Problems creating Skype meeting in Group Calendar on Web Interface

[Brett Hinton]

I find that in two different Office 365 tenants my organization is unable to create an event and add a skype meeting to that event on the Office 365 group calendar via the web interface (outlook.office.com). We seem to be able to create the event with an attached Skype for Business meeting in the Outlook 2016 client but on the web it fails to create.

Has anyone else run into a similar issue? I have had a support incident open with Office 365 support for about a week and a half now and they don't seem to be seeing the problem in their test labs or able to run down the issue.

[#2]

I have not seen this kind of issue on the tenants I manage

[#3]

So a user can go to Outlook on the Web add an event to a group calendar and select Add Skype Meeting and save and it actually works. It never works across any of my tenants (I have tested on two at this point, with multiple accounts, multiple groups). We simply can't schedule an event via the web interface with a Skype meeting added to it.

I've been on twice with Office support about this and unfortunately they haven't been helpful. We've done several screen sharing sessions and I've shared the 500 internal server error that the website sends back to my browser but after two weeks of back and forth on the latest ticket, I'm not closer to a resolution.

This group calendar issue is significantly impacting a number of the teams that are using groups because we are all remote and always have to have a Skype meeting with our events.

[#4]

Did this ever reach a conclusion? https://support.office.com/en-us/article/Schedule-a-meeting-on-a-group-calendar-in-Outlook-0cf1ad68-... does not mention adding Skype for Business - seems limited to meetings in rooms.

On the web (Outlook.com) I cannot even see how to add a S4B to a calendar event even though I can add S4B as a Location or a Room - weird!

In Outlook 2016 client, if I open an event in the Group's calendar and try to add S4B I get a credential error because I am not "signed in" with the Group's email address. 

Any insight to help me get a Group meeting with S4B details in the invite?

David