Uploaded February 2026 | Updated September 2026, 5 hours ago
A character tries to roll a skill check in D&D, Pirate Borg, or another RPG. They fail. Can they try again? We examine when to call for checks, the impact of success and failure on story and fun, using degrees of success, and other techniques for Dungeons & Dragons or your choice of RPG.
Contents:
00:00 Intro
00:26 Not Just for D&D
01:14 Grappling Hook Scenario
02:04 Why Trying Again Isn't Usually Allowed
04:03 Should it Even be a Check?
06:03 Deciding the Impact of Failure
09:05 Failur that Drives Choices and Options
10:22 Clear Stakes
14:29 Is Failure a Problem?
16:27 Should Success be Possible?
17:39 Degrees of Success or Failure
21:12 The Problem with Multiple Checks
23:24 Is it the Right Check?
25:26 Support the Show
Support me and join our community to help shape this show (and get a copy of my Adventure, Encounter, and Monster Design Tools): alphastream.org/index.php/support
You can find more RPG and D&D insights on my blog, alphastream.org
Subscribe to my newsletter to receive a FREE product and get updates on new RPG products and blog posts! alphastream.org/index.php/subscribe-to-alphastream-org
Follow me on Mastodon: https://dice.camp/@Alphastream
Follow me on Patreon: patreon.com/Alphastream
#DnD #ttrpg #tabletopgames #rpgs #dungeonsanddragons #tabletoprpg #PirateBorg #DrawSteel #Daggerheart #dungeonmaster #dmadvice #dungeonmasteradvice #dungeonmastertips
A character tries to roll a skill check in D&D, Pirate Borg, or another RPG. They fail. Can they try again? We examine when to call for checks, the impact of success and failure on story and fun, using degrees of success, and other techniques for Dungeons & Dragons or your choice of RPG.
Contents:
00:00 Intro
00:26 Not Just for D&D
01:14 Grappling Hook Scenario
02:04 Why Trying Again Isn't Usually Allowed
04:03 Should it Even be a Check?
06:03 Deciding the Impact of Failure
09:05 Failur that Drives Choices and Options
10:22 Clear Stakes
14:29 Is Failure a Problem?
16:27 Should Success be Possible?
17:39 Degrees of Success or Failure
21:12 The Problem with Multiple Checks
23:24 Is it the Right Check?
25:26 Support the Show
Support me and join our community to help shape this show (and get a copy of my Adventure, Encounter, and Monster Design Tools): alphastream.org/index.php/support
You can find more RPG and D&D insights on my blog, alphastream.org
Subscribe to my newsletter to receive a FREE product and get updates on new RPG products and blog posts! alphastream.org/index.php/subscribe-to-alphastream-org
Follow me on Mastodon: https://dice.camp/@Alphastream
Follow me on Patreon: patreon.com/Alphastream
#DnD #ttrpg #tabletopgames #rpgs #dungeonsanddragons #tabletoprpg #PirateBorg #DrawSteel #Daggerheart #dungeonmaster #dmadvice #dungeonmasteradvice #dungeonmastertips
