I'm trying to add a user with a Technical Role to my iTunes Connect account so they can beta test my app through Test Flight, but the Technical Role seems to be missing in the following screenshot:

Did Apple remove this role or change the way Beta Testing works? If so, what did they replace it with?
Use App Manager instead of Technical. You can also invite beta tester from Test Flight --> External Testers --> + (Add New). They will be notified to their email. They can download app from TestFlight by clicking the app link as provided on email or directly from TestFlight notification.
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