This mainly seems like a UI sync issue. After waiting for while it usually refreshes with the missing reason for upgrade in red.
I see from the lookout tower window you have the resources to upgrade, but do you have enough resources when you check the resources window? I wonder if one of the windows is incorrectly reporting resources.
When the window popped up I was definitely missing iron. But the UI didn’t reflect it right from the go. Waiting for a while does appear to update the UI accordingly.
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