I have reproduced the issue on the latest CLI version.
Yes, I am on the latest version
I have searched existing posts and this report is not a duplicate.
Yes, this isn’t a duplicate
In which of these areas are you experiencing a problem?
Theme
Expected behavior
When running shopify theme dev, remote files should be updated when changes are made to local files
Actual behavior
In some cases local files are changed but CLI does not detect the change and does not upload the new file.
Reproduction steps
Not sure exactly but I’ve noticed it happening in a consistent pattern. I have a variety of custom theme builds that all use a similar build pipeline that compiles styles from, for example a product.scss entrypoint, which imports a _product-form.scss partial, and outputs a assets/product.min.css file.
I have a watch process running and when I save the _product-form.scss it automatically recompiles and updates the assets/product.min.css file. This change is picked up by the CLI and updated as expected.
Eventually, as far as I can tell when the product reaches a certain complexity (number of asset files?), this same change does not get picked up. I save the partial _product-form.scss, my build process runs, the assets/product.min.css does get updated as expected, but the CLI doesn’t notice. If I open the asset and save without making any changes the CLI does notice and upload.
Strangely, if I update and save the product.scss entry point, the asset/product.min.css change is reliably picked up by the CLI.
Seems like there must be some difference in how my build process handles these cases but regardless, presumably the CLI should pick up the change either way - I should never have a case when my local files do not match the remote theme.
Verbose output
Verbose output is too long for this forum…
It shows nothing when this issue occurs - when it is supposed to pick up on the update and upload nothing is indicated in the output.
If there is specific (shorter) content from the output that would help debug I can provide.
Operating system
MacOS 26.2
CLI version
3.90.0
Shell
zsh
Nodejs version
24.0.1