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The send to template should be modified. It is storing books in the root directory of your Kobo which has limited directory entries. I would suggest just copying my template so the books are stored in a subdirectory called eBooks with the file and directory names kept shorter (the default template uses all the author names in both the directory name and filename which can easily lead to overly long paths.
At this point, you don't need to worry about the rest of my customization.
If you have Kobo Utilities installed, just select Configure driver from the menu. Otherwise, you will have to go into Preferences => Advanced => Plugins and find the KoboTouch driver and then click on Customize plugin. Copy/paste the template and then restart calibre.
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