The pencil tool is not working correctly

I've been making my drawing with the pencil tool obviously. After I make a stroke, I continue it with the last anchor point. But sometimes when I do that, the previous stroke disappears completley. Why is that?

That's because Illustrator has got a pretty lame understanding about what should happen when you continue a path in certain angles while the Modify selected paths option is turned on inside the Pencil Tool options.
You can disable that option but I can imagine that this is not what you're really looking for.

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