you see that your iCloud for Windows is connected to your iCloud account?

Is the iCloud for Windows "Calendars and Contacts" switch "On" (Green) and it shows that it is syncing?

If the "Calendars and Contacts" switch is not "On" when you switch it ON do you see a success dialog?

If not, a screen shot of the error message please.

Clarification - iCloud for Windows does not sync your main Outlook Calendar with iCloud. It only adds a new iCloud Calendar to your Classic Outlook. Any events you put on the iCloud Calendar should then sync to any other iCloud devices.

Answer 3

I want to thank all who helped me with this problem about syncing. I think I failed to fully explain the situation. The problem I have, simply put, is just my PC not connecting with my Apple products. Those products are:Tony iPhone

Tony iPad

Wife’s iPhone

Wife’s iPad

Under “Calendars” on all units I show under “iCloud”>Family and under “Other”>Us Holidays and Birthdays. Also “Show Completed Reminders is “on”

 

I am running Microsoft Exchange Family version. I have  iCloud on my PC.

The problem is that if I put a new appointment in calendar or contacts on my PC, t__hey do not appear__ on any Apple product listed above.

Also, your suggestion about iCloud

I went to the Mail App and it shows 2 accounts.

One is “iCloud” and it shows “on” on Use on this iPhone. Account info shows an old email that I do not use. It’s one that original had to use on the 1st iPad when it was introduced. Do I need this?

The 2nd account is Exchange,. It shows all 5 options as “on”.

All of the above on 2 & 2 have to do with my (Tony) units. What, if anything, do I need to do to my wife’s units to connect?

 

I do hope I covered all topics so that I can go back the way it was before they deleted the old App.   

Thanks so much for the help….

Tony

Answer 4

Hi there,

Is iCloud working properly on the device?

Set up iCloud Calendars and Contacts in Outlook on your Windows computer

https://support.apple.com/en-in/guide/icloud-windows/icwa12798053/icloud

Open the iCloud app, sign in with your Apple ID, and check the box to automatically sync Contacts, Calendars, and Tasks with Outlook.

Restart Outlook. The add-in is typically active by default, but you can verify its status by going to File > Options > Add-ins.

Troubleshoot (if it isn't syncing): Close Outlook, open the iCloud app, uncheck the sync boxes, click Apply, recheck them, and click Apply again.

I’m eager to hear back and work together to find a solution.

Standard 3rd party link disclaimer:

There may be links to non-Microsoft websites that provide accurate and safe information. Watch out for ads on websites frequently classified as PUP (Potentially Unwanted Products). There is no need to buy paid products to fix your computers, as they sometimes do more harm than good.

Answer 5

The blue curved-arrow “refresh” icon and direct device-to-PC sync used previously are no longer available in the current Outlook experience. Calendar and contacts sync now rely on server-based synchronization (Exchange ActiveSync or similar), not on a manual refresh button or direct cable/iTunes-style sync.

To restore calendar and contacts syncing across PC, iPhone, and iPad:

1. Ensure the account is set up with a protocol that supports calendar/contacts
   • IMAP and POP only sync email. They do not sync calendar or contacts.
   • The account must be added as an Exchange/Exchange ActiveSync (or Outlook.com/Microsoft 365) account on all devices.
2. On iPhone/iPad (built-in Mail/Calendar/Contacts apps)
   • If the account is currently added as IMAP/POP, delete it and re-add it as Exchange:
     • Go to iOS Settings → Mail → Accounts → select the account → Delete Account.
     • Re-add the account and choose Exchange when prompted.
     • Follow the prompts so the device uses Exchange ActiveSync, which supports calendar and contacts sync.
3. On Outlook mobile app (if used)
   • Verify calendar and contacts sync is enabled:
     • In Outlook mobile, open Calendar, tap the three lines (menu), and ensure the calendar for the account is selected.
     • For contacts, ensure the app has permission:
       • iOS: Settings → Outlook → enable Contacts and Background App Refresh.
       • Android: Settings → Applications → Outlook → enable Contacts, then in Outlook → Settings → account → Sync Contacts.
4. If calendar/contacts still do not sync
   • In Outlook mobile: Settings → tap the account → Reset Account.
   • If that fails, delete and re-add the account in Outlook mobile using the Exchange/Outlook.com option, not IMAP.
5. If using iOS Mail or Samsung Email instead of Outlook mobile
   • iOS Mail: delete and re-add the account as Exchange so calendar and contacts can sync.
   • Samsung Email: Settings → Accounts → Exchange → tap the email address → ensure Sync Calendar is enabled. If the account is IMAP, remove it and re-add as Exchange ActiveSync/Exchange.

Once the account is configured as Exchange/ActiveSync everywhere, the “Family” calendar and other server-based calendars will sync automatically without a manual refresh button.

---

References:

• Can't sync calendar and contacts with my phone or tablet
• Troubleshoot Outlook mobile issues
• Set up the Outlook app for iOS