synching between Outlook 2024, and my iphone for months

Hi Bonnie Lipner,

Thank you for the update. I'm glad to hear that you have found a temporary workaround by using Send/Receive, although the process may take a bit longer.

If you encounter any further issues or have additional questions regarding this matter, please let me know. I’ll be happy to assist you further.

Please look back on the post regarding the use of the Refresh button. My system has no such button anymore and I have been unable to find a way to add it to my Tool Bar.

Regarding my orginal issue of not being able to synch my Outlook calendar, I cloud calendar and Iphone this issue contines to exist for the past 6+ months. I have spent days on the phone with chats, encountered Quick Assist support that made things worse, where I needed to recover contacts and and other files myself, after they disconnected leaving me a mess, and have been unable to get the Microsoft Add-in used to connect this to work. I am not a first time user.. I have had Outlook synching for decades and and this is the first time I have been unable to get to a higher level of Outlook support to fix this. If you are aware of a means to contact a high level of Outlook support, purchase a contact, or attain a solution please advise. SO MANY QUICK SUPPORT PEOPLE HAVE MESSED WITH THIS AND THEN DISCONNECTED AFTER THEY LEAVE ME A MESS thaat my PC is now a mess.. Duplicate folders, added new calendars, and left a ton of items pinned in Explorer???

Hi Bonnie Lipner,

I'm sorry to hear that you've been dealing with this issue for more than six months. After spending so much time troubleshooting, contacting support, and encountering additional problems along the way, I completely understand how frustrating this situation must be.

Please note that this is a user-to-user support forum. Moderators, contributors, and external Microsoft employees cannot intervene in Microsoft product features, access back-end systems, or escalate cases directly. Our role is limited to providing technical guidance based on the information available.

Due to the nature and long-running duration of the synchronization issue between Outlook, iCloud, and iPhone, contacting Microsoft Support directly is the only official channel available for account-specific troubleshooting and investigation.

• Go to Contact Us: https://support.microsoft.com/en-us/contactus
• Click Show expanded list of products
• Select Outlook > Get Home support
• Type Outlook live chat in the search box, then select Get Help > Contact Support
• If you can’t sign in to the affected account, sign in with a different Microsoft account to access support options
• Under Products & Services, select Other Products > Outlook, then choose Chat with a support agent via web browser

I sincerely regret the inconvenience this issue has caused. Hopefully, Microsoft Support can review your case in greater depth and identify why synchronization between Outlook, iCloud, and your iPhone continues to fail.

Thanks for your response. Your instructions are exactly what I have been doing. Then I give them the Reference Numbers (ALL OF THEM) and wait while they read. The classic next move is asking the same questions, doing the same things, and getting the same results.. At times they give up and disconnect.. that's disturbing. I have been a loyal Microsoft user forever.. with my business I was a Microsoft Parnter - till I retired.. I love the concept of this question/Answer forum.. but I'm getting no where..

I guess I'll try again when I get another block of available time..

THANKS

Bonnie said

I love the concept of this question/Answer forum.. but I'm getting no where

I am willing to keep working on your problems via this forum if you wish. But because I can't see your screen or take control of your PC to make immediate changes, it is going to be a slow and tedious process.

If you wish to continue:

The first step is to narrow down our focus to one issue at a time. Can you please identify the single issue that is causing you the most pain, or that you think might be a root cause of multiple other problems?

Hi Bonnie Lipner,

Thank you for the update. I completely understand your frustration, especially after already working through these steps and providing multiple case reference numbers.

Unfortunately, as this is a public user-to-user forum, we don't have access to support cases or the ability to escalate them. At this point, Microsoft Support remains the only channel that can review your account-specific investigation history.

I sincerely hope your next contact with Support leads to meaningful progress. If you receive any updates, please feel free to share them here.

Hornblower409

Thank you for your help.

For years I used an  Outlook for everything.  My Calendar (different verisons based on time) would synch with my iphone calendar, and  icloud.  A number of months ago while using  Office 2019   
I lost my synching between my calendars.  At first I didn't realize it, but when I had ememrgancy open heart surgery and needed access in different places I found out.  I contacted Microsoft Support, we had chats, and Quick Assess calls.. After one quick access contact the support person said 2019 is no longer supported, and she just disconnected.  To shorten the story I got Office 2024 PRo.  Since then I have been unable to get anyone to make the synch work.  I thought it was maybe the Add-in..... but each support person had their own thoughts.  As of now I have no synching. 

