Dungeons & Dragons Online

How to help new players understand rolls?

TL;DR- My players seem to expect to be able to bend reality to their whim, or force NPCs to react in certain ways if they just roll high enough or argue with them long enough in-character. Despite my never allowing this to work, they continue to try. How do I get them to understand that while they’re free to attempt anything they want, a nat 20 or compelling argument don’t guarantee things that are truly absurd?

A little more context: I’m a new DM (this is my first campaign, and I’ve never played in one either) for a group of 7 players in a Curse of Strahd campaign. 4 of the players have never played before at all, and have no exposure via CR or any similar streamed games. 1 player has played a partial campaign years ago, but never since then, another had just started playing back in November, and the final player has a few campaigns under his belt. This leads to fairly frequent OOC discussions on rules/explanations, but that’s to be expected with this many new players and we’re all still enjoying the game.

The issue I’m having as DM is the new players seem to think they can do literally anything they want, they just have to roll high or argue long enough. A few actual examples from our game last session:

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-The rogue broke into Rictavio’s cart and stole all of his vampire hunting gear with a high stealth and sleight of hand roll. Nobody else was really around, so fair enough. However, obviously someone like Van Richten isn’t the type of person to just ignore the fact that he’s been robbed blind, and he eventually tracked her down and demanded his belongings back. This led to a 5 minute in-character argument about why she should get to keep his crossbow that she stole, despite failed deception/persuasion rolls, his escalating threats towards her, and accusations that she’s in league with Strahd. She eventually returned it, very begrudgingly, and at the insistence of a fellow party member.

-The bard rolls up to the Wizard of Wines and says he’s the wine inspector here to check the wine, for no real apparent reason other than his character is something of a compulsive liar. All fine and good, I don’t mind shenanigans, but obviously the owner of the winery isn’t going to buy that regardless of how high he rolls on deception (he rolled a nat 20, for the record) due to the nature of the claim and the setting, and player was genuinely disappointed by this and continued to insist throughout the entire winery encounter that he was an inspector, and tried to initiate further rolls to convince the owners as such. No real in-game consequence, but it eventually led to other players cutting his character off because they were tired of the bit.

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I’ve tried explaining to them OOC that certain things are just plain unachievable, but these types of situations continue to arise. I don’t really mind them too much, personally, but it clearly takes up a lot of time during social interactions when one character decides to commit to an impossible task, and takes that time away from the other players getting to try things. Sometimes it can even lead to the situation going very south, inconveniencing the entire party.

So my question is, what can I do to mitigate these situations? I’ve tried spinning them into fun twists, mild consequences for their actions (nothing malicious, things like the now-angered shopkeep not giving them as good of deals on gear), and actual game mechanic explanations that some things just won’t work. I guess I’m just looking for advice on how to help the party to learn their limits while keeping it fun for those who already understand, and also how to deal with it personally as it’s beginning to wear on me a bit as DM.

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