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The entry for Mason's Tools within XGE (p83) lists this as one of the proficiency's benefits:

Demolition. Your knowledge of masonry allows you to spot weak points in brick walls. You deal double damage to such structures with your weapon attacks.

It then lists this as one of the possible activities:

Find a weak point in a stone wall [DC 15]

One might interpret this to mean that you must make a successful DC15 check with the Mason's Tools before being able to deal double damage to a stone structure with your weapon attacks.

Another might read these as isolated entries, believing that your proficiency with Mason's Tools automatically allows you deal double damage to stone structures with your weapon attacks as a passive benefit. Meanwhile, successfully performing the tool check above bestows its own separate benefit.

Obviously, the confusion lies in their using the phrase "weak point" in both the Activity as well as the Demolition feature. However, if read literally, the Demolition feature does explicitly state "You deal double damage to such structures..." and not "you deal double damage to weak points within such structures...".

So, to word this as questions:

Do you need to perform to a successful tool check to benefit from the Demolition feature of the Mason's Tools?

And if not, what would be the benefit of finding a weak point in a stone wall with a successful check of the Mason's Tools? (For example: Would a weak point within a stone structure simply have fewer hit points than the rest of that structure?)

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  • \$\begingroup\$ Can you clarify where you are finding this information? Page 154 of my PHB does technically indicate that Mason's Tools exist, but there is no information on "proficiency benefits" for those or any other tools and in fact Mason's Tools don't even have their own description and are instead a type of Artisan's Tools which "lets you add your proficiency bonus to any ability checks you make using the tools in your craft" and has no further details about what benefits proficiency may bring. I suspect you have unintentionally stumbled upon homebrew. \$\endgroup\$ – Kamil Drakari Dec 12 '20 at 7:01
  • \$\begingroup\$ @KamilDrakari it's not homebrew, but it isn't from the PHB; the OP is quoting the tool proficiency optional rules section of Xanathar's Guide to Everything. \$\endgroup\$ – Carcer Dec 12 '20 at 9:38
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    \$\begingroup\$ @KamilDrakari My apologies. Carcer is correct. I made a mistake sourcing my information. The information that I am quoting is found on page 83 of XGE. \$\endgroup\$ – Buggy Buggman Dec 12 '20 at 23:18
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Demolition does not require any check

The wording is indeed ambiguous on its own, but a comparison with other Tool Proficiency benefits leads me to believe it would be explicit if a check were required. Here are some examples of proficiency benefits which require checks:

Decipher Treasure Map. This tool proficiency grants you expertise in examining maps. You can make an Intelligence check to determine a map’s age, whether a map includes any hidden messages, or similar facts.

Craft Hidden Compartment. With 8 hours of work, you can add a hidden compartment to a pair of shoes. The compartment can hold an object up to 3 inches long and 1 inch wide and deep. You make an Intelligence check using your tool proficiency to determine the Intelligence (Investigation) check DC needed to find the compartment.

Quick Fake. As part of a short rest, you can produce a forged document no more than one page in length. As part of a long rest, you can produce a document that is up to four pages long. Your Intelligence check using a forgery kit determines the DC for someone else’s Intelligence (Investigation) check to spot the fake.

Since several other proficiency benefits explicitly state when a check is needed, while I can find none which explicitly state that no check is needed, I believe the correct interpretation is that any benefit which doesn't mention a check does not require one.

How do I attack weak points if I haven't found them?

A potential new confusion arises: If I can find weak points to attack without a check, why is there also an option to find weak points in general which requires a check? The best answer I can find is that Demolition doesn't actually require that you attack weak points to gain the benefit, thus you don't need to find them. Demolition doubles damage to "such structures" as brick walls, which is significantly different wording to an otherwise similar benefit from Glassblower's tools:

Identify Weakness. With 1 minute of study, you can identify the weak points in a glass object. Any damage dealt to the object by striking a weak spot is doubled.

Since the Glassblower's tools benefit specifies "striking a weak spot" deals double damage, while Mason's tools do not specify that attacks must strike a weak spot to deal double damage, I would argue that using Demolition to double damage against a structure does not need you to actually find the weak points and so it doesn't overlap with the example ability check. As for what you would accomplish by finding weak points with the check if it's not necessary for the damage, I would say it still has broader roleplay uses. For example, perhaps you could find a weak point and then fortify it rather than destroying it. Or perhaps you could then direct other players or NPCs to attack the weak point, gaining a benefit even though you are not making a weapon attack yourself. Many of the suggested checks for various tools give information that doesn't have any inherent mechanical consequence, so it is normal that the player and DM need to make their own interpretations for how that information can be used.

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  • \$\begingroup\$ This answer is incredibly helpful. I feel a fool for not realizing I might be able to glean more information from other tool proficiencies. "Decipher Treasure Map" and "Identify Weakness" do seem to be very telling of the intent of "Demolition's" wording. Thank you very much for what appears to be a very thorough effort. \$\endgroup\$ – Buggy Buggman Dec 13 '20 at 13:09
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A brick wall is not the same as a stone wall. enter image description here

Although I do not know if this difference was intented by the creators.

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    \$\begingroup\$ A funny and fair point that my original question overlooks. So, with this understanding, the player deals double damage to brick walls – no check necessary. Meanwhile, they can make a check to find a weak point in a stone wall, which provides them no added benefit whatsoever. I'll run this by the group next session, thank you! (lol) \$\endgroup\$ – Buggy Buggman Dec 11 '20 at 23:17
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    \$\begingroup\$ @BuggyBuggman I quess it up to the players to decide what to do with a found weakspot and up to the DM to decide if it works/ what the effects are. \$\endgroup\$ – Edwin Stoteler Dec 11 '20 at 23:36
  • \$\begingroup\$ Note that the image of a "stone wall" you have is clearly also a brick wall, just of a different sort of brick. Still a good point, though, since in a setting with magic non-brick stone walls may exist (whereas in real life they are exceedingly uncommon). \$\endgroup\$ – Please stop being evil Dec 13 '20 at 7:56
  • \$\begingroup\$ @Pleasestopbeingevil No the stone wall is not a brick wall. Bricks are human made with clay. Stones and bricks are two different things. \$\endgroup\$ – Edwin Stoteler Dec 15 '20 at 9:36

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