1. I'm assuming you're playing D&D 5th edition using the D&D 5E By Roll20 character sheet. 2. I'm assuming you're opening up the character sheet and clicking on various rolls there and not using a macro. 3. If you open up a character sheet and click on the settings gear icon, what is 'Whisper Rolls to GM' set to? It should be set as 'Always Whisper Rolls' or 'Query Whisper'. 4. Are the rolls being output in a whisper? You should be able to see that yourself -- it'll have a yellow colored background instead of grey or blue. 5. Are your players set as GMs? If you want to change all NPC sheets to be 'Always Whisper Rolls', you can follow these steps from keithcurtis: A guide to whisper settings : Note that the whisper settings are attached to each individual sheet, there is no actual game setting. These instructions are for changing the defaults for all the character sheets in the game, then applying the settings to all existing sheets. Note that this will also change your PC sheets - you will have to manually change them to a different setting if one is preferred. Here are the ways to toggle this behavior: Always Whisper Go to the Campaign Settings Page Choose "Always Whisper Rolls" under "WHISPER ROLLS TO GM" in the Default Sheet Settings Save Load your game Go to the settings tab on the right and scroll to the bottom where you will find a button that says Apply Default Settings. Press it. Choose to update the Whisper settings. Wait a minute or two for it to resolve. There is a thin easy-to-miss progress bar. Never Whisper There's a bug in the game settings that doesn't recognize "Never Whisper Rolls", possibly because it is trying to write a blank value. The solution is to use Whisper Toggle. The default is public, so once this is set, all rolls should show. Go to the Campaign Settings Page Choose "Whisper Toggle" under "WHISPER ROLLS TO GM" in the Default Sheet Settings Save Load your game Go to the settings tab on the right and scroll to the bottom where you will find a button that says Apply Default Settings. Press it. Choose to update the Whisper settings. Wait a minute or two for it to resolve. There is a thin easy-to-miss progress bar. Query Whisper The default is public, so once this is set, all rolls should show by default unless you choose otherwise. Go to the Campaign Settings Page Choose "Query Whisper" under "WHISPER ROLLS TO GM" in the Default Sheet Settings Save Load your game Go to the settings tab on the right and scroll to the bottom where you will find a button that says Apply Default Settings. Press it. Choose to update the Whisper settings. Wait a minute or two for it to resolve. There is a thin easy-to-miss progress bar. Have fun!