Why does the prompt look different for both Classic and New Outlook / OWA?

If the classic prompt still displays on Classic, you will need to disable the Com-addin so the M365 prompt shows. 

Step 1: Click on File
Step 2: Click on Options
Step 3: Click on Add-ins
Step 4: Click “Go”
Step 5: Scroll down to SendGuard for Outlook and disable the addin
Step 6: Click OK.