If I add an event on my phone it goes to the cloud but not Outlook.

If I add an event on the icloud calendar it goes to the iphone but not outlook calendar.

If I add an event from Outlook calendar is only on that calendar.

I have disabled the add-in.. shut down -- enabled it agin.. no change.  I'm afraid to delete it since I have no idea where to get it back.. and I'm not sure that's the problem.

Synching just is not working.  ANY HELP AT THIS POINT IS GREATLY APPRECAITED.

Bonnie,

To sync your Outlook 2024 Calendar with your iCloud account requires "iCloud for Windows" to be correctly installed on your PC. Let's start there.

• Go to the Microsoft Store https://apps.microsoft.com/detail/9pktq5699m62?hl
• Click [Download]
• 
• This should download the "iCloud Installer.exe" file
• Click the Open button in the downloads dropdown.
• 
• This should show the program as being installed or updated. Either way it should then show you an [Open] button. Click it.
• 
• This should open the iCloud for Windows main screen. And there should be an "iCloud" icon on your desktop.
• 
• 

Stop there. Come back here and advise if you had any problems doing this part.

Sorry it took so long.. I had actually done this quite awhile back, but for some reason did not reply correctly.

I have that on my screen, all items are "on" and my "backups" are using 3.55 GB with 1.44 Gb free. I have NO idea why that "Backups is so large.

Bonnie said

my iCloud "backups" are using 3.55 GB with 1.44 Gb free. I have NO idea why that "Backups is so large

I am sorry, but that's not a question I can answer. Since it's about your iCloud storage usage, all I can suggest is that you post a new question about that specific problem on the Apple iCloud Support Forum.

[External Non-Microsoft Site] https://discussions.apple.com/community/icloud

Sorry I got sidetracked.. with the prior response. I did what you asked and was responding to "Stop there. Come back here and advise if you had any problems doing this part." No problem that I can see.

Bonnie,

If you have the iCloud for Windows software installed correctly. The next steps:

1 -- Open iCloud for Windows by double-clicking the icon on your Desktop, or use the Windows Start menu and look for iCloud

2 -- On the iCloud main screen, click [Account Details]

3 -- On the Account Details dialog, click [Sign-In], or [Sign Out] if you are currently signed in. (You MUST go thru the Account Sign-In process even if you are currently signed in).

4 -- Complete your Apple iCloud sign-in using the normal Apple process for your account. The exact steps will depend on how you authenticate your Apple account (password, code sent to an Apple Device, text code to your phone, etc._

5 -- After your Apple Sign-In is complete, you should see a series of screens asking you which iCloud features you want to enable. e.g.

6 -- Click [Not Now] for all of them except the last one "Sync Calendars and Contacts". On that one click "Sync Calendars and Contacts".

7 -- And then [Finish Setup]

8 -- You should see a series of "Outlook Setup for iCloud" progress screens and then a "Setup is complete" screen. Click [Done].

9 -- You should be back on the iCloud for Windows main screen with the "Calendar and Contacts" switch "On" and the text "Updated just now" below the Calendar icon.

Stop there and advise of anything that didn't go exactly as I described.

I read thru all your steps... before I started and they make sense.. so I started following them.. When I got to the sign out of icloud I got a message that concerns me alot. The first popup regarded images.. and I really had no images to worry about so I said ok.. and moved on.. then it went to "all files" and that's where I stopped. I don't know how to make a back-up of these other files and I can't afford to loose what's on my icloud drive, Passwords and especcially my calendar... this leads me to beleive if I continue each popup will delete things from my PC.. Will the information in each catagory just mentioned be there to re-synch or download back for me to access.?

I really apprecaite all your help!!

Bonnie,

I didn't realize that you were using all of the iCloud features, including iCloud Drive. For sure, if it's something you have been using in the past, when presented with that choice during Sign-In, select it.

