Public bug reported:

root@root:~/sandbox# certutil -K -d .pki/nssdb/
certutil: Checking token "NSS Certificate DB" in slot "NSS User Private Key and 
Certificate Services"
Enter Password or Pin for "NSS Certificate DB":
< 0> rsa      04ff65bfa43d71346c786d78e48ff0f2c9fccc71   (orphan)
< 1> rsa      c89d0f0a39893f5636281e708434cb2521c9c7e0   1.2.3.4
< 2> rsa      323236d51ca7a59a6cffe8622acb6836db78e565   (orphan)
< 3> rsa      4dd54c6572610a2b41ef06aa93f1845e6def2d8c   2.3.4.37
< 4> rsa      a7180b2d9f5dbbbfeb018ed12de8bdbc474967ef   (orphan)
< 5> rsa      8323fde266d0db66c19fda80edc8aae50f365e06   (orphan)

root@root:~/sandbox# certutil -L -d .pki/nssdb/

Certificate Nickname                         Trust Attributes
                                                             SSL,S/MIME,JAR/XPI

1.2.3.4                                                    CTu,u,u
2.3.4.5                                                      u,u,u
2.3.4.7                                                      u,u,u
2.3.4.37                                                    u,u,u


root@root:~/sandbox# certutil -D -n 2.3.4.37 -d .pki/nssdb/

Here the cert got deleted

root@root:~/sandbox# certutil -L -d .pki/nssdb/

Certificate Nickname                         Trust Attributes
                                                             SSL,S/MIME,JAR/XPI

1.2.3.4                                                    CTu,u,u
2.3.4.5                                                      u,u,u
2.3.4.7                                                      u,u,u


But the private key did not get which is expected I believe as I just deleted 
only the cert

root@root:~/sandbox# certutil -K -d .pki/nssdb/
certutil: Checking token "NSS Certificate DB" in slot "NSS User Private Key and 
Certificate Services"
Enter Password or Pin for "NSS Certificate DB":
< 0> rsa      04ff65bfa43d71346c786d78e48ff0f2c9fccc71   (orphan)
< 1> rsa      c89d0f0a39893f5636281e708434cb2521c9c7e0   1.2.3.4
< 2> rsa      323236d51ca7a59a6cffe8622acb6836db78e565   (orphan)
< 3> rsa      4dd54c6572610a2b41ef06aa93f1845e6def2d8c   2.3.4.37
< 4> rsa      a7180b2d9f5dbbbfeb018ed12de8bdbc474967ef   (orphan)
< 5> rsa      8323fde266d0db66c19fda80edc8aae50f365e06   (orphan)


So I attempted to delete the corresponding key

root@root:~/sandbox# certutil -F -n 2.3.4.37 -d .pki/nssdb/
Enter Password or Pin for "NSS Certificate DB":

But it did not delete as can be seen below.

root@root:~/sandbox# certutil -K -d .pki/nssdb/ -f .pki/conf/pwdfile.txt 
certutil: Checking token "NSS Certificate DB" in slot "NSS User Private Key and 
Certificate Services"
< 0> rsa      04ff65bfa43d71346c786d78e48ff0f2c9fccc71   (orphan)
< 1> rsa      c89d0f0a39893f5636281e708434cb2521c9c7e0   1.2.3.4
< 2> rsa      323236d51ca7a59a6cffe8622acb6836db78e565   (orphan)
< 3> rsa      4dd54c6572610a2b41ef06aa93f1845e6def2d8c   2.3.4.37
< 4> rsa      a7180b2d9f5dbbbfeb018ed12de8bdbc474967ef   (orphan)
< 5> rsa      8323fde266d0db66c19fda80edc8aae50f365e06   (orphan)

Only way I can get the key deleted is by executing a "-F key deletion"
on a key whose cert has not already been deleted. This however removes
the corresponding cert also. I know there is a bug on 'being unable to
delete a orphan key'. But I thought this is a distinct interesting
behavior.


=========

lsb_release -rd
Description:    Ubuntu 12.04.5 LTS
Release:        12.04

=========

dpkg -l | grep nss
ii  insserv                          1.14.0-2.1ubuntu2                 Tool to 
organize boot sequence using LSB init.d script dependencies
ii  libnss3                          3.17-0ubuntu0.12.04.1             Network 
Security Service libraries
ii  libnss3-1d                       3.17-0ubuntu0.12.04.1             Network 
Security Service libraries
ii  libnss3-tools                    3.17.1-0ubuntu0.12.04.1           Network 
Security Service tools
ii  openssh-client                   1:5.9p1-5ubuntu1.4                secure 
shell (SSH) client, for secure access to remote machines
ii  openssh-server                   1:5.9p1-5ubuntu1.4                secure 
shell (SSH) server, for secure access from remote machines
ii  openssl                          1.0.1-4ubuntu5.17                 Secure 
Socket Layer (SSL) binary and related cryptographic tools

** Affects: nss (Ubuntu)
     Importance: Undecided
         Status: New


** Tags: certutil nss pki

-- 
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https://bugs.launchpad.net/bugs/1377284

Title:
  Cannot delete a private key using certutil -F

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