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The setting takes place in medieval times (around the 10th-13th century)

Say an important person of court is visiting a king of another nation. He is there as an ally, but needs to sneak out of the castle during the day (the weather is rainy). The castle has an a keep and a gatehouse. Would this important person be questioned on his way out of the castle? Can he just go out undetected? Or would guards question him? If it would be hard for him to go out the front gates, how else could he leave the castle and venture into the city?

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closed as off-topic by Renan, Cyn, rek, Mołot, Rekesoft Mar 14 at 10:47

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    $\begingroup$ This question seems extremely broad. The answer depends on what blind spots the keep windows have, the skill of the sneaker, the morale and integrity of the guards, the terrain immediately surrounding the castle, the physical attributes of the sneaker, what disguises and clothes he can avail himself of, and what paranoia rating the king is currently on. I doubt anyone could give a perfect yes or no to this. $\endgroup$ – Tim B II Mar 13 at 23:20
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    $\begingroup$ Since he's probably on his way to purchase sex at a local bordello (along with many others from the castle), why bother to be sneaky about it? He should be proud of his size and prowess, and ensure every guard knows that he's wealthy and powerful enough to have such a great hobby. If he is in the unusual circumstance of going someplace else, simply lie and say he's off to the bordello once more. $\endgroup$ – user535733 Mar 13 at 23:20
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    $\begingroup$ does your castle have any postern? $\endgroup$ – Kepotx Mar 13 at 23:39
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    $\begingroup$ Corpses do not get interrogated. $\endgroup$ – kikirex Mar 13 at 23:57
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    $\begingroup$ Kings did not live in castles, except occasionally in war time. Castles were military structures, nobody lived in them unless they were paid, or if they had to due to military obligations. Kings lived in palaces. Palaces have lots of doors, many people coming and going all day long. $\endgroup$ – AlexP Mar 14 at 7:36
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That very much depends on the situation. The castle, the threat level, the size and location, etc.

It's certainly plausible that they could do so in some castles some of the time. A large castle would have people entering and leaving all the time including servants and soldiers working for the visitor who the guards would not recognize.

Coming back in is likely to be more difficult (after all castles are designed to keep people out not in) but you have to remember that goods and people were constantly flowing into and out of castles. The visitor could dress as one of their own guards or servants and just walk out and back in on some errand or other so long as the guards didn't recognize them.

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    $\begingroup$ I am going with the servant approach, as in, he is going to wear common cloths and walk near the servants on their way out. Thanks! $\endgroup$ – Ebi Mar 13 at 23:55
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The answer is in your own text:

an important person of court is visiting a king of another nation

Visitors, especially high ranked ones like kings, are guests and free to move as they please, and often move together with a large escorting party. Those who are restricted in their freedom of movement are called prisoners or hostages.

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As Tim B said, this depends a lot on the situation

I would add that armies were only mobilized during wartime. Having a full-time levy cost a ton of money, and would not be used to guard a castle if they were no danger.

In September 1238, Henry III, his queen Eleanor, and their retinue were at Woodstock. A man pretending to be insane had thrown himself at Henry, demanding that Henry give his crown to him. Henry, believing he was a madman, restrained his servants from beating or killing the man. That night, however, the same man climbed through a window into the king's bedchamber, armed with a knife. He meant to stab Henry in his bed, but Henry was in the queen's chambers with Eleanor. One of the queen's damsels, Margaret Biset, was reciting her psalter and heard the man. She alerted the guards, who captured and tortured the intruder, who confessed that William de Marisco had sent him to murder the king and queen.

https://plantagenesta.livejournal.com/63308.html

This is a historical example that can show that sneaking into a castle, and even in king's chamber was possible.

Also, a postern could help you to sneak out of the castle. They were used as a hidden, easily defendable passage. Your character can have some trouble finding it if he doesn't know the castle, and it may be locked, as common folk just enter/leave by the gatehouse, but it worth to try.

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