Hi @SCapo451 ,
Welcome!
According to my tests, using Outlook 365, once I enable the tracking option in GPO like your screenshot, after restarting the Outlook desktop client, the tracking options in Outlook would immediately turn grey like below:
And as I know, it is quite normal that those setting you configured will turn grey in Outlook. Outlook will follow the settings you configured in the GPO and those settings will be grayed out and cannot be changed. Many other Outlook settings(AutoArchive settings for example) in GPO will also greyed out, work the same. Not quite sure why this option would delay working in your organization but we indeed could not modify those settings in Outlook if you still keep your GPO settings.
As a workaround for emails that you do not would like Read Receipt, maybe you could edit and send them using web mail client, though indeed inconvenient.
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