Best family calendar service for Outlook 2013/2010, iOS, Android and web?

As a starting point, I will now be the first to describe the setup that we currently use in my family.

Our current family calendar setup is a mix of outlook.com and Exchange Online.

The youth use outlook.com; the parents use Exchange Online.  The total price is $8 per month.

The youth is using outlook.com

How to share own calendar:

The personal calendar is (privately) published to the internet (Calendar > Share > Get a link > ICS). The link is given to the family, it looks something like this: webcals://sharing.calendar.live.com/........ics.

How to view other calendars:

Get the private ICS links from the other family members and subscribe to their calendars. Tip: If you receive an error then try replacing “webcals:” with “https:” in the link.

Benefits:

• The above is enough to provide a consolidated calendar with both own and other family member’s appointments on web (outlook.com), Outlook 2013 University, iOS and Android.
• The youth can respond to meeting invitations from the parents.

Drawbacks and limitations:

• The subscribed calendars from outlook.com and office365.com only refresh every 2-3 days. This is by design and Microsoft explicitly writes: “… this update can take more than 24 hours”.

• Outlook 2010 cannot be used at all; the hotmail connector crashes.

• Outlook 2013 cannot be used to manage contacts.

• The youth cannot arrange meetings.

• Androids can only be used for emails, no calendar updates or acceptance of calendar invitations. This may be a specific Android issue.

The parents are using Exchange Online

How to share own personal calendar:

The personal calendar is (privately) published to the internet by making a link to share with everyone outside the organisation. The link is given to the family. I may also have changed the settings to share calendars with external users.

The calendar is also shared directly (within the organization) with the other parent.

How to view other calendars:

Get the private ICS links from all the other family members and add their calendars to your calendar view (step 4). These calendars will then be visible on web, Outlook 2010/2013, iOS and Android.

Also add the calendar shared “within the organization” (step 3) by the other parent.

Benefits

• The above is enough to provide a consolidated calendar with both business, personal and family member’s appointments on web (office365.com), Outlook 2010/2013 and iOS.

• Outlook 2010/2013 and iOS can be used manage contacts and arrange meetings with the rest of the family.

• The calendars shared “within the organization” are always fully up-to-date and can be seen on web and in Outlook 2010/2013. (iOS only supports the subscribed ICS calendar)

• I have experienced Exchange Online to have much better quality, robustness, web speed and support compared to outlook.com. Roughly 5 times better on all parameters :)

• Possibility for a one month free trial of Enterprise E3 including Exchange Online. Highly recommended! Be careful when choosing the tenant name, it cannot be reused or changed!!

Drawbacks and limitations:

• The subscribed calendars from both outlook.com and office365.com refresh every 2-3 hours.
  (This can also be seen as a major benefit compared to the 2-3 days in outlook.com)
• Exchange Online has more features than outlook.com, so setup takes more skills and effort.
• Exchange online has a few limitations compared to outlook.com (e.g. only one outgoing email address per user)
• The price of Exchange Online is $4 per month per user. This is $96 a year just for the parents in our little family.

Exchange Online on own domain

If both the youth and the parents use the same personal domain (myfamilyname.com) then Exchange needs to be setup to relay emails from the parents to the (forwarding) mail service of the youth. The trick is to

1. setup the personal domain for “internal relay” (Office 365 Portal > ADMIN > Exchange > mail flow > accepted domains > myfamilyname.com)

2. create an outgoing connector to the mail server used by the personal domain (Office 365 Portal > ADMIN > Exchange > mail flow > connectors)

The above setup also allows additional mailboxes hosted directly at the mail servers of the personal domain.

iOS bonus information

I like the iOS App: “Calendars by Readdle”. It reads the content already synchronized to the native iOS calendar and then allows me to have a very nice week/month overview - very much look like the outlook calendars.

Other considerations

I have considered moving the entire family to Exchange Online, but that would really be killing mosquitos with cannons. Exchange Online is designed and priced for business users with high requirements like the financially backed uptime of minimum 99.9%. We can easily live with less and therefore find it superfluous to add another $192 on top of the $79 for a 4 year Office 365 University subscription. Especially because we do not like to financially reward Microsoft for the exceptionally low quality of the already included complementary service (outlook.com).

