Firstly, it is always a good idea to state the actual versions of software involved. And report any extras, in this case the plugins, being used. Sometimes we will know immediately what the problem is.
In this case, the most likely reason for this to be happening is that you installed calibre 5.1 and have been using the KoboTouchExtended driver and are a Windows user. There was a problem in the Python libraries that calibre has been using that occasionally would mean this and some other plugins would not load. With calibre 5.1, it went from "occasionally" to "always". This would then mean that calibre would be using the built-in KoboTouch driver when communicating with a Kobo device. And it was probably configured differently to the KoboTouchExtended driver and didn't update the series info.
If that is not it, then you should check the configuration of the driver. Make sure the metadata update option is on and either the series option or the Update metadata option (this includes series updates). Then make sure the metadata management option of the "Sending books to devices" page of the preferences is set to the automatic option. That will do the updates each time you connect the device.
If that isn't it, then we need more detail. A debug log would probably show what is happening.
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