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Message: <blockquote data-quote="Zander" data-source="post: 6550450" data-attributes="member: 1364">The dragon could still use its legendary action to fly free. It would just need to hold back on using its legendary actions. It's exactly like the wizard rolling a low initiative. The same outcome can occur in the RAW, it's just a change in probability.If a DM allows PCs to deliberately lose initiative, the DM can do it too. If for whatever reason the monster(s) wanted to come last in an encounter where the PCs all acted on their rolled initiative, that would be OK. What's sauce for the goose...    Yes, it could be used every encounter but in your scenario #1, the wizard probably wouldn't want to. My DM - and I think most DMs - doesn't allow Help to linger. It only grants advantage while it is being provided. So a familiar couldn't fly in, Help and fly out and then grant advantage to the wizard acting later in the round. To grant advantage, the familiar would need to stay close to the opponent after Helping which opens it up to melee attacks from the opponent. Also, in your scenario #1, the Help might go to a PC attacking the opponent who acted before the wizard (unless the familiar readied Help) - another reason the wizard might not want to do it.</blockquote>