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[xenial] Test upgrade path: Ubuntu 14.04.5 → 14.04.5 with all updates → 16.04 #3965

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@eloquence

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@eloquence

Our plan of record is to upgrade from Ubuntu 14.04 to Ubuntu 16.04 by first ensuring that the system is updated to all latest packages available for Ubuntu 14.04 (not just security updates).

This is because the package version state of a SecureDrop server partially depends on whether or not the administrator has run the Ansible playbook, which causes a full package update.

To ensure that this strategy is viable, we should test the following upgrade path:

  1. Install from a 14.04.5 base image.
  2. Run apt-get update && apt-get upgrade
  3. Run do-release-upgrade

Beyond looking for showstopper bugs, we will want to compare the final system state with an install from a 16.04 base image to ensure that this upgrade does not result in odd inconsistencies that could cause problems later. This research may generate more tickets.

Part of #3204.

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