Generally we farmers wait until it is obvious something needs attention - might as well wait until your sickle is obviously dull. Is your sickle top-serated, bottom-serated, or smooth? The smooth you can sharpen for a long time, and these are the common type if you are set for hay. Bottom-serated can also be sharpened for a while. The top serated sickles don't really sharpen well - you end up turning them into smooth, but doesn't take too well. THE best way is to remove the sickle, and sharpen on a slowmoving waterstone. Will make a very fine edge again, and keep the sickles cool, will not harm the temper. However, only us old farm coots have one of those in the shop. I've heard of the 'v' sharpening wheels, do they fit on a drill or angle grinder or are hand powered? Sound good whatever they are. I've used an angle grinder often enough, works well, but go light & keep it moving. If you heat the sickle, it will wear out quick & never keep an edge. Pay attention to the ledger plates too as the other person said. Some are serated, some are smooth, but they should have a nice sharp edge, not rounded over. --->Paul
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