A quick question:
Do I need to buy an Apple Developer Program membership/certification ($99/yr) for testing via TestFlight?
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Yes. The reason is because TestFlight needs a valid ad hoc distribution provisioning profile to be submitted along with the binary. And you can’t create the provisioning profile without an iOS Developer Account.
PS: Just being a team member in someone else’s iOS Developer Team does not help. To create distribution profiles you need to be a team agent.
Edit:
Updating this answer, since Apple has acquired Testflight and the service is part of iTunes. You now definitely need to be in the iOS Developer program to send builds through Testflight 🙂
Another alternative is Crashlytics Beta if Testflight is not your thing.