I remember in older trellis versions (before the bento box was used), you were prompted for a box update quite frequently. Now the version seems to be pinned at 2.2.9 while the latest version is 2.3.7. Wouldn’t a box update make sense to be closer to the versions you get at your host?
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Probably 
Would you like to test the new version and do a PR with the change?
Sure, will do. Would creating a new box and a box update with an existing box be enough testing?
Hm, apparently you can’t simply set vagrant_box_version: '2.3.7' in vagrant.default.yml.
Running vagrant box update gives you: Box 'bento/ubuntu-16.04' not installed, can't check for updates. then (for an existing box, that is). Probably because it looks for 2.3.7 which isn’t installed.
Maybe we could use vagrant_box_version: '<= 2.3.7', where the version number could be lifted then. Would that be OK?
OTOH the vm has to be destroyed and rebuilt to reflect the box changes anyway…
Yeah that’s definitely needed. '<= 2.3.7' seems fine to me. The process to update is manual anyway.