synching between Outlook 2024, and my iphone for months

Question

synching between Outlook 2024, and my iphone for months

Bonnie Lipner 0

Since my Office 2019 was no longer supported, and I lost my synching in my Outlook Calendar, I was told I needed to upgrade. I purchase Office 2024 Professional.. and have been on the phone with a number of Chats and a few Quick Assist sessions but still have no synching. The last Chat person insisted I needed to load an outlook app on my phone, and use that.. but I have an Outlook app on my phone for work, and only mostly use my personal Outlook on my PC.

EVERYTIME I need to try and get "in-app" help for the issue, I end up with instructions that don't match what's on my PC screen and I did have a tech person on Quick Assist but we got disconnected and I never got another person.

This has been going on for months.. and everytime I Chat I'm asked the same questions, and then they send me a link to in -app support that can't be followed.

Below are the two links and text sent me a couple of times by chats.

"https://support.microsoft.com/en-us/office/get-in-app-help-for-outlook-for-ios-and-android-218a22d1-9fa5-4889-b689-de1c63493243 --- Please go to https://support.microsoft.com/en-us/office/get-in-app-help-for-outlook-for-ios-and-android-218a22d1-9fa5-4889-b689-de1c63493243 and sign into their account. Click the Help tab. Everyone Select Help from the ribbon. In Help pane on the right in the search box type Contact support. Click the Yes button below the "Still need help?" prompt. Click the option to Chat with a support agent and follow the on-screen prompts."

The title on the pages is "Get in-app help for Outlook for IOS & Android.. The instruction are for phone .. not PC.

The last chat person told me that my Iphone, Outlook on PC and ICloud "CAN'T SYNCH" Strange.. I had it before and my husband has it now.

** TOTAL FRUSTRATION -- **At one point I was told I need a Microsoft OUTLOOK Support expert, but the chat's don't connect me. In prior years when I was using 2019 and I lost my synching all I did was reconnect the "Microsoft Exchange Add-In. Now that does nothing. My average call is hours long.. and one tech person left me with 22 Folders pinned in Windows Explorer. This has gone from bad to horrible and all I get when I give the chat person my Case # is "Let me read it and get the updates". In some cases they just disconnect. IF there somewhere I can get an OUTLOOK EXPERT????

Moved to Microsoft 365 and Office | Other

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Answer 1

Chloe-V 9,110 Microsoft External Staff Moderator

Hi Bonnie Lipner,

Welcome to Microsoft Q&A forum.

I’m sorry this has been going on for months. To avoid repeating unrelated steps, let’s narrow this down first.

From your description, the issue seems to be Outlook Calendar sync between Outlook 2024 on your Windows PC and your iPhone/iCloud calendar. The in-app support article you were given appears to be for Outlook mobile, so it may not match your PC screen.

Could you please confirm:

Are you using Classic Outlook for Windows or New Outlook?
Is the calendar you want to sync an iCloud calendar, Outlook.com calendar, or Microsoft Exchange/Work calendar?
Is iCloud for Windows installed on the PC and signed in with the same Apple ID as the iPhone?
In iCloud for Windows, is Contacts and Calendars turned on and applied?
In Outlook, do you see an iCloud Calendar folder?

Once I have this information, I’ll be able to suggest the next steps more accurately based on the Outlook version, calendar type, and how the account is currently being synced.

Note: Please follow the steps in our documentation to enable e-mail notifications if you want to receive the related email notification for this thread.

Bonnie Lipner 0 Reputation points

2026-07-01T15:41:20.7166667+00:00

Chloe:

Hope this information helps solve my issue.. Answers in bold.

·        Are you using Classic Outlook for Windows or New Outlook? CLASSIC

·        Is the calendar you want to sync an iCloud calendar, Outlook.com calendar, or Microsoft Exchange/Work calendar? The calendar is the calendar I get when I open Outlook .. I used to have one calendar ans somewhere along the line one of the chat/Quick Access agents added another and it split my events. When I was using Office 2019 I could synch my iphone calendar, Outlook Calendar and the icloud. Hope this helps. -- I know it can be done it works fine for my husband and he's on 2019.

