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The Elder Scrolls IV: Oblivion Hints
How can I get the guard to let me in?
1 of 6: Wait until after 6 pm to talk to him about it.
2 of 6: You can then get in if you're dressed well enough.
3 of 6: That means if the clothing you're wearing is valuable-looking enough.
4 of 6: Expensive magic items will definitely do the trick.
5 of 6: NOTE: Even if you have very valuable magic jewelry equipped, that may not work if you're not wearing any regular clothing. If this is the case, go get some clothing items from a guild building or home, and wear them long enough to get past the guard.
6 of 6: Otherwise, you can get the guard's disposition up to 70 via bribes or the persuasion mini-game to get him to let you in.