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To give some additional info I found here: http://help.octopusdeploy.com/discussions/questions/9660-rolling-deployments-target-order

quoted text:
> The answer is: the order is undefined. We retrieve the machines from the SQL Server database without specifying an order (so SQL Server will just return them in whatever order will be fastest). There is currently no way to specify the order for a rolling deployment.

It would be nice if, at least, that SQL result was alphabetically ordered to have the chance to predetermine the targets deployment order.