Manbearcat
Legend
I can't understand any of that, but the answer seems pretty simple to me: silent means silent. Automatic success on all attempts to move silently (basically you never have to roll stealth again).
Ok. We have so far in the playtest:
- Hide/Move Silently married as "Stealth".
- Spot/Listen married as "Perception".
- Stealth Mechanical Resolution Rules. These rules specificially speak to the "Hide" and "Spot" portion of the Stealth

- Now we have a Cloak of Elvenkind that interacts with the "Hide:Spot" portion of the Stealth Mechanical Resolution Rules (bypasses prerequisite for conceleament). This would seem to set the standard for what the corresponding Boots "should" do. Right?
- Wrong. The Boots have no such "Move Silently:Listen" mechanical resolution portion of the Stealth rules for them to interact with. There is no (i). We have (ii) . But (ii) is nowhere to be found in the Stealth Rules. It is in the Equipment rules and its only detached reason by proxy of implication.
So then. We either have:
- Boots that do nothing because there are no corresponding Stealth rules that will give the wearer advantage.
- Boots that cancel disadvantage on Stealth checks over antagonistic terrain (dry leaves, gravel, etc) such as the disadvantage alloted to heavy armor wearers.
- Boots that cancel advantage on percievers' Listen checks to hear the person moving over antagonistic terrain.
Oddly incoherent and left up to interpretation. The rules are silent on this Move Silently:Listen relationship but they speak explicitly and directly the to Hide:Spot analog (indicating relevance and precedent). Therefore, many a group may never impose disadvantage on Stealth or give advantage on Listen in these scenarios. It thus opens up the paradigm whereby this vacuum of rule-space all of a sudden changes once a PC gets these Boots (in order to make the boots useful). All of a sudden, people are ad-hoc retrofitting a Move Silently:Listen rule and hard-coding it into their game so the wearer of the Boots has some mechanical advantage/use from the magic of the boots.
Thus:
Why is the rule not there in Stealth Rules in the first place? And then why is there no corresponding rules crunch (such as cancelling user disadvantage on Move Silently or cancelling contestant advantage on Listen) on the Boots?
It seems to me this is either (i) Right Hand/Left Hand design incoherency, (ii) design oversight, or (iii) a "Rulings not Rules" feature....which, of course, will just become an ad-hoc, retrofitted Rule for every single table once these Boots find their way into the game (or magical Boots of Elvenkind will have no mechanical functionality).
That is my 3rd attempt. I hope that makes sense.