My future setup

Surely, the current setups is no a long-term solution; we just use it to keep the family coordinated while I search for better alternatives. I am painfully aware that the personal use of the Microsoft Office suite is the root cause driving us into the outlook.com troubles, so Microsoft Office is also included in my search for alternatives. This situation then opens up the search to include other operating systems. I guess you by now understand why I paid a bit to gain sufficient time to investigate and test my next move.

Kind regards, Ole :)

PS: I most likely missed some technical details above, so please feel free to ask if something appears to be wrong or missing – or just needs some additional explanation.

Unfortunately, this is impossible because outlook.com has far too many critical errors and stability issues in the core functionality. This has been the situation for years (at least since 2013), and there are currently no indications that it will change significantly in the coming years.

Hi Ole, thanks for your clear write-up of your problems with Outlook.com's Contacts and Calendar.

I will study the setup-up you are using in your family in the coming days.

In the meantime, I would like to contribute to the discussion by pointing out the Calendar synchronization issues I and many others are experiencing with Outlook.com.

I have reported them in this thread:

• Is calendar synchronization between Office 2013 and Outlook.com capped by spam or bandwidth limits?

Regards,

Paul

My main question would be:

• If fixing the Outlook.com core platform would take a long time, then why can Microsoft not quickly release a private-use version of their Office 365 Business Essentials service, which would provide access to 5 Microsoft Exchange Online accounts (mail, contacts, calendar), and using the Outlook.com domain name (or a new name created for this family service)?
• Such extension need not be free, I believe many would gladly pay an fairly priced fee for a reliable and ad-free service, providing mail, contacts and calendar service for the entire family.
• It would be a great alternative to Google's or Apple's platform.

What do you think about this, Ole?

A large organization like Microsoft will also take a long time to define and release a new product like the one you propose. I doubt it can be done in 6 months, perhaps 1 year with high management commitment.

Therefore, the only quick fix possible would be to somehow refund the costs associated with using the existing Exchange Online until the issue is fixed. This would demonstrate a high commitment to customer satisfaction and create internal pressure to quickly fix the issue. I have never seen anything like that from Microsoft, and will be surprised if it happens. Microsoft simply does not yet feel the same fierce competition as seen for cars, hotels, airlines, etc.

I currently pay, but I doubt many would be ready to pay for a basic family calendar; similar services are well functioning and completely free if you shop elsewhere (e.g. Apple). The only drawback is that their services do not integrate so well with Outlook 2013, so to me the payment question really boils down to: How much are you prepared to pay extra to use Outlook 2013 for your family calendar – on top of the already paid Office licenses/leases?

I doubt many would be ready to pay for a basic family calendar; similar services are well functioning and completely free if you shop elsewhere (e.g. Apple).

The only drawback is that their services do not integrate so well with Outlook 2013, so to me the payment question really boils down to: How much are you prepared to pay extra to use Outlook 2013 for your family calendar – on top of the already paid Office licenses/leases?

What puzzles me about this situation?

• That the IT press has not reported on the fundamental issues with Outlook.com's contacts and calendar cloud services.
• That Microsoft has let a truly fundamental problem with a core cloud service linger and go unresolved for such a very long time now already.
• That Microsoft is unaware of, or willing to take, the risk that many frustrated home users will abandon its platform and move to Google or Apple.

Alternative solutions?

1. Continue to use Outlook 2013, and replace Outlook.com by Google's cloud platform. In that case we need a "middleware" to sync Google Contacts and Google Calendar. There is a free open source tool available, Go Contact Sync Mod, but I have experienced issues with it. Some people may also not like the fact that Google will build a "marketing profile" based on your personal data, and will therefore reject Google as an alternative to Microsoft.
2. Continue to use Outlook 2013, and replace Outlook.com by Apple's cloud platform. I have no personal experience with this, but I have seen reports that Apple's platform is not as full-featured as Google's and Microsoft's, and that compatibility with non-Apple devices is not as smooth as one would want. To be confirmed...
3. Continue to use Outlook 2013, and pay for Microsoft Office 365 Business Essentials for use as a mail, contacts and calendar repository. This seems to be a robust solution, but it costs $4 per month, per user. It's too expensive for family use.
4. Abandon Outlook 2013 and start using the Google or Apple cloud platform with a web browser client. However, using a web browser as a front-end may have some disadvantages (for example, offline use is not as smooth).
5. Abandon Outlook 2013 and start using an alternative desktop client software. On Windows pc's, there are not many alternatives available to replace Outlook 2013 for both mail, contacts and calendar functions. I have started testing eM Client, which appears promising at first sight. (Note that its free version is limited to 2 mail accounts per user, e.g. your personal and your business account). Unlike Outlook 2013, eM Client has built-in synchronization support for Google's platform (and others, including Outlook.com, iCloud, Exchange), so a combination of eM Client and Gmail.com could be a alternative to the combination of Outlook 2013 and Outlook.com. See also this review of eM Client.

