Do you take damage from falling while wearing Winged Boots?

Question

In 4th Edition the magic item clearly stated that you dont take damage and that you land on your feet while wearing them, but in 5e there is no such language in the description. The description of Winged Boots reads:

While you wear these boots, you have a flying speed equal to your walking speed. You can use the boots to fly for up to 4 hours, all at once or in several shorter flights, each using a minimum of 1 minute from the duration. If you are flying when the duration expires, you descend at a rate of 30ft per round until you land. the boots regain 2 hours of flying capability for every 12 hours they aren't in use. (DMG p.214)

The question here is would they take falling damage from the height they start their fall from, would they only take the last 30 feet in falling damage, or would they take no falling damage?

Answer 1

While it's not spelled out explicitly that you take no damage, the intention seems to be that you take no damage.

You fall 30ft per round, which is about 5ft per second, which is much too slow to be taking falling damage. (Even slower than Feather Fall, which is 60ft/round)

Keep in mind that you're descending at a regular walking pace, and you are free to land on your feet at the end.

Do keep in mind that the "slow fall" feature only works while you are using the flying option of the boots. If you just drop off a cliff without flying, the boots will not protect you.

Answer 2

It's important to note, Winged Boots grant you a flying speed, which is used during your movement.

If you weren't flying when the fall occurs, it largely depends on who's turn it is. If you were exploring and hit a covered pit trap outside of combat, since you were walking when it happened, you could make the case for using your fly speed since you were Moving.

If you walked into a pit trap on your turn in combat, you can use your fly speed as part of your movement, provided you haven't used all your speed.

However, if during combat an enemy throws you over a ledge and you weren't flying to begin with, you won't be able to use your movement until your turn to take advantage of the Fly speed. Or, rather, by the time your turn comes up, you will have already hit the ground.

Jeremy Crawford makes the same case in a tweet:

Winged boots give a flying speed. You can use that speed to move. The boots don't auto-activate to prevent a fall if you're on foot.

If the fall was sufficiently far enough that you were afforded movement, then you could fly to prevent "falling".

Optional rules on the rate of falling are described in Xanathar's Guide to Everything (p. 77)

The rule for falling assumes that a creature immediately drops the entire distance when it falls. [...] If you’d like high-altitude falls to be properly time-consuming, use the following optional rule. When you fall from a great height, you instantly descend up to 500 feet.

This guy seems to think the rules are pretty clear.

Answer 3

From page 214 of the DMG under the description for the boots:

While you wear these boots you have Flying Speed. Flying speed does not make you fly it allows you to fly when you want to, you have to willingly decide to fly.

From the Player's Handbook page 196 (emphasis mine):

If you have more than one speed, such as your walking speed and a flying speed, you can switch back and forth between your speed during your move.

Also it states:

...you can use the boots to fly up to 4 hours...

So if you use the boots by willingly deciding to move while flying, during your move then you are flying.

But the falling Optional rule from Xanathar's Guide to Everything (pg78) book needs to be taken into account here.

... you immediately fall 500ft...

Immediately means you are not allowed to do any action other than a reaction since the fall is interrupting your current turn and the only activity you can do out of your turn is a reaction, not a movement, not an action, not even a free action. Using the boots is definitely not a reaction, else it would be stated RAW in the magic item that it can be used as a reaction as an exception (like the way featherfall is written).

So, if during your turn you decide to walk (to avoid tapping into the 4 hour total duration) and move unto a trapdoor that opens under your feet; you immediately fall 500ft, then once you are 500ft lower, you can finish your move, and switch from walking to flying if you have not hit the ground yet. Otherwise you take falling damage, are prone, and can finish your movement and any action or bonus action remaining.

The same effect would happen if during someone else's turn your are pushed off a cliff. Since it is not your turn, you cannot move, therefore cannot switch from walking to flying, you fall 500ft immediately.

But if you were already flying (thus activated the 1 minute minimum flying time) then you are ok, because you are actually in flying mode and are not even touching the ground.

This is per RAW rules, not RAI. Some DM might want to allow some 'reaction' to start flying with the boots and I guess within RAI games that could be ok, but in RAW games I don't see how that is possible.