There are a couple circumstances that will result in the VPN Connection - Please enter your authentication information pop-up appearing.
1. Restoring from a non-encrypted backup:
Apple will not transfer sensitive information like your keychain or passwords if the backup is not encrypted. TunnelBear will need information from your keychain in order to authenticate your connection.
In this case, to get rid of the pop-up and get your Bear back to normal, simply dismiss the pop-up, delete TunnelBear from your device and reinstall it from the App Store.
2. TunnelBear connected when rebooting:
If you’ve not recently restored your device from a backup, it’s possible that TunnelBear is simply attempting to connect before your keychain is available. This means that your Bear will not be able to get your authentication information. This typically happens when you reboot your device while TunnelBear is connected.
In this case, to clear the pop-up, simply dismiss it by pressing cancel. Then, head into the TunnelBear app, it should connect automatically.
If you find that the issue continues to occur, we recommend that you disconnect from TunnelBear before rebooting your device.
Of course, if the issues persist, reach out to our support bears for further help!