Why does SSH ask for password as one user and not another?

My SSH config contains two entries to SSH into the same host with different usernames

Host babyroot
  Hostname XXX.XXX.XXX.XXX
  User root
  ServerAliveInterval 300
  IdentityFile ~/.ssh/id_rsa
  ForwardAgent yes

  Host babyubuntu
  Hostname XXX.XXX.XXX.XXX
  User ubuntu
  ServerAliveInterval 300
  IdentityFile ~/.ssh/id_rsa
  ForwardAgent yes

ssh babyroot let's me in fine.

ssh babyubuntu asks for a password.

On the remote machine roots .ssh directory looks like this:

http://ift.tt/12pjtjo

and ubuntus .ssh looks like this:

http://ift.tt/1FM4azA

Both authorized_key are identical

ssh babyroot -vvv gives

OpenSSH_6.2p2, OSSLShim 0.9.8r 8 Dec 2011
debug1: Reading configuration data /Users/XXX/.ssh/config
debug1: /Users/XXX/.ssh/config line 1: Applying options for *
debug1: /Users/XXX/.ssh/config line 293: Applying options for babyroot
debug1: Reading configuration data /etc/ssh_config
debug1: /etc/ssh_config line 20: Applying options for *
debug1: auto-mux: Trying existing master
debug2: fd 3 setting O_NONBLOCK
debug2: mux_client_hello_exchange: master version 4
debug3: mux_client_forwards: request forwardings: 0 local, 0 remote
debug3: mux_client_request_session: entering
debug3: mux_client_request_alive: entering
debug3: mux_client_request_alive: done pid = 45382
debug3: mux_client_request_session: session request sent
debug1: mux_client_request_session: master session id: 2
Last login: Tue Dec  2 18:51:29 2014 from YYY
root@baby:~# 

