The series info is not sent on the initial connection. It's a chicken and egg issue.
The calibre driver has to update the database on the Kobo to add in the series info, but when a book is transferred (ie the initial connection) the required row is not yet in the database.
The row is only added when, after the Kobo is disconnected, the Kobo processes the new book.
When the Kobo is reconnected to calibre the driver can now update the database on the Kobo with the series info
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