The window sounds like the logical problem. After you remove all of the old caulk and clean the area with the proper solvent use Dicor non-self leveling caulk. It will last much longer than silicone caulk. While you're at it give the roof a very thorough examination. I resealed my roof two years ago and used the Dicor two part roof sealant and it still looks great. While windows and doors can leak the biggest source of water intrusion is the roof and all of the penetrations on it. Good luck!
RichH
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