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One of my players is playing a Way of Shadow monk, and really likes the Shadow Step ability. However I have been having two issues with DMing effectively for him:

  1. Describing the shadows. I haven't really figured out a way of displaying shadows well on a digital map. I'm not exactly an artist and, since we use Roll20, I mostly used pre-rendered maps. So what ends up happening is he will ask, “Where are the shadows?” and I have to, rather un-immersively, say there a shadow 20 feet away, etc. I suspect it ends up feeling like the shadows wouldn't be there if he hadn't asked.
  2. Making the shadows useful. I'm not positive if this is a problem or not, but so far the shadow step ability — while interesting — has not actually aided him in any way. This may be related to the first issue.

So basically: How can I make Shadow Step more readily useful in Roll20?

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    \$\begingroup\$ This was asking for a list of ideas and already drawing close votes, so I was about to close it as “opinion based”. But I noticed that the bold question at the end was not actually a match for the problem described, so instead I changed it to actually ask how to solve the problem described. That should keep it open, and also make it more possible to answer in our Q&A format. How does it look to you? \$\endgroup\$ – SevenSidedDie Sep 11 '16 at 16:47
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Get Plus or Pro

If you use Plus or Pro, Dynamic Lighting is available. That wiki page has a lot of info for helping you set-up and use the lighting.

Note from the top of that page:

This page is about a feature exclusive to Plus and Pro subscribers, or to players in a game created by that subscriber. If you'd like to use this feature, consider upgrading your account.

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    \$\begingroup\$ Just want to say that I absolutely love the Dynamic Lighting Feature and it has helped immensely with line of sight and other issues, and also sets a much better tone when dungeon crawling. I can create shadows all based on where light sources are. Much Shadowstepping going on. \$\endgroup\$ – Airatome Sep 12 '16 at 3:28
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    \$\begingroup\$ To add to this specific request, be warned, Dynamic Lighting doesn't do well representing daylight. The best thing for daylight is several infinite-radius light-sources set to apply low-light to everywhere, then to apply several light-sources for bright-light in the direction you plan the sun to come from. \$\endgroup\$ – Cyberspark Sep 12 '16 at 9:33
  • \$\begingroup\$ This begs the question on how to do it without Pro, or with premade maps that aren't in a program with dynamic lighting. \$\endgroup\$ – Jason_c_o Dec 15 '18 at 9:12
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The main way to make Shadow Step more useful would be creating conditions where normal movement to a certain location is difficult but it's desirable for somebody to get there.

For example, say there are archers shooting at the party from a balcony. In addition to being raised, the wall gives them cover, so getting in there behind them would be better than just returning fire with ranged attacks.

Or, one of the foes is running away with something valuable while the others block the path behind them. Shadow Step would allow cutting off the escape.

Or, outside of combat, there's a hazard (a big pit of fire, for example) that can only be shut off from the other side. Or a spot that can be seen into, but not (normally) accessed without noisily breaking down a section of wall.

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