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Magic Circle has the following effect on creatures of a specified type:

The creature can't willingly enter the cylinder by nonmagical means. If the creature tries to use teleportation or interplanar travel to do so, it must first succeed on a Charisma saving throw.

Otiluke's Resilient Sphere states:

Nothing - not physical objects, energy, or other spell effects - can pass through the barrier, in or out, though a creature in the sphere can breathe there.

Does the quoted effect from the Sphere beat the quoted effect from the Circle? In other words, could a creature of a type affected by a cast Magic Circle enclose itself in an Otiluke's Resilient Sphere and freely roll themselves into the cylinder of the Magic Circle?

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    \$\begingroup\$ they see me rollin', they hatin' ... \$\endgroup\$
    – PixelMaster
    Apr 5 '19 at 9:55
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    \$\begingroup\$ @PixelMaster and, of course, the Weird Al version "Got skills, I'm a champion at D and D". The circle is complete. \$\endgroup\$
    – Reginald Blue
    Apr 5 '19 at 14:12
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Yes, you can enter the circle

The resilient sphere effectively excludes anything it encloses from outside spell effect areas. As the effect of the magic circle originates outside, it does not have any effect on a creature rolling inside the sphere, as it is not considered to be in its area of effect.

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Based on an entirely legalistic reading of the spell descriptions, it seems as if they do not interact in any meaningful way.

Specifically:

The creature can't willingly enter the cylinder by nonmagical means.

Rolling oneself across the barrier of said circle within a magically conjured resilient sphere is, arguably, a magical means of entry and so unaffected by the prohibition. It's also not a form of teleportation or interplanar travel, so it wouldn't even require a Charisma check.

Extension of this particular semantic argument to a broader scope would suggest that one can also freely enter the cylinder provided one levitates in, spider-climbs in, or walks across while wearing magic shoes. Obviously, this is deeply silly.

Unfortunately, to the best of my knowledge no more authoritative answer is available. It is very difficult to effectively prove a negative, but I have not been able to find any (e.g, designer's) statement on the interaction of these two spells. That may change; until it does, all you can do is choose to rule it (presumably differently from said ridiculous legalistic interpretation) according to your taste.

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    \$\begingroup\$ Aren't cylinders closed at the top and bottom? Levitating in shouldn't work \$\endgroup\$
    – Pierre Cathé
    Apr 5 '19 at 11:26
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    \$\begingroup\$ @PierreCathé Because it's a magical means, not because they'd go over the circle. \$\endgroup\$
    – Miniman
    Apr 5 '19 at 11:37
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    \$\begingroup\$ Ah my bad, that seems legally correct, although it feels wrong \$\endgroup\$
    – Pierre Cathé
    Apr 5 '19 at 11:40
  • \$\begingroup\$ Thanks for the answer. Is there anything to suggest whether or not, if hypothetically this legalistic interpretation did not mean you could use any non-teleportation magic to enter the cylinder, that the Sphere blocking spell effects would be a separate reason it (and not, e.g. Levitate) could get you into the Circle? \$\endgroup\$
    – Vigil
    Apr 5 '19 at 12:58
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    \$\begingroup\$ How is walking wearing magic shoes not a nonmagical mean? The shoes don't enable the walking (unlike how levitating, rolling on a sphere, and spider-climbing necessitate the magic for the action). \$\endgroup\$
    – David Coffron
    Apr 5 '19 at 13:11

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