Backup order after "missed" time schedule

Does this really mean that several permanently-daily-scheduled jobs run after cron start, however system downtime causes missed schedules, and some missed jobs get in first?

was an earlier theory, however it’s not certain. So you’re sure yours is looking random?

They are not mutually exclusive. Duplicati 2.0 could start GUI jobs from CLI using:

A command line client for controlling the Duplicati Server (third party contribution)

ServerUtil is for Duplicati 2.1, and has more in it than the documentation mentions:

Commands:
  pause <duration>                Pauses the server []
  resume                          Resumes the server
  list-backups                    List all backups
  run <backup>                    Runs a backup
  login                           Logs in to the server
  change-password <new-password>  Changes the server password
  logout                          Logs out of the server
  import <file> <passphrase>      Import a backup configuration
  export <backups>                Export a backup configuration
  health                          Checks the server health endpoint
  issue-forever-token             Issues a long-lived access token
  status                          Gets the server status

One approach (if the “missed” run order is truly random – which maybe dev can resolve) would be to have cron start Duplicati as current, and either run the first backup or let it be permanently scheduled. First job has run-script-after to run the second, etc. Force chain.