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As regular Skype doesn't support sending generated messages and calls through the Skype4COM.dll, I'm wondering if that would be possible with Skype for Business (SfB)?

The way it worked before was that we had a FormApplication that selected important data from the MySQL database. If the record retrieved was "Urgent" it called/sendMsg to a person/people. Now as that doesn't work any longer we'd need some other solution. So I'm asking for a bit of advice how to go on forward.

SfB seems to have a lot of limitations in regards to communicating with regular Skype users so I'm wondering if this is even possible? Is sending out a group message to everyone possible? I read that calls aren't possible for more than 1 regular Skype user at a time from SfB.

What would be the best approach to notify users to their mobile device straight away (besides sending e-mail) if a record is changed to/fetched as "Urgent"?

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Skype for Business (SfB) and Skype for Consumer (SfC) are mostly two different products. You can build a federation from a SfB environment towards a SfC environment. Then you can perform e.g. chats between SfB and SfC users and via versa.

A typical SfB environment has the following server: 1-2 Edge Server 3 Frontend Server (+ collocated with mediation service) 1 Reverse Proxy (e.g. an Microsoft Web Application Proxy) 1 SQL Enterprise Server

I do not think that using SfB will solve your issues as this construct isn“t a "cheap" solution to solve your "issues". You can try to use "Skype Online" which is the cloud version from SfB but not sure if that might work for your "development".

With SfB you can perform a call with multiple persons (depending on the SfB client licence) that's not an issue.

If it needs to be simple and free you might wish to build something with XMPP and an Jabber Client. There are some good libs out there.