Randomly. Don't wait for any signal, because chances are, your dream won't give you a signal. If you have to write notes to yourself reminding you to do a reality check, scrap them after a while because there won't be notes in your dreams. Basically, be skeptical about your surroundings. Observe things more often, and a few times a day, really stop and ask yourself if you're dreaming, then do a reality check.
When you're dreaming, you do things without thinking "why am I doing this?" Instead, you should ask yourself that. The way it works is if you're skeptical enough in real life, it'll pass over into your dreams.
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