By default, Whonixcheck runs automatically from time to time whenever the user starts up a Whonix-Workstation (commonly called whonix-ws). Whonixcheck verifies that the Whonix system is up-to-date and that everything is in proper working order.
Even though Whonixcheck should run automatically and periodically,  users can also manually run Whonixcheck to check the system status by following the directions below.
How to Manually Run Whonixcheck
Depending on the system specifications, Whonixcheck may take up to a few minutes to run. Assuming everything is working as intended, the output should highlight each "INFO" heading in green (not red). A successful Whonixcheck process results in output similar to the sample below.
Sample Whonixcheck Output
INFO: SocksPort Test Result: Connected to Tor. IP: 126.96.36.199 INFO: TransPort Test Result: Connected to Tor. IP: 188.8.131.52 INFO: Stream Isolation Test Result: Functional. INFO: Whonix News Result: √ Up to date: whonix-workstation-packages-dependencies 3.4.2-1 INFO: Debian Package Update Check Result: No updates found via apt-get. INFO: Whonix APT Repository: Enabled. When the Whonix team releases JESSIE updates, they will be AUTOMATICALLY installed (when you run apt-get dist-upgrade) along with updated packages from the Debian team. Please read https://www.whonix.org/wiki/Trust to understand the risk. If you want to change this, use: dom0 -> Start Menu -> Template: whonix-ws -> Whonix Repository
Tor bootstrap refers to the process of attempting to connect to the Tor network (successfully or unsuccessfully). Familiar output related to this process includes: "Tor connecting xx percent...", "Tor not connected", "Tor connected" and so on. Bootstrapping does not refer to related concepts, such as whether connections are "secure", "not secure", "anonymous" or "not anonymous".