If you want to transfer some files to your iPhone / iPad on Windows, you will have to SSH into your iDevice to gain the access to root folders. In this tutorial we will explain how to SSH into your iPad/iPhone using OpenSSH and WinSCP (for windows only). One more thing before the actual steps is that your device should be jailbroken because OpenSSH is available via Cydia Store only. There are different methods to jailbreak your iPhone and iPad like Redsnow and Spirit. Spirit is one of the best software for easy jailbreak of iPhone and iPad.
Step 1: After jailbreak press the Cydia icon your Springboard.
Step 2: On the bottom of screen click on “Section”.
Step 3: From the list of sections press “Networking” to get the list of networking related packages.
Step 4: Now select OpenSSH.
Step 5: At the top right of the screen there is “Install” button. Press it.
Step 6: Now press the “Confirm” button at the top right screen.
Step 7: After the installation has completed, press the large “Return to Cydia” button.
Step 8: Now hit the home button to go back to your springboard.
Step 9: Now we need to get the IP addrss of your iPhone/iPad. Open the Settings from springboard.
Step 10: Now press Wi-Fi from the settings.
Step 11: Make sure you are connected to the Wireless Network and press the circular blue arrow button.
Step 12: Take note of your IP address from the Wi-Fi details screen.
Step 13: Download WinSCP and install it on your Windows PC. You should be on the same Wireless network on which your iPhone/ipad is.
Step 14: Open the WinSCP and type the IP of iPhone/iPad in the “Host Name” field. Enter “root” as username and “alpine” as password and click “Login”.
Step 15: WinSCP will start connecting. If you see any dialogue box, click on “update” or “add”. Now you are connected and can transfer the files in the required folders of your iPhone/iPad.
As mentioned earlier this tutorial is for windows users, however if you are on Mac, you can head over to this post to SSH into iPad/iPhone. Jared has also shared another SSH app, other than OpenSSH, which is iSSH. You can also give it a try but it is paid.