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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?

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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.

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    \$\begingroup\$ i had mentioned the rate of descent in the wuote... but i also did the math and determined it was too slow for injury... but not everything is always based on science and math in these games XD \$\endgroup\$ – MC_Hambone Dec 21 '16 at 14:25
  • \$\begingroup\$ It indeed appears to be the intention that you take no falling damage. However; this is only true if you fall from the boots no longer letting you fly (duration expired, effect dispelled or other effects); it you simply get pushed off a cliff, you will take damage, unless you need 2 rounds to reach the ground (allowing you to start flying on your turn) \$\endgroup\$ – ThisIsMe Jul 26 at 7:21
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The rules do not explicitly cover this, but 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 an unofficial 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.

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    \$\begingroup\$ I'm not sure adding in the Perkins tweets helps your cause, especially with xanathars optional rule directly contradicting it. \$\endgroup\$ – NautArch Aug 27 at 1:17
  • \$\begingroup\$ Well, if Perkins is saying drop 580' in a round, but Xanathar's says 500 or less, then in one round under perkins you'd still be falling while you'd have hit the ground if following the optional printed rule in xanathar's. \$\endgroup\$ – NautArch Aug 27 at 15:57
  • \$\begingroup\$ Maybe I'm misinterpereting :) But let's say Character A is 550' above the ground. In Perkins/science land, they would still be in the air after 1 round. In Xanathar's, they'd be on the ground and getting damage. \$\endgroup\$ – NautArch Aug 27 at 16:46
  • \$\begingroup\$ @NautArch In Perkins or Xanathar's, if you were 579 feet or less above the ground, you would hit before the next round, or if you were 580 or over, you wouldn't hit until the next round. The only difference is if you were 501-579. Where it might be different is if you had not had your turn in initiative order, since instant and within one round would matter. \$\endgroup\$ – Wyrmwood Aug 27 at 18:45
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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.

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    \$\begingroup\$ Friendly Suggestion: I'll recommend reviewing how to write a good answer if you want your answers to get favorable responses. I predict that this one will attract down votes. \$\endgroup\$ – KorvinStarmast Jul 23 at 17:52
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    \$\begingroup\$ Edited. I was just assuming the RAW rules were easily known I stated all references now and enhanced the post. \$\endgroup\$ – KilrathiSly Jul 26 at 1:17
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    \$\begingroup\$ @KilrathiSly Thanks! We try to encourage all answers to explicitly cite their sources even if they are well-known and accepted. After all, these answers are here to help those who don't or may not be familiar at all with the rules. I've removed the notice from your answer. Thanks again! \$\endgroup\$ – Rubiksmoose Jul 26 at 3:17
  • \$\begingroup\$ I like the way you upgraded the answer, but I suggest that you clarify that the "rule" you cite from XGtE is an optional rule. Because it is. Something like "if your are applying the optional rule from XGtE, then you fall immediately ..." and so on. \$\endgroup\$ – KorvinStarmast Jul 26 at 12:50
  • \$\begingroup\$ This is clearly one of the aspects of the game where 'GM rulings VS rules' is the way to go. This is not the only item/spell/class feature which imply many questions the rules don't and won't ever answer about 'flying vs falling', since D&D's rules are written with the intent to be as clear as possible without tying everything up in a nice logical bundle that tackles every possible discrepancies they create. And when I mention "GM rulings" I'm just influenced by everyone using this term, I think the appropriate one is "Groups rulings" since many GMs are open to suggestions \$\endgroup\$ – Catar4 Jul 28 at 23:44

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