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Oil/Silk Cigar

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Does the silkiness or oilyness of the wrapper go away with time or increase with time?
 
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If well cared for, oil should go away slowly. It won't ever increase. Most of us favor 70 degrees and 60-65%RH.

Silkyness I would say refers more to how soft and vein-free the wrapper is. Veins won't change. But in my experience a good deal of age increases smoothness somewhat. The wrapper is fermenting over time, so as long as it does not dry out it should become somewhat more supple.

VERY old cigars (10+ years) I have limited experience with, but it would be hard to imagine them not eventually losing the soft "give" they initially have. If moisture stays present, organic materials can last a very long time without becoming brittle. But those oils are key. Once they go, the cigar won't be the same.
 
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How big a difference does Temperature make? My cooler and humidor hold steady between 65 and 67. But the temp fluctuates between 60 and 70. Should I be concerned?
 
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Temp wise, you're in a great range. I wouldn't worry about 60 to 70 unless it changes very fast. Over the course of a day, you're ok. Steadier is always better.

Temps under 60, you could lose oils faster. And your humidity will drop as well. In the summer, when my wineador is turned on, it's pegged at 66. In the winter it fluctuates with room temp. Ideally I'd keep it at 70, but 66 is as high as it goes, and I have not installed additional equipment to change that (though many handy guys here do).

The real danger with temperature is anything over 75. If tobacco beetles are present in the cigars, they can hatch in that heat, and you have a big problem.
 
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