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  • MS 365 Outlook and Apple Mail/Calendar Connectivity

    Posted by Bill Miller on January 26, 2025 at 1:51 pm

    I am looking for to help (or a resource to help) with making MS365 and Apple iPhone Email and Calendar (specifically calendar) to work together properly, e.g. accept calendar invite. Apple will not help with MS products and MS support leaves a lot to be desired. I use Outlook and MS365 on my iPhone and PC Laptop. My wife uses an iPhone and an iPad.

    I believe this is a simpler problem that it seems to be because of the lack of coordination/cooperation between MS and Apple.

    Any help would be greatly appreciated.

    Bill M.

    Bill Miller replied 2 weeks ago 2 Members · 8 Replies
  • 8 Replies
  • Bill Miller

    Member
    January 26, 2025 at 1:53 pm

    I meant to add that my wife uses Apple email and Calendar.

    • dfhjr

      Member
      January 26, 2025 at 4:01 pm

      I have MS Office 365 and run the downloaded Office programs on my W11 PC. My wife and I also have iPhones and iPads. Each of us maintains our own Apple calendar. Each calendar resides on iCloud. She shares her calendar with me, and I share my calendar with her. We each can see both calendars on all of our Apple devices.

      In MS Outlook, there is an Outlook add-in called “iCloud Outlook add-in” accessible via Outlook >> File (menu) >> Options (left side menu) >> Add-ins (left menu) >> Manage (bottom center panel) COMM Add-ins (pulldown list) >> Go. Make sure the iCloud Outlook add-in checkbox is checked and select OK. This should enable an iCloud menu item in Outlook (It may be necessary to restart Outlook.) If you don’t have the iCloud program on your PC, you will need to install it (https://support.apple.com/en-us/103232) and log in to the iCloud program with your AppleID. Once you log in to the iCloud program, it should restart and run in the background when you log in to your PC. I’ve found a PC restart after the installs often helps resolve connection issues. Sometimes Apple and MS don’t play well together. If you do a PC BIOS update, you will likely be prompted to log in to your iCloud program again.

      You can use the Outlook iCloud menu item to refresh your access to your Apple Calendars for Outlook. To see the calendars, open Calendar and look for the list of accessible calendars below the months displayed in the left hand column. If you scroll down through those calendars, you should see iCloud and the iCloud Calendars beneath you can access. Click the checkbox of a calendar you want to see and the contents of that calendar should appear with the appointments in that calendar.

      We maintain all of our appointments in our Apple calendars, adding / changing / deleting appointments on the Apple devices, and viewing them in Outlook. I have had problems going the other direction.

      This set up has worked for me for a number of years, many patch levels and BIOS changes. There are a number of steps, but they are doable.

      Good luck,

      don

    • Bill Miller

      Member
      January 27, 2025 at 11:52 am

      Not sure you got my reply to your response that came into my email inbox. So here it is again…

      Don (dfhjr)

      Thank you for helping with this issue. You have given me more relevant and actionable information with this response than the two trips to the Genius Bar at the Apple store and a couple of hours (at least) on the phone with Microsoft support. And it looks like you’re a bike rider too!

      Thanks!

      Bill Miller

    • Bill Miller

      Member
      January 27, 2025 at 1:26 pm

      Don,

      Couple of questions, if you don’t mind. Does your wife use Outlook as well or does she just use the Apple suite? Did you ever try just sending invites from your wife’s calendar to your Outlook calendar and vice versa? This seems to work but involves and extra step since it goes to email and has to be accepted before it appears on her Apple calendar.

      My wife has an old MS “.msn.com” account as well as her Apple account so I think this adds a level of complexity that is unnecessary. I think it is past the time to migrate away from that account and just use the Apple account & suite for her.

      Thanks again for your help!

      Bill

    • dfhjr

      Member
      January 29, 2025 at 1:09 pm

      Bill,

      It’s been my experience that MS and Apple are often at odds, and “what used to work” either goes away or changes as new patches from both vendors occur over time.

      My wife uses her Apple products exclusively for any calendar related activities. I don’t think she even views her calendars on her PC. She does email across both Apple email (not the Outlook app for Apple) and PC based Outlook (she is logged into her PC with her MS Outlook account, but has multiple email addresses across multiple services that she monitors). Most of the email works pretty seamlessly. All of her calendar activities are done on Apple products with Apple calendars. She has her own calendar which she shares with me via Apple

      I maintain my own and a number of other Apple calendars (tentative activities, garbage collection schedules, hobby related special events, …) which I share with my wife. All calendar entries and modifications for both of us are made to the appropriate Apple calendar. I ignore my MS Outlook, Google gmail and other service calendars; they don’t exist as far as I’m concerned. We share some of the calendars with our adult children so they can see things like our travel plans, etc. They use Apple products.

      I access these Apple calendars on my PC by the set up process I described previously. The only calendar activities I do on my PC are decorating entries with MS categories or availability markings. If I’m working on my PC and discover I need to modify a calendar event, I turn to my Apple device and do it there.

      For email, we basically ignore our Apple and MS email addresses. We depend on other services. We ignore the email web interfaces and download them to our devices via an email client.

      After you have your calendars running across platforms and if you use Outlook Tasks for your reminders, they can be done with some limitations across platforms.

      Good luck,

      don

    • Bill Miller

      Member
      January 31, 2025 at 9:19 pm

      Don,

      This information is very helpful. I have become very comfortable with with the MS suite of products over the years, and particularly the integration of Outlook and the To-Do applications. I’m sure I can get to a happy place now with your suggestions.

      Thanks again,

      Bill Miller

  • dfhjr

    Member
    January 29, 2025 at 1:23 pm

    Bill,

    I forgot to mention:

    Yes, I ride bike though not long distances. Most rides are 10 – 15
    miles round trip from my home location on hard surfaces. I ride a
    Specialized Sirrus during the summer, and am currently riding a
    DiamondBack Wildwood. I’m in my early 70s, riding with some replacement
    parts (hip, knee). As I tell others, I belong to the Half Fast riders
    club.

    Not slow, not fast; only half fast,

    don

    • Bill Miller

      Member
      January 31, 2025 at 9:30 pm

      Glad to hear you are still riding. I did a lot of road rides in San Diego and Baja. We live in SD. I did the Senior Olympics in Pasadena when I was 74 and had a great time, even though I did not qualify for the Nationals in Utah. After my hip replacement in ’21 (Pickle Ball) I sold my Specialized Roubaix. It was a sad day.

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