There seems to be a lot of different SDKs / APIs around Skype for Business. I'm having a tough time deciphering which one would be appropriate for a server side Bot like application that could communicate domain specific information to the users within the organization. For example we'd like to be able to deliver task(s) via messages and perform presence based task assignment. This seems to be fairly low hanging fruit but where's the REST endpoints and documentation to make this happen. Assuming for example I wanted to create a little console application that could facilitate this what API would you recommend?
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I think both UCMA and UCWA can be used. However, considering you want a server application, UCWA seems fit the case. Here is the detail of SDK, you can find code samples at there: https://msdn.microsoft.com/en-us/library/office/mt650889(v=office.16).aspx
Here are the main differences between UCMA and UCWA:
UCMA is a .NET SDK that provides rich control over a Skype for Business server deployment. It enables applications to automatically route calls and messages, provide automatic responses (IVR or chat bots), record conversations etc. It can be used in a number of scenarios such as a 'contact center' application that distributes incoming calls to an available agent with the right skillset. UCMA applications are managed by running them on application servers that are activated as part of the Skype for Business server deployment. As such, UCMA is not available for Skype for Business Online (Office 365).
UCWA is a RESTful Web API that acts on behalf of a single Skype for Business user. It enables applications to send and receive messages for that user, read presence for their contacts, etc. Typically it is used for interactive "line of business" applications that want to embed Skype for Business messaging/presence. It is also possible to create a 'technical account', that doesn't correspond to a real person, and use UCWA in 'headless' server applications but this approach currently has authentication and scalability limitations. UCWA applications have no deployment constraints since UCWA is a regular RESTful Web API. It is available for both Skype for Business Server (get started) and for Skype for Business Online (get started). The latter has slightly fewer capabilities right now: - for example, messages can be sent but not received - though this should change soon.