Steve,

two simultaneous ssh's to a server with already mounted encrypted partitions do 
not print errors for the user. 
However, auth.log records the following lines:

May  8 23:11:17 myserver sshd[22228]: Accepted password for myuser from 
xxx.xxx.xxx.xxx port 36342 ssh2
May  8 23:11:17 myserver sshd[22228]: pam_unix(sshd:session): session opened 
for user myuser by (uid=0)
May  8 23:11:17 myserver sshd[22228]: pam_mount(mount.c:69): Messages from 
underlying mount program:
May  8 23:11:17 myserver sshd[22228]: pam_mount(mount.c:73): 
crypt_activate_by_passphrase: File exists
May  8 23:11:17 myserver sshd[22228]: pam_mount(pam_mount.c:521): mount of 
/dev/myvolumehere/mypartitionhere failed
May  8 23:11:33 myserver sshd[22472]: Accepted password for myuser from 
xxx.xxx.xxx.xxx port 36343 ssh2
May  8 23:11:33 myserver sshd[22472]: pam_unix(sshd:session): session opened 
for user myuser by (uid=0)
May  8 23:11:33 myserver sshd[22472]: pam_mount(mount.c:69): Messages from 
underlying mount program:
May  8 23:11:33 myserver sshd[22472]: pam_mount(mount.c:73): 
crypt_activate_by_passphrase: File exists
May  8 23:11:33 myserver sshd[22472]: pam_mount(pam_mount.c:521): mount of 
/dev/myvolumehere/mypartitionhere failed

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https://bugs.launchpad.net/bugs/927828

Title:
  sudo: pam_mount.c:417: modify_pm_count: Assertion `user != ((void
  *)0)' failed.

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