Legacy Jailbreak

Hi folks, I'm a tinkerer and like to hack old devices. Currently running postmarketOS on an old oneplus6. Now I want to try to repurpose my old ipad 3 with LTE.

Edit: The problem might be the windows vm since an iphone 11 with linghtning cable also doesnt get recognized.

For that purpose I have tried:

• https://jailbreaks.app/legacy.html -> phoenix (Error: app could not be installed at this time)
• windows VM (I'm on linux) with usb connect, I can see the ipad in device manager and open the harddrive but neither itunes nor sideloadly will connect to it. impactor also wont recognize the device
• exchanging the cable for a different (newer) one, also no change
• resetting the ipad to factory settings to free up space, no change
• reinstalling itunes, icloud, sideloadly
• restarting between each step

I'm kind of running out of ideas at this point. I generally have a debug device which I could try and use on the ipad but I struggle to find resources on lower level hardware hacking for the ipad. Let me know if you have any other ideas.

Have a good one!

If you stumble into this post, chances are you have scoured the internet for solutions to this issue. The few mentions of it out there are answered with completely worthless "turn it off an on again" answers.

Well after spending a few evenings picking apart this issue I finally was able to add an Outlook account using the settings app on my iPad 4 running iOS 10.3.4.

TL:DR

• Install version .12 of ssl-kill-switch2 from their repo
• Add your account :)
• Remove ssl-kill-switch2

Background

Without the above steps, if you try to add an Outlook.com account to your device within the settings app, you would only see a blank WebView splash for half a second, and then it closes. This leaves you with a null account that doesn't work. As you can see, there's not much to go on, and the internet won't be of any help as stated.

Up until a few days ago a workaround was to add your Outlook account under the Microsoft Exchange option (using an app password). However this began failing recently. Currently this approach will yield intermittent "Incorrect Password" popups (even on current iOS versions). I suspect a recent change from Microsoft broke this workaround.

Unfortunately, iOS 10 forces you to use OAuth flow to add Outlook accounts. On earlier versions, there's no issue as you can simply provide an app password to the iOS login form and be on your way.

With these conditions, the only other way to add an Outlook Account is as a manually configured IMAP email. This will provide mail, but does not include Contacts or Calendar sync. It also doesn't support Push syncing.

Investigating the issue

Without much to go on with, I suspected Microsoft was rejecting the request (as the Google & Yahoo options did not immediately close). Therefore I started sniffing HTTPS requests from iOS through mitmproxy. This revealed that iOS first makes a CONNECT request to newaccountredirectdomain.apple.com when you try adding an Outlook account. This is the only request I saw, so my iPad was not even reaching Microsoft at all before kicking me out of the authentication flow. Other account options (Gmail, Yahoo) make a call to gil.apple.com and do continue afterwards with requests to google or yahoo.

I started reading up on similar issues, and they all pointed to certificate pinning being the culprit. This eventually led me to installing ssl-kill-switch2. It appears the Settings app implements some certificate pinning. Basically the settings App has defined certificates it expects the remote servers to present, any other certificate means the connection will be dropped.

I was then led to a bunch of time waste and headaches, because the latest version of ssl-kill-switch does not properly work on iOS 10, and there's no mention of this anywhere. Ssl-kill-switch2 has hardly been properly maintained, and through some open issues I started to suspect the latest version didn't actually work (on iOS 10 at least).

Therefore I installed v.12, did a respring, and tried adding an Outlook account. I could see that the WebView started and finally presented the Microsoft login web form. It accepted my credentials and a few seconds later I had my account added.

That's about it, hopefully someone with the same issue stumbles upon this post, and saves all the time I spent on this lmao.

(App Store) 1. Install the YouTube app via App Store or IPA Installer 2. Install iFile from Cydia 3. Go to iFile and navigate to applications folder

4. Go through every single folder in the directory until you find a folder called "YouTube.app"

5. Scroll down to a file called "info.plist" and change the version number that can still connect to YouTube servers with no issue (there will be 3 strings you have to change)

6. Install "Gsigninfix"

7. Install Tubefixer form the repo 'cydia.invoxiplaygames.uk' or 'cydia.invoxiplaygames.uk/beta'

8. Install "mikoto" from repo "cydia.akemi.ai"

9. Go to the Settings app and scroll down to mikoto and click it

10. Go to Youtube and click it and enable all the options shown.

(Preinstalled) 1. https://www.youtube.com/watch?v=N0Tg9TxLUGc&feature=youtube_gdata_player

2. This works on iOS 4 - 6 idk if this works on iPhone OS 3 or older.

Well, the description is still directly copied from Reddit (with no edits) and no one is actively posting. Will you move the Reddit members soon? Would love to see this active. Maybe you remember me. I caused some trouble on r/LegacyJailbreak before. But thought I would offer myself as a mod for this community anyways. I would call myself quite dedicated and active. If you look at [email protected], you see a great introduction to iDevice collecting and Jailbreaking. But anyways. Moving the community would be the next right step.

• Justus ;)