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I use DW CS6. When I go to insert an image for the first time (meaning, it's the first time anything was opened in that folder), it always shows the wrong folder. Before, it opened the folder where the html file is in, which should be the default. I'm not sure whether that happens with DW CC as well, but CC is not an option. Will I be stuck with that behavior because CS doesn't get updated anymore? My work requires me to have jobs in job folders, so I code several html files a day and every new job has that happening. It's not only annoying, but productivity suffers. Does anyone know a solution?
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As with any tool, there are a number of rules to follow, the main one when using Dreamweaver is that you must define your site as per Project overview and site setup | and go down to 'Set up a site in Dreamweaver'.
When you go to Local Info, you can set the Default Images folder.
In case I have not read your problem correctly, please explain a bit better.
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I'm almost sure DW's behavior was not that before installing High-Sierra -- it would use the folder of the html I was working on as the default when inserting images, without defining sites, as I'm using the "relative to: Document" setting. So, with the images saved in the same folder, it would immediately show its contents without the need to browse and find the folder, which is what it's doing now.