It looks like Classic Start Menu is not loading for you reliably at startup. Which version of Windows are you running and which version of Classic Shell? Please download version 4.2.4:
http://www.classicshell.net/downloads/latest After installing it, open its settings and make sure the option "Start automatically for this user" is enabled on the General Behavior tab.
If it still does not load for you, go to C:\Program Files\Classic Shell from File Explorer and locate ClassicStartMenu.exe. Select ClassicStartMenu.exe and click Copy. Then immediately go to C:\Users\<your user name folder>\AppData\Roaming\Microsoft\Windows\Start Menu\Programs\Startup\. Right click in an empty area inside the Startup folder and click "Paste shortcut".
Now the Classic Start Menu should load automatically for you every time you sign in to Windows.