Just to be sure I understand this.. It deletes the items JUST FROM MY PC.. and I can gt them back during Step 9 as listed above?

Bonnie said

It deletes the items JUST FROM MY PC

Yes. But as I said before, if you were already using iCloud Drive then continue to use it. Same for all of the services on the 5 Screens that ask you what iCloud services you want to use. Say "Yes" or "Install" to them all. (Whatever the other choice is besides "Not Now").

[Cancel] on the Turn Off iCloud Drive and start all over again with the iCloud Sign-Out/Sign-In.

It did not say Updated just now under "calendars and contacts".. but I feel like it did update... Also- I put a test event in my calendar on **my iphone** - It went to the cloud calendar, but did not appear in either of my calendars in outlook.  (The 2 calendars are named Calendar (from Gmail)  & Calendar -  icloud.  What am I missing?

Bonnie said

It did not say Updated just now under "calendars and contacts"

Then something probably went wrong.

I put a test event in my calendar on my iphone ... did not appear in either of my calendars in outlook

Any changes in your iCloud Calendar should show up in Outlook under your iCloud folder. e.g. I see:

Let's try the Sign-Out/Sign-In again.

But this time for step 6, you click the button opposite of "Not Now" for all 5 screens. And watch closely when it gets to Step 8, do you see the "Setup is complete" screen?

I said “not know” to each of the 5 selections – and the the next screen was “Finish Setup”.

After that it brought me back to the screen

“Apps Using Cloud” and everything is “OFF”

It never said “setup is complete”. And as you can tell from the image it says “Not Set Up”.

Should
I manually turn on each of the 5 items?

I'll wait to hear from you.. THANKS SO MUCH

Bonnie said

I said “not [now]” to each of the 5 selections – and the the next screen was “Finish Setup”.

Based on your screen shot it looked like you had all five options enabled. So my suggestion was to do the Sign-Out/Sign-In from the beginning and turn them all ON/Enabled (whatever other choice there is besides "No Now").

Should I manually turn on each of the 5 items?

No. We need you to do a full Sign-Out/Sign-In from Step 1 and enable all five options. That is the only way I know of to force iCloud to do a full re-install of the needed components.

Here’s where I stand..

·       I signed out of icloud..

·       I closed all my programs and did a shut down.

·       I went back in thru “Start” and opened Icloud and ran the set up.

·       The set up finished and I got a message “Setup finished” It didn’t say anything went wrong as it went thru the steps.

·       I then restarted my PC.. and entered a event in my phone calendar as a test labeled “Test from Phone 7-30 10:00AM”.

·       I checked the cloud -- That event shows up in the cloud..

·       I opened Outlook and waited for the send-Receive the finish - but the event is not in my Outlook. I now have an addditional Calendar - "Outlook Data File" that has no entries? and two that are labled "Icloud" .

I’ve attached a few images.. I hope this helps since explaining is is now an issue for me since I really don't know the proper names for somethings.

Now what??????

Bonnie said

I now have an addditional Calendar - "Outlook Data File" that has no entries?

Yellow. That is from a dummy PST file that is required by iCloud. Just ignore it.

If you want the gory details see: "Cannot Start Outlook..." Error in
[External Non-Microsoft Site] https://www.slipstick.com/problems/outlook-and-icloud-default-data-files/

and two that are labled "Icloud"

Green. It looks like it has been renamed. Is it just a GMail calendar?

Blue. What account is it attached to? Seems to be a duplicate of Green?

Pink. Looks like the iCloud and I see events. What did you add that didn't come over?

Contacts - Also check you Contacts/People. Do you have an iCloud Contacts folder?

Bonnie

Need to get your Navigation Pane (usually a bar on the left) into Folders View so we can see the actual data files. This gets tricky because Microsoft has changed how the Nav Pane works.

1A -- If you see a Folders icon in the bottom left corner of your window, click it. If you see a three dots menu in the bottom left corner of your window, click it and choose Folders.

1B -- If you have the "Apps Bar" on the left side of your window and there is a Folders icon, click it. If you have the "Apps Bar" but there is no Folders icon, click on the "More Apps" icon at the bottom of the bar and choose "Folders".

