I may have found a hint from some googling that readline will read in /etc/inputrc on login but if this is true, I am unsure what component of readline might I require to copy over from the live system into the chroot jail.
For reference, I include the tree view of the chroot jail I created below. Thank you kindly for any suggestions.
% tree -a /var/jail
/var/jail
├── .bashrc
├── bin -> usr/bin
├── dev
│ ├── null
│ ├── random
│ ├── tty
│ └── zero
├── etc
│ ├── group
│ ├── inputrc
│ ├── passwd
│ └── profile
├── lib -> usr/lib
├── lib64 -> usr/lib64
└── usr
├── bin
│ ├── bash
│ ├── ls
│ └── scp
├── lib
│ ├── libcap.so.2
│ ├── libc.so.6
│ ├── libdl.so.2
│ ├── libncursesw.so.6
│ ├── libnss3.so
│ ├── libnssckbi-p11-kit.so
│ ├── libnssckbi.so
│ ├── libnss_compat-2.23.so
│ ├── libnss_compat.so
│ ├── libnss_compat.so.2
│ ├── libnss_db-2.23.so
│ ├── libnssdbm3.chk
│ ├── libnssdbm3.so
│ ├── libnss_db.so
│ ├── libnss_db.so.2
│ ├── libnss_dns-2.23.so
│ ├── libnss_dns.so
│ ├── libnss_dns.so.2
│ ├── libnss_files-2.23.so
│ ├── libnss_files.so
│ ├── libnss_files.so.2
│ ├── libnss_hesiod-2.23.so
│ ├── libnss_hesiod.so
│ ├── libnss_hesiod.so.2
│ ├── libnss_myhostname.so.2
│ ├── libnss_mymachines.so.2
│ ├── libnss_nis-2.23.so
│ ├── libnss_nisplus-2.23.so
│ ├── libnss_nisplus.so
│ ├── libnss_nisplus.so.2
│ ├── libnss_nis.so
│ ├── libnss_nis.so.2
│ ├── libnss_resolve.so.2
│ ├── libnsssysinit.so
│ ├── libnssutil3.so
│ ├── libnss_winbind.so
│ ├── libnss_winbind.so.2
│ ├── libnss_wins.so
│ ├── libnss_wins.so.2
│ └── libreadline.so.6
└── lib64
└── ld-linux-x86-64.so.2
9 directories, 53 files
1. http://www.cyberciti.biz/faq/debian-ubuntu-restricting-ssh-user-session-to-a-directory-chrooted-jail/
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