where as ssh babyubuntu -vvv gives

OpenSSH_6.2p2, OSSLShim 0.9.8r 8 Dec 2011
debug1: Reading configuration data /Users/XXX/.ssh/config
debug1: /Users/XXX/.ssh/config line 1: Applying options for *
debug1: /Users/XXX/.ssh/config line 300: Applying options for babyubuntu
debug1: Reading configuration data /etc/ssh_config
debug1: /etc/ssh_config line 20: Applying options for *
debug1: auto-mux: Trying existing master
debug1: Control socket "/Users/XXX/.ssh/sockets/ubuntu@AAA" does not exist
debug2: ssh_connect: needpriv 0
debug1: Connecting to XXX [XXX] port 22.
debug1: Connection established.
debug3: Incorrect RSA1 identifier
debug3: Could not load "/Users/XXX/.ssh/id_rsa" as a RSA1 public key
debug1: identity file /Users/XXX/.ssh/id_rsa type 1
debug1: identity file /Users/XXX/.ssh/id_rsa-cert type -1
debug1: Enabling compatibility mode for protocol 2.0
debug1: Local version string SSH-2.0-OpenSSH_6.2
debug1: Remote protocol version 2.0, remote software version OpenSSH_6.6.1p1 Ubuntu-2ubuntu2
debug1: match: OpenSSH_6.6.1p1 Ubuntu-2ubuntu2 pat OpenSSH*
debug2: fd 3 setting O_NONBLOCK
debug3: load_hostkeys: loading entries for host "XXX" from file "/Users/XXX/.ssh/known_hosts"
debug3: load_hostkeys: found key type RSA in file /Users/XXX/.ssh/known_hosts:2
debug3: load_hostkeys: loaded 1 keys
debug3: order_hostkeyalgs: prefer hostkeyalgs: ssh-rsa-cert-v01@openssh.com,ssh-rsa-cert-v00@openssh.com,ssh-rsa
debug1: SSH2_MSG_KEXINIT sent
debug1: SSH2_MSG_KEXINIT received
debug2: kex_parse_kexinit: diffie-hellman-group-exchange-sha256,diffie-hellman-group-exchange-sha1,diffie-hellman-group14-sha1,diffie-hellman-group1-sha1
debug2: kex_parse_kexinit: ssh-rsa-cert-v01@openssh.com,ssh-rsa-cert-v00@openssh.com,ssh-rsa,ssh-dss-cert-v01@openssh.com,ssh-dss-cert-v00@openssh.com,ssh-dss
debug2: kex_parse_kexinit: aes128-ctr,aes192-ctr,aes256-ctr,arcfour256,arcfour128,aes128-gcm@openssh.com,aes256-gcm@openssh.com,aes128-cbc,3des-cbc,blowfish-cbc,cast128-cbc,aes192-cbc,aes256-cbc,arcfour,rijndael-cbc@lysator.liu.se
debug2: kex_parse_kexinit: aes128-ctr,aes192-ctr,aes256-ctr,arcfour256,arcfour128,aes128-gcm@openssh.com,aes256-gcm@openssh.com,aes128-cbc,3des-cbc,blowfish-cbc,cast128-cbc,aes192-cbc,aes256-cbc,arcfour,rijndael-cbc@lysator.liu.se
debug2: kex_parse_kexinit: hmac-md5-etm@openssh.com,hmac-sha1-etm@openssh.com,umac-64-etm@openssh.com,umac-128-etm@openssh.com,hmac-sha2-256-etm@openssh.com,hmac-sha2-512-etm@openssh.com,hmac-ripemd160-etm@openssh.com,hmac-sha1-96-etm@openssh.com,hmac-md5-96-etm@openssh.com,hmac-md5,hmac-sha1,umac-64@openssh.com,umac-128@openssh.com,hmac-sha2-256,hmac-sha2-512,hmac-ripemd160,hmac-ripemd160@openssh.com,hmac-sha1-96,hmac-md5-96
debug2: kex_parse_kexinit: hmac-md5-etm@openssh.com,hmac-sha1-etm@openssh.com,umac-64-etm@openssh.com,umac-128-etm@openssh.com,hmac-sha2-256-etm@openssh.com,hmac-sha2-512-etm@openssh.com,hmac-ripemd160-etm@openssh.com,hmac-sha1-96-etm@openssh.com,hmac-md5-96-etm@openssh.com,hmac-md5,hmac-sha1,umac-64@openssh.com,umac-128@openssh.com,hmac-sha2-256,hmac-sha2-512,hmac-ripemd160,hmac-ripemd160@openssh.com,hmac-sha1-96,hmac-md5-96
debug2: kex_parse_kexinit: none,zlib@openssh.com,zlib
debug2: kex_parse_kexinit: none,zlib@openssh.com,zlib
debug2: kex_parse_kexinit: 
debug2: kex_parse_kexinit: 
debug2: kex_parse_kexinit: first_kex_follows 0 
debug2: kex_parse_kexinit: reserved 0 
debug2: kex_parse_kexinit: curve25519-sha256@libssh.org,ecdh-sha2-nistp256,ecdh-sha2-nistp384,ecdh-sha2-nistp521,diffie-hellman-group-exchange-sha256,diffie-hellman-group-exchange-sha1,diffie-hellman-group14-sha1,diffie-hellman-group1-sha1
debug2: kex_parse_kexinit: ssh-rsa,ssh-dss,ecdsa-sha2-nistp256
