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Adonnus

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Apr 17, 2011
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Even on the easiest difficulty I can't win any sieges with relatively even sized forces. I have better in general units than my enemy but when they go up the ladder to attack they get pounded along the way by archers and can't get a foothold on the walls before getting slaughtered at the ladder exit by spearmen.
 
You won't win battles with even sized forces unless you do a thing like this:

You don't need 700 troops to take a town. In fact, I managed to take 2 towns and 3 castles with a troop limit between 120 and 130 using only my own troops. The key to this is:

1. Have only elite troops while attacking fortresses. Hopefully you and your companions have high training skills - with them, you can turn a large bunch of peasants into elite troops just by training in one week.

2. Do not try to kill all defenders in one battle - wear them down instead. Start the siege with 100 Rhodok Sharpshooters, order them to hold their position immediately, and see how they kill enemies in much larger numbers than they suffer losses themself. Having a good medic with high surgery helps too, so many of your losses will be only temporary.
Once your troops stop firing due to the lack of ammunition, retreat from the battle and start to build new ladders/a siegetower directly afterwards. After several battles, the garrison is defeated.
Should your archers be inefficient as the enemy has only infantry left with strong shields, so that they barely kill someone, retreat to your nearest castle/city, swap your archers with powerful melee fighters like Huscarls and start an assault in the next siege attempt.
Obviously, this works much better if you only have to build ladders as you don't have to wait as long as with siege towers.

Otherwise if it's just a matter of numbers and you are a vassal of one of the kingdoms, you can ask a fellow lord to join you (May i suggest a coarse of action -> will you follow me, i have a plan). This way you outnumber the defenders and you increase the change of winning.

I believe the difficulty settings has nothing to do when assaulting a town or castle. Only you and the heroes you hire get reduced damage, but even then when you face 6 opponents and a lot of ranged units from the side, you get knocked out fast. Instead of being 1 shotted, it might take a few hits, but you won't be able to solo a enemy castle or town.

There is however 1 castle i know of that used to have the front gate open when under siege. Although the assaulting troops won't ever go through it and always take the ladders(even when following you), you on the other hand can go past it and attack the defenders from the rear. You can also have your archers hold position while you get the attention of the defenders and when they face you, you order your men to start shooting the enemy in the back. I think it was a swabian castle along the Nord/Veagirs border, but maybe it got fixed, because it was quite a while ago when i found this out.