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When using the Firefox extension, are the settings and custom styles backed up so that when I restore my Firefox to another machine I'll still have all my settings?
If not, how to enable it?
You can't really trust Firefox Sync to handle add-on data reliably (assuming you set up Firefox Sync). You probably should make a file backup of your critical data. See:
Within Stylish, on the Manage All Styles page, you can use the "Backup all Installed" button to create a backup file. Stylish is no longer available to install from the Add-ons site (it was taken down). You could consider installing Stylus on the new machine. This article has more on import/export:
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