City states become wary

...you still won't be able to get tribute because IIRC it doesn't seem to work when in the red

That is correct. So you have to be careful moving units. They have to be on the border but not in the CS territory. That bit I understand -- but I still cannot make GD work. But I don't do much early tribute demands, and that would be good practice for GD, because the game mechanic is identical (so far as I understand).
 
Demanding a tribute makes it harder for the CS to fear you. It will give it something like 200 points which need to be surpassed by points generated by your military power (overall military power + military near the CS). This is decreased over time, until it is completely gone.

Other factors that give points to CS, and make it harder for the CS to fear you are: having negative influence, CS personality (a Hostile CS will have extra points), having a pledge of protection, and having an ally (I'm not sure about this one).

You can hover over the Demand screen and all information is displayed. With gunboat diplomacy you get a 50% bonus to your military power so it will be easier. If you are not influencing the CS, most of the times bringing around a couple more strong units is enough. Unless you are Greece, you need to be careful not to stay in CS territory (at least until you become friends), and also removing a pledge of protection will help.
 
In addition to what claudiupb mentioned, CSs with higher combat strength (on a hill/built walls...) are harder to demand tribute from. I think them having more units also increases the difficulty of tributing.
 
Please do share if you find that it is not all of them!



I have never been able to get much out of Gunboat Diplomacy. I thought there were other caveats, like that your military had to be #1 or #2? Late game, I could spare an XCOM if it really that easy...

I will need to do this again and take a screenshot of what I thought I saw, I could very well be wrong.

As for the demanding tribute penalty, Tribute does go up ridiculously after demanding, which is why its good to not demand tribute ten turns prior to getting Gunboats as it takes that long for the penalty to disappear from what I have found. The reason XCOM's are good is because they are so mobile, you can launch them from anywhere on the map and they are right there next to the city state next turn immediately beginning the influence build if your overall military power plus 50% bonus is strong enough. I still don't know how military might is calculated, but 10-15 XCOMS combined with whatever else is hanging around your empire should be more than enough to demand tribute from city states. 100 hit points per XCOM doesn't hurt either I am sure, especially with the proximity multiplier.
 
Please do share if you find that it is not all of them!

It's not all of them, but I am unable to find a correlation to what's going on.

I accidentally DoW'd Kabul in my last game, after stealing a worker from Zurich. Kabul went to wary immediately, -20 resting point, and -2 per turn. All of the other city states went to either -2 per turn or -1.5 per turn, but none of them had the -20 resting point. I don't know why some were -2 and some were -1.5 though. It may have been CS's i met after the DoW with Kabul, but I can't say for certain.
 
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