Mark,

Why not present the upgrade option in the three situations? At login, at
log out/shutdown and during the session (only once per session or per
day or whatever is a reasonable time)? This would be a away to encourage
upgrades. The key here is to make updates at each moment optional. So
that they do not disrupt the user work flow unless he/she accepts it.

If the user decides to update at login or during a session the system
should tell him when the update needs a restart and prompt the user if
he/she wants to continue.

best,

Paulo



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