2 -- Once you have your Nav Pane in Folders View you should see something like:

1 = The Dummy PST required for iCloud

2 = Your iCloud email top folder

3 = Your iCloud sync top folder (Calendar and Contacts)

Is this even close to what you see?

Hope this is what you need.. For some reason after one of the Microsoft Techs was helping me-- the folders got messed up and I didn't fix them when we loaded an older backup. I have mostly been concerned with the synching issue.

Bonnie

It doesn't look like you have the Navigation Pane in Folders View. Please do:

1 -- Click on the "More Apps" icon. Right-click on the Folders icon and choose "Pin"

2 -- Switch to the Folders View in the Nav pane. Collapse all the top level folders. Take a screen shot. (Redact some part of any full email addresses). Should look something like this:

3 -- To go back to your normal Nav pane, click the Mail (Envelope) icon in the Apps Bar.

I hope this is what you are looking for?? -- THANKS AGAIN..

Bonnie,

Yes that is exactly what I wanted to see.

Expand the iCloud top level folder. You should see:

Click on "Contacts". Do you see your iCloud (only) Contacts?

Here's what I have.. Each time a tech person worked on my issue it seemed I got more groups.. and I didn't want to clean it up until I had my problem solved. 2 images attached.

(As a side note one tech pinned 23 folders in File Explorer - I know I can unpin them once this is all working.)

Bonnie said

Here's what I have

So it looks like your iCloud Contacts are in Outlook. Next test is to see if they are syncing with your iCloud.

1 -- Open the iCloud Contacts Web interface at https://www.icloud.com/contacts/

2 -- Pick a Contact and Edit

3 -- Add a Home Phone

4 -- Enter a Home Phone number and Save

5 -- Open the iCloud for Windows program. Check the "Calendar and Contacts" Updated field near the bottom of the page.

If it is blank or says "Updated just now" you are OK. Anything else (e.g. "Updated today at H:MM PM") means the sync has stalled.

6 -- In Outlook, switch the Nav Pane to Folders View, expand the iCloud top level folder, and select Contacts. In the Contacts list Select the Contact that you modified in iCloud and check that they now have a Home Phone.

Assuming I followed your direction correctly-- the updated phone number did not appear in the "icloud contacts" List.  (I waited for the send receive to finish and checked then)

Also.. in step 5 I did not see any indication that mentioned "updated now".. image below. So I guess it's not synching? I did tghe process twice on two differnt contacts..

Bonnie said

I waited for the send receive to finish and checked then

iCloud Sync is not part of the normal Outlook Send/Receive. It runs independently of Outlook. Usually should sync within a minute or two of any changes in your iCloud Data.

I did not see any indication that mentioned "updated now"..

It's kind of flaky. Sometimes (not always) you will see either "Updated just now" or "Updated NN minutes ago". But not always. I don't know why.

the updated phone number did not appear in the "icloud contacts" List ... So I guess it's not synching?

Unfortunately, no. It's not syncing. Here we go again.

• Close Outlook
• Open iCloud for Windows.
• Expand the "Calendars and Contacts" section.
• 
• Turn it "Off" and [Done]
• 
• Reboot your PC
• Open iCloud for Windows.
• Expand the "Calendars and Contacts" section.
• Turn it "On" and [Done]
• Do you see the "Setup is complete" dialog?
• 
• Open Outlook and Check the iCloud Contact where you added the Home Phone.

I tried this twice- once using a restart and once with a shut down.. no luck. It just didn't show up. Which got me to thinking of the mess that has been ceated during the number of Quick Assist sessions with Microsoft Tech. I started to look at some things that I
can't get straight in my mind, and maybe the system just is confused as I am?

Northing matches.. Attached are a few print screens with notes.. maybe they will stir something you can figure out. #1 image is a list of folders when I opened Outlook from the Task Bar on my Pc. Green is empty - Yellow has a few items.. the as you can tell from the numbers the unmarked folders have a good number of items. #2 A list of folders from my iphone contacts. the numbers on folders don't match the prior list #3 the contacts folder from iclous witj 676 items.

I'm willing to delete all the small folders that are empty or have just a few items.. in fact the 955 items in All Contacts on my phone have duplicates.