What puzzles me about this situation?

• That the IT press has not reported on the fundamental issues with Outlook.com's contacts and calendar cloud services.
• That Microsoft has let a truly fundamental problem with a core cloud service linger and go unresolved for such a very long time now already.
• That Microsoft is unaware of, or willing to take, the risk that many frustrated home users will abandon its platform and move to Google or Apple.

Hi Paul,

I have had the exact same thoughts. They are easiest commented from the bottom. I find that Microsoft’s behavior is due to one of these two scenarios:

Focus on other more important and urgent matters
Big businesses did not embrace Win8/Outlook2013, but stayed on Win7/outlook2010. Businesses want useful and well-functioning products that increase productivity, not a new fancy design with animations – especially not when the new design comes with additional learning and a lower quality product (“icing the half-baked cake”). Microsoft has realized this and are now concentrating all their best resources on business features in Win10/Outlook2016, and we see the consequences in personal services like outlook.com.

Microsoft being completely complacent and therefore not realizing the situation
This is the impression we get when seeing all the auto responses from Microsoft and MVP’s in this forum. Nobody thinks, that perhaps this is a programming error in our software, everybody starts out be assuming that issues are due to hardware, setup or user errors. This is the scenario supported by prominent people like John P. Kotter: https://hbr.org/2013/11/accelerating-change-at-microsoft

IT Press

We both know that it takes quite some time to collect and verify the information to build a forum supported list of critical issues. The IT press does not have the resources to do this. It is much easier to make a quick shallow review of the new Windows 10 preview, and it probably also generates more hits and clicks on the ads.

In addition, the issues are not really news considering the above well-known scenarios. Then it is just small ripples on the surface… (no pun intended ;-)

Anyway, now I feel we are getting a bit too much off-topic (finding the best calendar service), so let us leave room for other forum members to add real life experiences with other outlook.com alternatives.

Alternatives

Thanks for your list of alternatives, please let me know what you choose if you replace outlook.com.

Kind regards, Ole :)

Thanks for your list of alternatives, please let me know what you choose if you replace outlook.com.

• I purchased a 2-user 1-year license for Microsoft Exchange Online Plan 1 (3.1 euro per user per month). This seems to be a robust solution (in my currently limited experience, and from what I heard from you and others). When this first year expires, I will evaluate the situation again.
• Also, we continue to use Outlook 2013 (on Windows) and Google's Gmail, Calendar and Contacts apps (on Android) as clients, because we have grown so accustomed to them over the years, and because they have a feature set that we did not find in alternatives.

I will continue to monitor this thread for future inspiration.

Unfortunately, this is impossible because outlook.com has far too many critical errors and stability issues in the core functionality. This has been the situation for years (at least since 2013), and there are currently no indications that it will change significantly in the coming years.

Diane just pointed my attention to this Verge article:

Microsoft's Outlook.com will be powered by Office 365

The article appears to be “officially leaked” when a named Microsoft general manager starts speculating in an interview, so now there is at least one unofficial indication that the situation will change in the coming years.

I sure hope Microsoft will completely replace the current outlook.com server architecture by the more robust architecture powering Exchange Online. Just wondering how it will be limited to prevent all businesses from using it. Tip: Reserve the right to severely throttle the (free) personal service in peak business hours to free resources for (paying) business class users.

Diane is now trying to get an official confirmation with expected swap dates etc.

Ole :)

Microsoft's Outlook.com will be powered by Office 365

Ole, if confirmed, that would be most excellent news!

Paul