Thanks for this how-to 
If we’re using discourse with 2 containers (web + data), when should we need to rebuild the data one?
When there’s a postgres or redis update. They are pretty unusual (on the order of once a year or less), but keeping up with that I guess is a reason people think it’s complicated.
And usually even if you wait a long time after an upgrade things will still work with the older version. Or sometimes, they’ll add something to the database and your won’t need it unless you’re using the AI plugin.
The Literate Computing Dashboard will do those when they are necessary
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