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Developer Mode disappeared after tapping "Cancel" (iPadOS 27 Beta 3 & Beta 4) #29

Description

@29np5vvp28-svg

Device

  • iPad (9th generation)

iPadOS

  • iPadOS 27 Developer Beta 4
  • The same issue also occurred on Beta 3.

SideInstaller

  • Latest release

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

  1. Install SideInstaller on iPadOS 27.
  2. Start the pairing process.
  3. When the Developer Mode prompt appears, tap Cancel.
  4. 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?

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