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If you arrived at this page then your Oak has likely tried to update from both the main update server, and the fallback slower but more reliable server, and neither has worked.
First we want to be clear: This update issue affects only the first update due to some issues with the firmware shipped on the first run of Oaks, after the first update all later updates will work on most networks without issue. We apologize for this issue and hope you will stick with us to get your Oak its first update which solves this issue from there forward.
We have found two methods for troubleshooting that we feel are worth the effort as the result in a very high rate of success. Thus far we are unaware of anyone who could not update after trying both of these methods and/or another WiFi network. Please try the method that seems most convenient (based on your knowledge of routers or computers) to you first, and then try the other method if that does not work.
Option 1: Using the local update tool