The Calculation in the "Current Assigned Group" and "Current Assigned Analyst" fields on the Incident window is showing old information.
First thing to check is that the Calculation itself is correct, which you can do from here.
If the Calculation still shows old data, please see below:
The problem is most likely that the User's local machine has a slight time different to the Server's time.
So if an Analyst for example performs an action which will create an automatic assignment, the 'creation date' of the automatic Assignment will be the current time of the server.
If then the Analyst decide to create a new manual assignment directly after, the 'creation date' of the manually added assignment will be the current time of the user's machine from when the Assignment window was launched.
If this all happens within the space of 5 sec and the user's machine's time is no more than 30 sec behind in time from the server, the manually added assignment's 'creation date' will still be before the automated Assignment.
The Calculation will pick up the latest Assignment by looking on the Creation Date and so the automatic assignment will be the last one, hence this is the information you are seeing in the "Current Assigned Group" and "Current Assigned Analyst" fields
Please note that this will also affect placeholders and runtime values in the same way as these too are picking up the data depending on the "creation date" of the Collection its looking at.
To fix, please make sure that your client machines date and time is synchronized with the Server. This can be synchronized with Microsoft to make it easier.