Soon we'll be able to delete all sentry events at once. Hopefully they'll implement being able to select multiple events as well.
Yes
— Elon Musk (@elonmusk) October 14, 2020
Update: Tesla released the ability to delete all dashcam/sentry videos and many other new features in the 2021 Holiday Update. The holiday update was released with version 2021.44.25.
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