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Leaky iron roof - hard to diagnose

Somewhere there's a leak, it's apparent during heavy rain. Might relate to the angle of the rain/wind. It's near the kitchen window in an extension area of the house. I know it doesn't originate further up because the original part of the house has roof access via manwhole and it's all dry. I siliconed a few nails that looked off, but it didn't fix the issue. I work from home so very flexible: can come and check it out whenever you like.