Of the three growth paths available for Jerry, Ashton liked the idea of him being a Task Manager.
Based on what he read from the System's description, Task Managers are linked to the System, they do possess some form of individuality but ultimately they are extremely loyal to the System's Host, which is him of course.
Don't misunderstand, Ashton isn't doubting Jerry's loyalty. The little helper has been with him through thick and thin so there's not even a shadow of doubt in his mind about Jerry's loyalty.
Ashton just thinks it's best that Jerry was to be linked with the System. Who knows what possibilities may occur if this was to happen?
But of course, changing Jerry wouldn't be so simple. Before he could even consider making him a Task Manager, Ashton has to upgrade everything about Jerry first.
Looking at the System's Prompt in front of him, he could see the list of materials needed for Jerry's upgrade.