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Before I get into the details I just want to mention that I'm working in a remote area right now and don't have access to the 5e Starter Set, just the downloadable PDFs.

I'm looking for advice on how to upgrade adventures/encounters from older versions of D&D to 5e. This looks like it would be fairly straightforward for 3e and Pathfinder, although I'm not really familiar with them. For these cases the CRs of the creatures look to be fairly similar so I think you could almost use them as is. Upgrading from 4e seems like it would be much trickier since the combat mechanics of 5e are so different.

For example, look at the case of encounters A2 and A3 from Keep on the Shadowfell. A2 has a total of 13 kobold warriors, 10 minions, 1 slinger, 1 skirmisher, and 1 dragon shield. This looks like it would be way too much for a 1st level party of 5 to handle. To upgrade this to 5ed I was thinking I could just cut back the number of kobolds to something more reasonable, say 8, maybe give one or two of the kobolds some different weapons for a bit of colour, and I would have an encounter that would rate as medium difficulty.

Encounter A3 is a bit trickier because in addition to 15 various kobolds it also includes a priest and Irontooth. This is the part that I'm really struggling with, how to deal with the boss type characters so that they are still interesting and challenging but not too powerful to handle. As written just Irontooth and the wyrm priest would probably wipe out a 1st level party in a couple of rounds. I wouldn't want to just drop them from the encounter because they add something interesting and provide some hooks for moving the story along.

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Firstly, if you can you should wait for the conversion guides which will be free. If however you are anxious I suggest the following pointers.

  1. Replace all monsters from the old module with monsters from the DM basic rules. Same with common magic items. Use the xp budget guidelines to reduce or increase the number of monsters, though normally you can keep the numbers from the published adventures.

  2. Convert all skill percentages to a DC. Between 0-20% should be DC 25, from 21-40% should be DC 20, from 41% - 60% should be DC 15 from 61%-80% should be DC 10. For anything easier don't both rolling dice.

  3. For 3rd and 4th edition decide if the task is supposed to be easy medium, hard or very hard and choose the DC appropriately.

  4. For unique monsters and native items, find a monster or magic item that most closely resembles it and use Those mechanics instead.

The rest you can play as is.

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  • \$\begingroup\$ Have you ever tested or can you reference someone who has tested this system? Obviously, as you've said, there are no rules for this yet \$\endgroup\$ – Premier Bromanov Jul 20 '16 at 15:04
  • \$\begingroup\$ This is what I did for our own game. It worked fine for me and mine. \$\endgroup\$ – GMNoob Jul 28 '16 at 6:48
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All editions of Dungeons & Dragons differ in how much damage characters and monsters do, and how many hit points they have. In 5th edition characters and monsters have the highest damage output of any edition, for example this is the only edition in which a level 1 wizard with a magic missile does 3d4+3 damage, in all previous editions it was less. But the number of hit points in 5th edition is just average, and considerably less than in 4th edition.

As a consequence you cannot convert adventures from previous editions and keep the same number of monsters. As you said, 13 kobolds is way too much for a 5th edition level 1 party. The equivalent encounter in the Starter Set has 4 goblins, so for kobolds you could probably take 6 of them.

Converting adventures from 4th edition to 5th edition is particularly difficult because 4th edition D&D has a resource management system which is encounter-based, while in 5th edition resources are managed by adventuring day. Which means that in 5th edition you are more likely to have several small fights, while in 4th edition you mostly have big fights with several different types of monsters at the same time. The best conversion approach would probably be to remove ALL monsters from the original adventure and then design by yourself the number of monster encounters and number of monsters in each encounter to create a good flow for a 5th edition adventure.

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  • \$\begingroup\$ Isn't the more damage only true at lower levels? D&D 3.5e, for instance, has very high damage comboes even for mundanes, easily scoring over 200 damage on a single hit on a charge. While it's true, no published adventure that I know is calibrated to that optimization level, your sentence as is isn't true. \$\endgroup\$ – Zachiel Aug 22 '14 at 22:43
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Any time you are bringing an adventure into a system it was not designed for there are questions that can help the transition. These are generally good questions to ask when reading an adventure so you can improvise during game without breaking the adventure.

  • What are the individual set pieces of the adventure?
  • What does each encounter try and achieve?
  • What is the threat represented by the set-piece/encounter?
  • How does the encounter further the plot?
  • What does the encounter achieve?

Once you have answered these questions you also have all the information you need to follow GMNoob's advice. Tailor the mechanics (monsters and DC's) of the encounters to the threat level. As far as rewards go separate common rewards (gold, gems, items) from plot driving rewards (magic weapons or plot resources). Common rewards can be easily replaced with the most system appropriate versions. The plot driving rewards are things like magic weapons tailored to that give advantage in future encounters. These can cause problems after the adventure if is not consumed or saved by players. Finding an item or resource in the new system that you replace it in or make a foe weak to is a better option than trying to translate the original resource.

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There is always the option of replacing minions with standard monsters of the same CR or same kind (in the case of kobolds) but reducing their HP significantly. It can always be explained away as those creatures having suffered damage from exhaustion (working in the mines, or rebuilding the keep as the case may be) or possibly they are injured/diseased. Whatever the case, remember that as the DM you set the game, not necessarily the rules. Not every monster met MUST have its full hit points, any more than the monsters always meet the party with full hit points.

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