debug2: kex_parse_kexinit: aes128-ctr,aes192-ctr,aes256-ctr,arcfour256,arcfour128,aes128-gcm@openssh.com,aes256-gcm@openssh.com,chacha20-poly1305@openssh.com,aes128-cbc,3des-cbc,blowfish-cbc,cast128-cbc,aes192-cbc,aes256-cbc,arcfour,rijndael-cbc@lysator.liu.se
debug2: kex_parse_kexinit: aes128-ctr,aes192-ctr,aes256-ctr,arcfour256,arcfour128,aes128-gcm@openssh.com,aes256-gcm@openssh.com,chacha20-poly1305@openssh.com,aes128-cbc,3des-cbc,blowfish-cbc,cast128-cbc,aes192-cbc,aes256-cbc,arcfour,rijndael-cbc@lysator.liu.se
debug2: kex_parse_kexinit: hmac-md5-etm@openssh.com,hmac-sha1-etm@openssh.com,umac-64-etm@openssh.com,umac-128-etm@openssh.com,hmac-sha2-256-etm@openssh.com,hmac-sha2-512-etm@openssh.com,hmac-ripemd160-etm@openssh.com,hmac-sha1-96-etm@openssh.com,hmac-md5-96-etm@openssh.com,hmac-md5,hmac-sha1,umac-64@openssh.com,umac-128@openssh.com,hmac-sha2-256,hmac-sha2-512,hmac-ripemd160,hmac-ripemd160@openssh.com,hmac-sha1-96,hmac-md5-96
debug2: kex_parse_kexinit: hmac-md5-etm@openssh.com,hmac-sha1-etm@openssh.com,umac-64-etm@openssh.com,umac-128-etm@openssh.com,hmac-sha2-256-etm@openssh.com,hmac-sha2-512-etm@openssh.com,hmac-ripemd160-etm@openssh.com,hmac-sha1-96-etm@openssh.com,hmac-md5-96-etm@openssh.com,hmac-md5,hmac-sha1,umac-64@openssh.com,umac-128@openssh.com,hmac-sha2-256,hmac-sha2-512,hmac-ripemd160,hmac-ripemd160@openssh.com,hmac-sha1-96,hmac-md5-96
debug2: kex_parse_kexinit: none,zlib@openssh.com
debug2: kex_parse_kexinit: none,zlib@openssh.com
debug2: kex_parse_kexinit: 
debug2: kex_parse_kexinit: 
debug2: kex_parse_kexinit: first_kex_follows 0 
debug2: kex_parse_kexinit: reserved 0 
debug2: mac_setup: found hmac-md5-etm@openssh.com
debug1: kex: server->client aes128-ctr hmac-md5-etm@openssh.com none
debug2: mac_setup: found hmac-md5-etm@openssh.com
debug1: kex: client->server aes128-ctr hmac-md5-etm@openssh.com none
debug1: SSH2_MSG_KEX_DH_GEX_REQUEST(1024<1024<8192) sent
debug1: expecting SSH2_MSG_KEX_DH_GEX_GROUP
debug2: dh_gen_key: priv key bits set: 109/256
debug2: bits set: 520/1024
debug1: SSH2_MSG_KEX_DH_GEX_INIT sent
debug1: expecting SSH2_MSG_KEX_DH_GEX_REPLY
debug1: Server host key: RSA 84:cd:56:8f:f7:as:45:58:ee:ds:91:9a:f6:fd:6d:6a
debug3: load_hostkeys: loading entries for host "XXX" from file "/Users/XXX/.ssh/known_hosts"
debug3: load_hostkeys: found key type RSA in file /Users/XXX/.ssh/known_hosts:2
debug3: load_hostkeys: loaded 1 keys
debug1: Host '162.243.238.160' is known and matches the RSA host key.
debug1: Found key in /Users/XXX/.ssh/known_hosts:2
debug2: bits set: 515/1024
debug1: ssh_rsa_verify: signature correct
debug2: kex_derive_keys
debug2: set_newkeys: mode 1
debug1: SSH2_MSG_NEWKEYS sent
debug1: expecting SSH2_MSG_NEWKEYS
debug2: set_newkeys: mode 0
debug1: SSH2_MSG_NEWKEYS received
debug1: Roaming not allowed by server
debug1: SSH2_MSG_SERVICE_REQUEST sent
debug2: service_accept: ssh-userauth
debug1: SSH2_MSG_SERVICE_ACCEPT received
debug2: key: /Users/XXX/.ssh/id_rsa (0x7fb9cb501f70), explicit
debug1: Authentications that can continue: publickey,password
debug3: start over, passed a different list publickey,password
debug3: preferred publickey,keyboard-interactive,password
debug3: authmethod_lookup publickey
debug3: remaining preferred: keyboard-interactive,password
debug3: authmethod_is_enabled publickey
debug1: Next authentication method: publickey
debug1: Offering RSA public key: /Users/XXX/.ssh/id_rsa
debug3: send_pubkey_test
debug2: we sent a publickey packet, wait for reply
debug1: Authentications that can continue: publickey,password
debug2: we did not send a packet, disable method
debug3: authmethod_lookup password
debug3: remaining preferred: ,password
debug3: authmethod_is_enabled password
debug1: Next authentication method: password
ubuntu@XXX's password: