You'll have to write a /bug report for SOE. There are a couple strange things and bugs with the chat windows.
I use two chat windows and "Always chat here" seems to always reset to my second chat window when I log off. I've just left it there now.
When you click on the icon for an item in an examine window it pastes the item link into your first ever chat window, ignoring "Always chat here". If for some reason you've closed your first ever chat window you won't see the item link. The same is true if you use the "link to guild" button in the cloak design window.
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