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Winding or Setting Slips in a Pocketwatch
If all this is working well, fine, if not then the watch may not securely engage at one side or the other and may "skip" or "pop" as it winds and sets as the gear teeth slip. This is bad because the gear teeth will be being exposed to unusual wear and stress, and will fail before long.
Often the parts that slide the clutch themselves wear at the points they push on other parts. This is the case with this watch, and when that happens the mechanism ends up not pushing some part far enough, and the gears end up not fully engaged.
These are very hard parts to replace with new... But the long springs that push on these parts are usually secured with a screw, and when that is loose, it is possible to turn the spring just a little so that it will push more, or less. By doing this, over and over, and adjusting the depth of the stem in the watch case, it is sometimes possible to split the difference and get the watch both winding and setting.
The engagement is not 100%, but a very slight push inward on the crown, witch is natural when winding anyway, seems to hold it enough to engage the beveled pinion and start winding. Once there is a turn's worth of power, the mainspring tension is enough to hold the clutch and it feels fine.
The watch is a Hamilton 947 16 size pocketwatch. A winding/setting mechanism like this is very common in American watches.
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