I can reproduce exactly Simon's behaviour.
Added gksu here and set update-manager to invalid.

** Also affects: gksu (Ubuntu)
   Importance: Undecided
       Status: New

** Changed in: update-manager (Ubuntu)
       Status: New => Invalid

** Summary changed:

- update manager should show invalid sudo password warning
+ gksu does not repeat password prompt if wrong password

** Description changed:

+ gksu only asks once for the password and then gives up if a wrong password is 
given.
+ It should ask 3 times (and then possibly complain to the user in a dialog?)
+ 
+ === Original report: ===
+ 
  To the wishlist:
  
  Open update-manager, check for packages to install and click on
  "install". It'll ask for your password, if you get it wrong it won't
  tell you. It just refreshes the package listing and show the update
  manager window again.
  
  I'm running the latest Ubuntu with all updates applied, but it's an
  issue for a long time, really. It's not critical but it's a big of a
  nuisance, since I always do multiple things at the same time and I can
  easily forget to check the update window for hours or even days.
  
  A simple dialog would be fine, but sudo insults (if enable) would be
  much better. ;)
  
  cheers!

** Description changed:

  gksu only asks once for the password and then gives up if a wrong password is 
given.
  It should ask 3 times (and then possibly complain to the user in a dialog?)
+ 
+ See comment #4 how to reproduce.
  
  === Original report: ===
  
  To the wishlist:
  
  Open update-manager, check for packages to install and click on
  "install". It'll ask for your password, if you get it wrong it won't
  tell you. It just refreshes the package listing and show the update
  manager window again.
  
  I'm running the latest Ubuntu with all updates applied, but it's an
  issue for a long time, really. It's not critical but it's a big of a
  nuisance, since I always do multiple things at the same time and I can
  easily forget to check the update window for hours or even days.
  
  A simple dialog would be fine, but sudo insults (if enable) would be
  much better. ;)
  
  cheers!

** Tags added: apport-collected

-- 
gksu does not repeat password prompt if wrong password
https://bugs.launchpad.net/bugs/338151
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