Using Classic Outlook on Windows for personal email, calendar, and contact management
I just tested again on my test tenant and after I follow the steps the Report button is no longer showing in Classic Outlook. I had to restart Outlook after the change for it to take effect. Do you have anything setup different than I do? Make sure your tenant is signed into Office with the same tenant that you are making the changes for. Also, the Report button is currently available to 50% of Current Channel so not all machines will have it yet. If you need to make sure your machine, has it put it on Beta or CC Preview which are both at 100%.
I went to this page and signed in as Tenant Admin, https://security.microsoft.com/securitysettings/userSubmission
Below is how the page looked after I saved it.
I made sure I am on Current Channel latest build and my test tenant account is signed in. I have machines on CC Preview and Beta and I tested with those to and they behave the same.