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Message: <blockquote data-quote="iserith" data-source="post: 6740650" data-attributes="member: 97077">The intention seems to be that the caster cannot teleport into an occupied space. However, given the size of the creature, there are plenty of unoccupied spaces around it. Therefore, I'd say it's fine as long as the person manages to hold on to the creature they're now riding with a free hand or some other means. This potentially means not using a two-handed weapon or a shield.If the character has a free hand on the creature, I wouldn't say so. If the players want to have the character ride the monster like a surfboard, however, perhaps because they want to use a two-handed weapon for more damage, then the player must consider the trade-off: On the dragon's turn, it can wing over during its movement, forcing a DC 15 Dexterity saving throw to avoid falling. The DC, of course, can be higher or lower, depending on the circumstances, or the character could have advantage or disadvantage.I wouldn't have called for the saving throw to hang on in that particular case. If you're going to change the way you rule on a substantially similar situation in the future, it's a good idea to let the players know. Consistency as to the DM's rulings are an important part of players making informed decisions.In any case, it sounds like you had fun and created an exciting, memorable story, so I wouldn't go looking for problems where there apparently are none.</blockquote>