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The description for watery sphere says:

If [the sphere] moves over a pit, a cliff, or other drop-off, it safely descends until it is hovering 10 feet above the ground. Any creature restrained by the sphere moves with it.

Say I cast this spell on myself or an ally, and they willingly fail their saving throw as stated here:

Any creature in the sphere's space must make a Strength saving throw [...] a Large or smaller creature can choose to fail it.

Then, if I moved them over a cliff, would the sphere gently carry them down until it's 10 feet off the ground? Could I then cancel the spell, causing them to fall just 10 feet instead of however tall the cliff was, and negate the vast majority of falling damage?

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Yes, this would work

As you have described, since you can choose to fail the saving throw, and nothing indicates that being trapped inside the Watery Sphere makes you fail concentration or otherwise control the Sphere, you can use it to descend the cliff as you intend.

Of course, this takes a 4th levels spell slot, whereas if you had feather fall, you would only need a 1st level spell slot to achieve much the same thing. Of course, this is assuming it is on your spell list (for example, this is not the case for a Druid). So if you don't have that spell (or you don't have it prepared) then this is a possible alternative solution.

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    \$\begingroup\$ Feather fall is, in fact, strictly superior for this purpose, because there is no risk of you losing concentration and your elevator falling apart. Nor do the subjects falling suffer from the restrained condition. And you can easily use it while they are already falling. \$\endgroup\$
    – Theik
    Aug 2, 2018 at 9:06
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    \$\begingroup\$ Also Druids do not have access to feather fall but they do have access to Watery Sphere, so its kind of necessary if your the only spell caster. \$\endgroup\$
    – Youjay
    Aug 2, 2018 at 9:11
  • \$\begingroup\$ @Youjay Very true! I've updated my answer with some of these details. Feather fall isn't available to everyone, and Watery Sphere can hold 4 medium creatures, etc. \$\endgroup\$
    – NathanS
    Aug 2, 2018 at 9:16
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    \$\begingroup\$ Also, the watery sphere can hover no more than 10ft from the ground. If you make it hover only 5 ft off the ground, you will take no falling damage. \$\endgroup\$
    – Shem
    Aug 2, 2018 at 14:45

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