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Grease in 5e states that a character who fails a DEX save goes prone. It takes half their movement to get up. If a character can move 30 feet/round - then the character can exit the greased area because the greased area is just a 10 feet square.

Does that effectively mean that the most amount of time any character or creature will typically be caught is one round?

OR...does that character have to roll again if they enter another 5 foot square of grease?

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It at most forces one save per turn.

If the creature remains in the greased area, then it might have to save again if it is not already prone. But if it starts its turn in the grease (prone or not) and then exits, it is still difficult terrain. So you want to make sure the enemies will be forced to cross the grease, or at least can't just exit by moving closer to you.

When the grease appears, each creature standing in its area must succeed on a Dexterity saving throw or fall prone. A creature that enters the area or ends its turn there must also succeed on a Dexterity saving throw or fall prone.

So the only moments a creature must make a save are:

  1. When the grease appears
  2. When the creature enters the area
  3. When the creature ends its turn in the area

However, you are interpreting the spell wrong.

It is not a spell meant to keep people prone. It is a battlefield control spell. Need to cover the party retreat? Grease the tunnel behind the last person. Want to make the enemies take longer to get to melee range? Grease between you and them.

Enemies will lose 20ft of movement to cross the greased area in the best scenario (for the enemies).

Also notice it does not use up concentration, and this is a big plus.

There is this video by nerdarchy about using the spell. Except they got it wrong in the first segment. Grease is not flammable. And they got the burning hands spell damage wrong.

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    \$\begingroup\$ Best scenario. Worst case - they enter the grease, fall prone, waste movement standing and then end their movement in the next square, fall again and lose more movement the next turn. \$\endgroup\$ – James Alday Dec 9 '17 at 16:24
  • \$\begingroup\$ @JamesAlday Unfortunately it is only forced to save again if it ends its turn in the greased area. Since it is already inside the area, it can exit using its movement. \$\endgroup\$ – Mindwin Dec 9 '17 at 19:34
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    \$\begingroup\$ 30' movement - move into grease (-5 ft.), fall prone & stand up (- 15 ft.), move through difficult terrain (-10 ft.). They either end their turn in the grease or dash to get out of it, losing their action as well as some movement. Combine with a warlock that has Repelling Blast and watch the slapstick ensue. \$\endgroup\$ – James Alday Dec 11 '17 at 15:43
  • \$\begingroup\$ @JamesAlday Except given that the Grease is only 10 feet square, and the person is already one 5’ square in, wouldn’t that last 10 feet of movement take them right out of the Grease? \$\endgroup\$ – Praxiteles Jan 25 '18 at 4:40
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    \$\begingroup\$ Of course you can spend more than one turn in the grease. "Move into grease (-5 ft.)" - this assumes the creature was standing right near the grease, which is not always the case. \$\endgroup\$ – enkryptor Jan 25 '18 at 9:36

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