Unable to ssh root@localhost on jailbroken iPad with iOS 8.1
A much better alternative than to run Prompt as root, is to create another sshd instance listening to a port above 1024.

In this example I have used port 10022.


Copy /Library/LaunchDaemons/com.openssh.sshd.plist to /Library/LaunchDaemons/com.openssh.sshd2.plist
Change the Label and the SockServiceName in com.openssh.sshd2.plist by appending 2 to ssh / sshd:


com.openssh.sshd -> com.openssh.sshd2
ssh -> ssh2

Add the following lines to /etc/services:



ssh2              10022/udp     # SSH Remote Login Protocol
ssh2              10022/tcp     # SSH Remote Login Protocol


Differences for iOS versions:

iOS 12.1.2 / unc0ver, iOS 13.3.1 / checkra1n:


from this answer choice #2. 
copy the plist as above, but change the SockServiceName in com.openssh.sshd2.plist from ssh to simply the new port number 10022. The section will look like this:


&lt;key&gt;Sockets&lt;/key&gt;
&lt;dict&gt;
   &lt;key&gt;Listeners&lt;/key&gt;
   &lt;dict&gt;
      &lt;key&gt;SockServiceName&lt;/key&gt;
      &lt;string&gt;10022&lt;/string&gt;
   &lt;/dict&gt;
&lt;/dict&gt;


iOS 12.4 / chimera.sh


don't copy the plist file
instead, edit /etc/ssh/sshd_config as root. Details from this article
remove the comment in front of Port 22
add another line beneath for Port 10022


All iOS versions:


Reboot the device (or launchctl load com.openssh.sshd2.plist if you do not want to reboot)
Connect via port 10022 instead of 22




If you have installed bash, coreutils and sed you can automate it with this script:

#!/bin/bash
cd /Library/LaunchDaemons
cp com.openssh.sshd{,2}.plist
sed -i'' '/&lt;key&gt;Label&lt;\/key&gt;/{N;s/sshd/sshd2/}' com.openssh.sshd2.plist
sed -i'' '/&lt;key&gt;SockServiceName&lt;\/key&gt;/{N;s/ssh/ssh2/}' com.openssh.sshd2.plist

cd /etc
if ! grep ssh2 services; then
    cat &gt;&gt; services &lt;&lt;EOF
ssh2              10022/udp     # SSH Remote Login Protocol
ssh2              10022/tcp     # SSH Remote Login Protocol
EOF
fi