DnD Advantage and Disadvantage Explained
Advantage is one of those D&D rules everyone understands until the moment three different effects apply to the same roll. Then the game stops for ten minutes while somebody starts counting sources like they are electoral votes, and the whole point of D&D is ruined – nobody is having fun.
The basic part really is simple. If you have Advantage on a roll, you roll two d20s and use the higher one. If you have Disadvantage, you roll two and use the lower one.
This applies to attack rolls, ability checks, and saving throws. It does not normally apply to damage. You do not hit with Advantage and then roll your damage twice, no matter how much you would like that to be the rule.
Stacking conditions is usually the part that gets murky, though, so let’s try to see how we can work through it.
Let us say you are invisible, the enemy is Restrained, and another player uses the Help action. That is several different reasons for you to have Advantage, but you still roll two dice. You do not roll one extra d20 for every favorable condition. Disadvantage works the same way. One source or five sources, you still roll two dice and keep the lower result.
Then you get to the part that has caused more pointless table arguments than it probably deserves. If you have both Advantage and Disadvantage, they cancel out and you roll normally.

The number of sources does not matter.
Three sources of Advantage and one source of Disadvantage result in a normal roll. One source of Advantage and four sources of Disadvantage also result in a normal roll. You do not subtract one from the other and keep whatever is left.
I understand why people assume it should work that way. It feels logical that several advantages should outweigh one disadvantage. The actual rule ignores all of that because the alternative would have players counting every minor circumstance before each attack.
There are still reasons to have several sources of Advantage. If one effect ends, another one may still apply. They just do not give you additional dice while they are active at the same time.
You also need to read what the ability actually says. Advantage on attack rolls does not mean Advantage on every d20 you touch. Advantage on Dexterity checks does not help with Dexterity saving throws. An ability that helps melee attacks does nothing for your bow. You get the point.
This sounds obvious written down, but I have seen plenty of players shorten the entire rule to “I have Advantage” and then try to carry it over to whatever roll happens next.
The DM can also grant Advantage or impose Disadvantage when the situation calls for it. A smart plan, a proper distraction, strong evidence during a conversation, or a genuinely good ambush might earn Advantage. Describing your sword swing with more enthusiasm probably does not.
The DM also has some freedom to ignore the exact RAW interpretation when it produces a stupid result. You can rule based on what seems intended or what works better at your table. Just make it clear that you are changing the rule rather than pretending the book says something it does not.
So, the actual rule is this: roll two d20s and keep the higher one for Advantage or the lower one for Disadvantage. Multiple sources do not stack. If both apply, roll normally.
That is it. You can now return to arguing about whether the rogue was actually hidden.