·        Is iCloud for Windows installed on the PC (I'm using Office Professional 2024 as requested by the orginal Microsoft Support person, when I was told Office PRo 2019 was no longer supported.) and signed in with the same Apple ID as the iPhone? I only use one Apple sign in.. Not sure what you are asking about Cloud for Windows on my PC.. IF I want to see my cloud information on my PC, I just go to ICLOUD and sign in --

·        In iCloud for Windows, is Contacts and Calendars turned on and applied? Where would I look for this??

·        In Outlook, do you see an iCloud Calendar folder? YES See attached printscreen.

I apprecaite ALL your help, but when this was set up MANY years ago it always worked smoothly... I have been usin gOutlook for many many years and never had this kind of trouble. That's why I thought I needed a Quick Assist person to fix this. One of the last support people added an "Outlook Date File" set of folders.

Also- I used to have a round arrow to synch mail - and when that was grey it meant the "Add-in" needed to be reset.. Does that help?

I've attached what I hope may help..
Chloe-V 9,110 Reputation points Microsoft External Staff Moderator

2026-07-02T06:44:47.8033333+00:00
Hi Bonnie Lipner,

Thank you for the detailed update. I understand why this has been so frustrating, especially since the setup worked before and the instructions you received did not match your PC screen.

Please note that this is a user-to-user support forum. Moderators, contributors including external Microsoft employees cannot directly intervene in Microsoft product features or access back-end systems. Our role is limited to providing technical guidance on reported issues, requests, or ideas only.

Based on what you confirmed, you are using Classic Outlook for Windows, and you can see an iCloud Calendar folder in Outlook. For this type of setup, the key part is usually iCloud for Windows on the PC. Signing in to iCloud.com in a browser only lets you view your iCloud data online; it does not by itself create or repair the sync connection with Classic Outlook.

Please check the following on your PC:

Click Start and search for iCloud.

Open iCloud for Windows.

Confirm that you are signed in with the same Apple ID used on your iPhone.

Look for Contacts and Calendars or Calendars and Contacts.

Turn it on, select Apply, then restart Outlook.

Since you mentioned that the add-in used to be reset before, please also check this in Classic Outlook:

Go to File > Options > Add-ins.

At the bottom, next to Manage, choose COM Add-ins, then select Go.

Make sure iCloud Outlook Add-in is checked.

Select OK, then restart Outlook.

If iCloud for Windows is not installed, or if the Contacts and Calendars option is missing there, that may explain why the iCloud calendar folder appears in Outlook but no longer syncs correctly.

For reference, Microsoft’s article about this setup is here: Use iCloud for Windows to synchronize calendar and contacts with Outlook. Apple also has related troubleshooting here: If you can’t add iCloud Mail, Contacts, or Calendars to Outlook.

Disclaimer: This is a non-Microsoft website. The page appears to be providing accurate and safe information. Watch out for ads on the site that may advertise products frequently classified as PUP (Potentially Unwanted Products). Thoroughly research any product advertised on the site before you decide to download and install it.
Hornblower409 10,455 Reputation points

2026-07-02T13:50:04.4533333+00:00

Just to add an image to the instructions from Chloe.

When you run the iCloud for Windows program you should see something like this. The "Calendars and Contacts Open in Outlook" toggle must be "On".
Hornblower409 10,455 Reputation points

2026-07-02T14:31:46.74+00:00

Bonnie Lipner said

I used to have a round arrow to synch mail - and when that was grey it meant the "Add-in" needed to be reset..

You are talking about this? When you are looking at your iCloud email account and click the "iCloud" menu tab.

And now you don't have an iCloud Mail folder? Or you have the folder but there is no Refresh button?