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I can't figure out how to get the LESS files in my theme to update. I've tried every different .less file the docs recommend. I've tried copying this file from samples:

https://github.com/magento/magento2-samples/blob/master/sample-module-theme/web/css/source/_theme.less

to the same exact spot in my own theme (/app/design/frontend/Grant/knit/web/css/source). I'm running in dev mode, clearing the cache, and forcing static deploy (even though I shouldn't have to), and I can't get the changes to register.

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You need to use _extend.less instead _theme.less then flush cache and use

php bin/magento setup:static-content:deploy

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