SYMPTOM :
A Strategy Intelligence Server service is configured to start automatically, as shown below:

However, the following error is generated in the System log of the Microsoft Windows Event Viewer upon Windows start up:
Timeout (30000 milliseconds) waiting for the Strategy Intelligence Server service to connect
Users are forced to start the Strategy Intelligence Server manually.
CAUSE :
This issue occurs because the Strategy Intelligence Server must start after its associated database service has started.
Although the database service (Microsoft SQLServer in this example) is also configured to start up automatically, the database service takes longer to start, open the databases, run a recovery on the databases, etc..., than the amount of time allowed to the Strategy Intelligence Server service before it times out.
WORKAROUND :
Change the recovery properties of the Strategy Intelligence Server service to "Restart the Service," as shown below:

Allow Strategy Intelligence Server to attempt to restart after failures. Setting a two-minute wait until the service attempts to restart itself, as well as applying this setting for the second and subsequent failures to restart, will allow up to six minutes from the first service start attempt before the Strategy Intelligence Server service truly fails. This should provide extra time for the database service to start up.