Given the cascading nature of CSS, determining the correct import order for Sass files is a problem. If you automatically import all files in a directory you have no way to control which files go first. Thus it becomes impossible to confidently override Sass written in another file.
Even if there were some kind of guideline (like alphabetical order) you'll have to resort to unconventional naming rules, which isn't very discoverable.
It seems like a nice feature and many have suggested it, but there are too many oddities for it to be practical, and in the end only saves you from typing out filenames but then creates complexities in places where there were none before.
- Brandon Mathis
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