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If a lord is captured and imprisoned in a city, I have the option of attempting to rescue them. These missions are very difficult so I'm curious, will they ever escape on their own? If so, is the chance of escape the same as enemy lords who I have imprisoned?

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Yes your own lords will escape on their own. If I remember correctly their likelihood of escape is dependant on the number of troops in the garrison and whether the castle/town has a prisoner tower constructed.

It can take a while for a lord to escape so you might want to rescue them yourself. You also get a significant relationship bonus with them and also with their family members. You can often get a quest to rescue them if you talk to their mother/sisters/daughter. This can be useful to raise your relation when courting a potential suitor. The rescue shouldn't be that hard. The defenders are spread out so you usually only have to fight a few at a time.

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