I ran into this as well.  update manager did not notice the prompt (it
was only visible in the "Terminal" output).  In the past, we'd altered
openssl's prompting levels to auto-restart when running within update-
manager.  Perhaps that patch was accidentally dropped?

** Changed in: openssl (Ubuntu)
   Importance: Undecided => Medium
       Status: New => Confirmed
       Target: None => ubuntu-8.04

** Summary changed:

- libssl asks for user input during Gutsy->Hardy
+ openssl asks for user input during Gutsy->Hardy

-- 
openssl asks for user input during Gutsy->Hardy
https://bugs.launchpad.net/bugs/182446
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