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I recall I specd a font one time that is not on some systems and my app would not start up right and it took a long time to find a thing was erring on the font and the entire form loaded wrong after that and on and on. You could be skipping over entire sections due to an error. Msgbox("settings file read: variable 1 = " & var1.tostring) Add comments in your code you will disable later you can have lots of errors you never realize even if you do what you say. Remove all your try catch things you added. "I thought maybe it was some issue with the application starting before Windows had finished loading, so I added a thread.sleep for testing prior the Form.Load Event but still the same." You can also click the sync button on the settings page it deletes the old settings file. I notice that as I add or change settings and distribute to existing systems sometimes it gets enough out of sync that the app gets funny things happening the wrong way. Settings are saved as they are changed.Long shot: delete your entire user settings folder for that app and see if it changes anything.

I don't have any additional code to auto save settings on shutdown. When I manually open the application the variables are set as expected.

Correct - When the application is opened automatically on Windows startup they are nothing for the strings and false for the booleans.