Device
iPadOS
- iPadOS 27 Developer Beta 4
- The same issue also occurred on Beta 3.
SideInstaller
Description
When I first attempted to enable Developer Mode, I accidentally tapped "Cancel" on the Developer Mode prompt.
After that, the Developer Mode option completely disappeared from Settings → Privacy & Security and has never come back.
Because of this:
- SideInstaller cannot complete pairing.
- Pairing always asks me to enable Developer Mode.
- Tapping "Pairing" does not re-trigger the Developer Mode prompt.
- LocalDevVPN works correctly.
- SideInstaller launches normally.
- Other sideloaded apps (SideStore, Feather, LiveContainer, KSign) also work normally.
The only thing preventing pairing is that Developer Mode is no longer available in Settings.
Steps to reproduce
- Install SideInstaller on iPadOS 27.
- Start the pairing process.
- When the Developer Mode prompt appears, tap Cancel.
- Open Settings → Privacy & Security.
Expected behavior
Developer Mode should either:
- remain available in Settings, or
- be shown again when attempting to pair with SideInstaller.
Actual behavior
Developer Mode disappears completely after tapping "Cancel" once and never comes back, making pairing impossible.
What I tried
- Restarted the iPad.
- Updated from iPadOS 27 Beta 3 to Beta 4.
- Tried pairing again.
- LocalDevVPN is working correctly.
None of these restored the Developer Mode option.
Additional information
- Device: iPad 9th generation
- No Mac available
- I would like to pair directly from the iPad if possible.
Is this a known issue? Is there any way to re-trigger the Developer Mode prompt without restoring the device or using Xcode?
Device
iPadOS
SideInstaller
Description
When I first attempted to enable Developer Mode, I accidentally tapped "Cancel" on the Developer Mode prompt.
After that, the Developer Mode option completely disappeared from Settings → Privacy & Security and has never come back.
Because of this:
The only thing preventing pairing is that Developer Mode is no longer available in Settings.
Steps to reproduce
Expected behavior
Developer Mode should either:
Actual behavior
Developer Mode disappears completely after tapping "Cancel" once and never comes back, making pairing impossible.
What I tried
None of these restored the Developer Mode option.
Additional information
Is this a known issue? Is there any way to re-trigger the Developer Mode prompt without restoring the device or using Xcode?