Always-On VPN with iPhone and iPad

NOTE: This How-to explains how to set up Always-On on your iPad or iPhone to get a permanent enforced VPN connection. To use this functionality, the device must be set to “supervised” mode. This process will reset the device to default settings. Before switching to supervised mode it is strongly recommended to make a backup of your iPad or iPhone.

Furthermore you will need a computer with MacOS X installed to run the Apple Configurator, which is necessary to switch the iPad/iPhone into supervised mode.

Alwasys-ON VPN only works with iOS 8.0 or higher.

Tip: If you don’t want to set your device to supervised mode, you can also use On-Demand VPN which provides a similar functionality.

Before continuing, backup your device first in case anything goes wrong or you want to revert the changes later. To do so, connect your device to your MacOS X computer, go into iTunes and choose “Back up Now” under the “Summary” of the device you want to back up. Also check “Encrypt local backup” if you want to also backup account passwords etc.

Should you use iCloud, deactivate “Find my iPad” (or iPhone) in your device settings, because you cannot go into supervised mode when this option is activated.

To do so, go in your iPad or iPhone settings, tap on “iCloud” and “Find my iPhone/iPad” and disable it.

Download and install the Apple Configurator 2 from the Apple AppStore.

Once installed, open the Apple Configurator. Make sure your iPhone or iPad is connected, then double click the device in the Apple Configurator. Next click “Prepare” and choose “Manual” configuration in the popup, then click “Next”.

In the next window, choose “Do not enroll in MDM” and click on “Next”. Make sure the checkbox for “Supervise devices” is checked and choose whether you want to “Allow devices to pair with other computers”. Continue by clicking “Next”.

In the next window, enter the information you want to use for your device.

In the “Create an Organization” dialogue choose “Generate a new supervision identity” and click “Next”. Finally leave the Setup Assistant to “Show all Steps” and click on “Prepare”.

Your iPad or iPhone is now being reset. This process can take a while.

In the “File” menu, choose “New Profile”. The configuration window will pop up.

Under “General” enter the information for the VPN server you want to connect to. The identifier can be any (unique) name, but we recommend using the server name for clarity. In our example we are using

Download the Perfect Privacy certificate (login required). Now choose “Certificates” on the left, click “Configure” and import the file perfect-privacy_ipsec_ca.crt from the downloaded zip archive.

Go to the “VPN” section on the left and click “Configure”.

Use the information shown in the screenshot on the left. For Account/Password enter your Perfect Privacy user credentials. If you leave “Local Identifier” empty, you will receive a warning that the profile is incomplete. However, you can safely ignore this warning. Alternatively you can copy the content from “Remote Identifier” into the “Local Identifier” field.

Then save the profile (“File” menu > “Save”). Now you can close the settings window.

Finally, in the Apple Configurator, apply the profile you just created via the “Actions” Menu > “Add” > “Profiles…” and choose the file you created earlier.

Since your device was reset you will now need to do the initial setup of your iPad or iPhone again.

Always-On VPN should now be functioning. A VPN symbol should appear in the top left whenever you have internet connection.

Verify that the VPN connection works properly by visiting our Check-IP website.

If you have any questions, comments or other feedback regarding this howto, please use the corresponding thread in our community forums.
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