When a user logs into Strategy Web, there are two timeout settings which come into play.
The first is the 'Clients Session Idle time (sec)' setting located in Workstation
by right-clicking the Environment -> Properties -> Governing Settings -> Clients Session Idle time (sec), as shown in the image below.


This setting limits the time, in seconds, that users can remain idle before their Strategy Intelligence Server session is ended.
The second setting is the session timeout on the web server side.
Using Strategy Web running on IIS, the session timeout is configured using IIS Manager as seen in step 2 of the following article "KB41860 - What are the timeout settings controlled by IIS 7 that affect MicroStrategy Web"
Note that the web server side session will also expire once the application pool is recycled.
Strategy Web on IIS saves the information for user sessions in a .NET session object. Active Server Page (ASP) .NET session objects provide their own session management and define a timeout after which the session object is released if it has not been accessed. This occurs independently of the value entered for the Strategy Intelligence Server's governing 'Web user session idle time' setting. Users are prompted for their login information because of a timeout of the session object in the .NET infrastructure. For Strategy Web Universal, contact the Web Administrator for information on Web Application specific timeout settings.
When using Strategy Web JSP, the session timeout is set in the web.xml file as described in the following article "KB12966: How to configure the web session timeout set on JSP application servers using MicroStrategy Web JSP ".Note that depending on the JSP application server, other web application server specific session timeout configurations may interfere. Refer to the documentation of the respective Web application server for more information.
A third security setting that should be kept in mind for session timeouts for Strategy Web is 'Allow automatic login if session is lost'. This setting can be found in the Security section on the Web Administration Page and looks like the image shared below:

This setting enables users to be automatically reconnected to the Strategy Intelligence Server if the session is lost. This setting will NOT automatically reconnect the .NET session object.
To fully understand how these settings interact with each other, read the following scenarios:
Scenario 1:
Web User Session Idle Time = 60 minutes Timeout setting in Web.config = 20 minutes Allow automatic login if session is lost = checked
Web User Session Idle Time = 20 minutes Timeout setting the Web.config file = 60 minutes Allow automatic login if session is lost = checked
Web User Session Idle Time = 20 minutes Timeout setting the Web.config file = 60 minutes Allow automatic login if session is lost = unchecked

KB12867