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When adding the .txt files via the GUI then Calibre will not automatically pick up the associated .jpg files. They would have to be added manually afterwards. This would involve getting a particular book to be selected in the main winow, and then you could drag-and-drop or copy-paste the cover image to replace the one currently showing.
Alternatively if you are up to it, you could write a script to add the files using the Calibre command line tools. Doing it that way would also allow you to add the covers at the same time, but it does require you have to the skills to produce such a script.
What is your final target format? A book cover cannot be embedded in a txt file, so I am assuming that you are likely to want to convert to some other format that DOES support embedded covers such as EPUB or MOBI? As long as you have added the cover in calibre, then if you run a conversion from .txt to the target format Calibre can automatically embed the cover for you.
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