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Yarp!
As the pins and rollers wear the effective length of each link increases, so each roller is picked-up higher on the tooth and then slides down as the sprocket rotates: hence the characteristic "shark's tooth/wave" shape of worn teeth.
One of these is best, as it only measures the wear at one roller/pin, whereas the more common type measure it at two and will have you changing your chain too early.
But that's better than too late...
Is this chains inability to seat itself an indicator that it's time to replace it?