I'm seeing this, too.  The system in question was upgraded from an
earlier version of ubuntu to 9.04.

Update Manager says "Your system is up to date.  The package
information was last updated 25 days ago."  (!)

$ ls -l /var/lib/apt/periodic
total 0
-rw-r--r-- 1 root root 0 2009-04-22 19:53 update-stamp
-rw-r--r-- 1 root root 0 2009-05-18 09:08 update-success-stamp

$ ls -l /etc/cron.daily/apt
-rw-r--r-- 1 root root 8686 2009-04-16 21:27 /etc/cron.daily/apt

That seems like a bug.  How the heck did that not get set to mode 755?

For completeness:

Software Sources shows it checks for updates daily and has jaunty-
updates and security checked.

$ ps ax|grep update-notifier
 3671 ?        S      0:00 update-notifier --startup-delay=60
 5990 pts/2    S+     0:00 grep update-notifier
$ killall update-notifier ; update-notifier --debug-updates
(update-notifier:5993): update-DEBUG: update_check()

** (update-notifier:5993): DEBUG: /usr/lib/update-notifier/apt-check returned 0 
(security: 0)
** (update-notifier:5993): DEBUG: crashreport_check

[then sits there forever]

$ last dank
dank     tty7         :0               Fri Jun 12 10:13   still logged in   
dank     tty7         :0               Sun Jun  7 17:02 - down   (00:56)    
dank     tty7         :0               Sun Jun  7 07:04 - down   (01:58)    
dank     tty7         :0               Sat Jun  6 19:26 - down   (00:18)    
dank     tty7         :0               Wed Jun  3 03:05 - down   (02:04)    
dank     tty7         :0               Tue Jun  2 07:58 - down   (04:20)    
dank     tty7         :0               Tue Jun  2 03:58 - down   (00:43)    
wtmp begins Mon Jun  1 19:53:23 2009

$ ls -l /etc/issue
-rw-r--r-- 1 root root 19 2009-04-13 02:33 /etc/issue
$ cat /etc/issue
Ubuntu 9.04 \n \l
$ ls -l /var/log/dpkg*
-rw-r----- 1 root adm      0 2009-06-01 17:56 /var/log/dpkg.log
-rw-r----- 1 root adm 160998 2009-05-27 10:32 /var/log/dpkg.log.1
-rw-r----- 1 root adm  86844 2009-04-23 20:24 /var/log/dpkg.log.2.gz
-rw-r----- 1 root adm   9454 2009-04-15 19:42 /var/log/dpkg.log.3.gz

-- 
update-manager doesn't show updates, even after 1 week
https://bugs.launchpad.net/bugs/356152
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