Originally Posted by dsvick
With that being said though as far as I know the only way to get books to remain in a certain order is to use the Sony software.
Calibre handles sending Series to your reader in order just fine.
In order for my series to show up in order on my Sony reader I have to do a few things.
1. Remove any books in the series from the reader.
2. Sort the series in the Calibre library by clicking on the series column once the series is in order move on to the next step.
3. Now that the series is in order in the Calibre library, select all the books in the series.
4. Click send to device.
This will send the entire series to your device at one time and they will be in series order on your device.
If later you add a newer book to the series you can send it to the device by itself and it will just be added to the end of the series.
This works every time.