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If one stands at one end of a teleportation circle and tries to cast a spell through it to affect something around where the destination circle is, would it work?

My concern is that a teleportation circle might not be enough to count as "a clear path to the target".

Assume you cannot see the destination teleportation circle but that the spell also doesn't require sight. Assume the spell does require a clear path.

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No

Teleportation Circle only affects creatures, not effects, per the text of the spell:

Any creature that enters the portal instantly appears within 5 feet of the destination circle or in the nearest unoccupied space if that space is occupied.

The creation of the portal between points permits the passage of creatures from point to point, but does not expressly permit effects to pass through.

Whatever hypothetical spell you utilize is not a creature (unless it were some sort of summoning spell) and thus cannot affect something on the other side. Even if it was a summoning, you do not have line of sight to your end point destination to summon the creatures at that location. You could summon them into the portal right as it opened and have them pass through, though I doubt that's what you're envisioning.

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    \$\begingroup\$ Beat me to basically the same thing... but a strict reading of the spell also means you arrive naked at the destination as objects aren't affected either. :) \$\endgroup\$ – Slagmoth Aug 22 '18 at 18:41
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    \$\begingroup\$ @Slagmoth really makes guard duty at the Waterdeep teleportation circle interesting. \$\endgroup\$ – Pyrotechnical Aug 22 '18 at 18:47
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    \$\begingroup\$ It's also worth mentioning that you come out at an arbitrary point to avoid colliding with an existing creature, so the boundary of the circle doesn't map in a continuous way to the destination area. It really isn't a clear path at all. \$\endgroup\$ – Mark Wells Aug 22 '18 at 19:35

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