D&D 5E Should you always fail on a 1 and always succeed on a 20 for every d20 roll?

[Satyrn]

Now you add to that a DM who insists on a die roll for every skill performed and you compound the above issue.

Aye, this is why I have been advising the OP not to ask for skill checks for trivial, routine checks.

And also, for critical or dangerous situations (like the example of sneaking past a hundred guards) I have been advising that he reduce the whole thing to as few checks as possible.

The OP is looking for a way to incorporate getting unlucky to his checks. The big thing I want him to consider when implement autofail on a 1 is this:

1) When you only have to make one check, rolling a 1 will indeed feel unlucky.
2) When you have to make several checks - even just 3 or 4 - you will feel lucky if you don't roll a 1 because the odds of doing so skyrocket.

Number 2 is what needs to be avoided.

 

[Mistwell]

You should not always fail on a 1 for everything. Because that means ANYTHING carries a risk of failure and thus requires a die roll, which slows the game down. If your bonus is such that rolling a 1 would still result in success that should be the line where the DM doesn't need you to roll because it's a thing you have mastered.

 

[Satyrn]

If it is impossible to fail, why are you even rolling?
Likewise:
If it is impossible to succeed, why are you even rolling?

Therefore: If you are rolling a d20, there must both be a range for failure and a range for success. Because otherwise there is no point in rolling.

This means, by the default rules of the system, a 1 should always be a failure and a 20 should always be a success, as those are the static endpoints for their respective ranges of numbers.

The exception to this would be if you were using an alternate numbering system, such as one where lower numbers meant passing and higher numbers meant failure.

I disagree with your point because you've apparently answered the bolded question differently than me. Or, the question isn't exactly set up to reflect the process I use.

As a DM, I don't rule that failure or success is impossible to fail. Rather, I simply rule on if the failure or success occurs, or I ask for a roll.

Now, at this point it may be that success or failure is impossible because I've set a DC that makes it so, and I ask the player to make a check without knowing his modifier.

So to answer your question - If it is impossible to succeed, why are you even rolling? Because the DM told me to.

 

[EvanNave55]

See this whole thing is why I would prefer to play the game with a house rule I made. I do think there should be a chance your really unlucky and make a mistake or miraculously lucky and get that success for things however a 1/20 or 5% chance seems way to common to be incredibly/miraculously (un)lucky. That's why I would prefer something like roll 2d10 and double 1s/20s are the auto fails or successes.
In addition this makes it so the average results (things like 7-13 on a roll) are more frequent than the extremes which I also would really prefer.

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