I can't get the option to upgrade the item given to me by the rogue.
I'm high enough level and I have the item (ruby). Any help out there?
Thanks

Your henchman should "finish" his story, it is usually written then in the journas as such too. Then initiate the dialogue with him/her again and say, that you just want to speak with them. Ask about their story again and it should then provide you the option to turn in the item they seek, thus upgrading the old item. If not, check what the Journal says about the henchman.

Are you sure you have the right item? Tomi doesn't want a ruby, he wants the Star of Calimsham. It's a specific item, found in Wanev's tower off of the South Road.

I finished with the complete story with tomi. It said maybe we will find that ruby someday...(star of cashman sp?) Yet, I've found it but now when I talk to tomi it just lets me ask him about my quest.