Bonnie said

maybe the system just is confused as I am?

Possible. I think maybe it's time for a different approach. I am going to start a new Answer on this Quesiton titled "iCloud Only Profile". Please pick up our conversation there.

 Thank you for your help. I was doing ok with the other supporting person, but what he was asking me to do I just didn't understand. I hope my answers are clear.. and my images help to explain myself. I REALLY have depended on Outlook forever, and would love to get this handled.. so
I can clean up all the mess that has been created.

ANSWERS

Are you using Classic Outlook for Windows or New Outlook__?   “Classic” When I go to the start – my list of programs says classic outlook.__

Is the calendar you want to sync an iCloud calendar, Outlook.com calendar, or Microsoft Exchange/Work calendar?  I believe it to be the icloud calendar – prior to loosing the synch I had one calendar that had all my entries/events on it . Now when I click the calendar in the upper left corner in outlook I get a view with 3 calendars.  See image

·       Outlook Data File – empty

·       Calendar (from Gmail)

·       Calendar - icloud

Is iCloud for Windows installed on the PC and signed in with the same Apple ID as the iPhone? Yes.  And I have reinstall I cloud for Windows because a previous support person said to..

In iCloud for Windows, is Contacts and Calendars turned on and applied? Marked as on.. not sure what applied means.. see image I sent.

In Outlook, do you see an iCloud Calendar folder? Yes – see image.

NOTES

Contacts

·       I added a new contact via my phone and it does appear on my icloud list when I look at contacts thru the cloud on my pc.

·       If I add a new contact using Outlook, and try to place it into my all “contact-I cloud” folder it does not show on my cloud when I look using my pc.

Calendar

·       If I enter an event in outlook calendar names calendar – icloud it does not show up on my phone.

Images below

Bonnie,

Thank you for all the details. But for now, let's just work on iCloud Contacts.

1 -- From your "Contacts as viewed in Outlook vs Contacts as viewed in iCloud" picture.

Your pics of Outlook are with the Outlook Navigation Pane in the "People View". In that view all of your iCloud contacts get mushed together under a single group. (Or in your case two, since you have two separate "Contacts iCloud" groups. Which I can't explain).

To get a true picture of what's in your iCloud Contacts in Outlook you need to switch your Navigation pane to "Folders" View.

In the far left "Apps Bar", click on the Folders icon.

This should get you the "raw" view of your iCloud Contacts Folders. e.g. For me it's:

Is that a closer match to what you see when you use a browser to open you iCloud Contacts?

Are the folder missing in Outlook ones that were added to iCloud after your sync stopped working?

I'm really interested in getting my calendar to synch.. I'm assuming the calendar and contacts are attached somehow.

I'm attaching a list of what is in what place.. hope it helps. I really don't care about the misc folders like Dr., Family Fundrasing.. I alsways assumed the names where all in "one master folder" .. that's all I really need now.

Hope this helps.
I have no idea when the folders dropped off from one list or another.

@Bonnie Lipner said

I'm assuming the calendar and contacts are attached somehow.

Yes. Usually they either both work, or both are broken. Contacts are usually easier to test with. That's why I ask to concentrate on Contacts first.

I really don't care about the misc folders ... I alsways assumed the names where all in "one master folder" .. that's all I really need now

I understand. But to debug I need to see the actual, separate Folders under your iCloud account.

As previously described - In Outlook, switch your Navigation Pane to "Folders View", expand the iCloud account and screen shot what you see.

Thought I had sent this to you.. I had to google how to get that view.. THANKS

I received a response to yesterdays request and screenshot..time stamped this morning at 12:17Am.. but when I open it this AM I had a 404 Error. I tried again just now - same thing..

By the way it had this screenshot

I received a response to yesterdays request and screenshot..time stamped this morning at 12:17Am.. but when I open it this AM I had a 404 Error.

If you are saying that the link in the notification e-mail is generating an error, that could be the result of your message being edited in the forum (converted from an Answer to a Comment, for example). You can always click the thread title to get to the correct thread from the notification.

I tried to go back to the thread, but my comment was not there. Hence the comment I posted..
If there soemthing else I can do?

Thanks for your help.