Hi...
Normally to upgrade an outpost I simply move a pioneer onto it and select the upgrade option... but I have a strange case where a dwarf form a friendly faction is sitting IN my outpost.
- If I mouse over it with the Pioneer selected I only get the "speech bubble".
- If I click on the outpost I get the dwarf
- If I click a second time on the outpost the outpost itself is selected.
Here is the dwarf selected... (of you have the pioner selected it is a speech button and brings up the diplomatic chat)

As I said if I click (with out the pioneer selected it selected the Dwarf... but if I click a second time it select the outpost proper.

Any idea what do to there?