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Clara BW When does Kobo update KoboReader.sqlite database for highlighte?

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I have built a server that accepts Kobo's sqlite database and syncs highlights and notes to Notion. I have also set up NickelMenu and added an item that uploads the sqlite db to the my server. The communication works fine and I can see my highlights and notes in Notion.

However, I am facing an odd issue with the database itself. When I add a highlight or a note, the database does not get the data. The behavior is very weird. Sometimes it updates when I plug the usb cable, sometimes it updates when click the Sync button but there is no consistency about all highlights being there. Has anyone faced this? Is there a way that I can force Kobo to write the data into the database? Or have I possibly misconfigured something here?

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