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I'm playing a 5e D&D homebrew campaign and we are all new to D&D, we don't know all the rules.

So I'm wondering: can you make a multiple rolls for one task? For example: I'm trying to spot something unusual on a ring and I get a low roll, then my DM says I didn't notice anything unusual then I say I try again then I get a higher roll and my DM says I saw that I saw. That seem a little odd, also when you fail a check and another player in the party tries to do that it doesn't seem realistic.

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    \$\begingroup\$ Your question has multiple parts, and I think both parts are addressed by existing questions. I've linked the first one, and here is the second: rpg.stackexchange.com/questions/22902/… \$\endgroup\$ – Icyfire Apr 20 '17 at 20:50
  • \$\begingroup\$ The example in the duplicate question is quite different from the one in this question. The linked question's answers seem DM oriented ('how to avoid such situations', 'when should you ask for a roll') and might not help OP in his situation. Also, his example includes the possibility of a disparity between player and character knowledge. \$\endgroup\$ – Thyzer Apr 20 '17 at 21:17
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    \$\begingroup\$ Duplicate-status of this question under discussion on Meta here. \$\endgroup\$ – nitsua60 Apr 21 '17 at 2:04
  • \$\begingroup\$ I see the question is closed, but I want to clarify regardless - as a player you are not supposed to choose when and what roll do you make. It's the DM who says "make a X roll". The player can say "I do this", "I try to do that again", neither "I'm making X roll" nor "I want to roll the same skill again". \$\endgroup\$ – enkryptor Apr 21 '17 at 7:31
  • \$\begingroup\$ Not sure if this is in the 5e rules, but for "knowledge" type skills like this the GM should be making a secret roll (e.g. behind his screen) and telling you the answer. If you don't see anything unusual about the ring, you shouldn't know whether it's because you rolled low or because there is nothing unusual about it. The GM would say "You examine it for x time but can't see anything unusual". You could try again, but IMHO the GM should apply a penalty to the recheck because you may have failed because you don't know what to look for rather than just not noticing it. \$\endgroup\$ – colmde Apr 21 '17 at 8:45
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Ultimately it's your DMs choice whether he allows it or not, but...

The Dungeon Masters Guide recommends (p. 237) that

Sometimes a character fails an ability check and wants to try again. In some cases, a character is free to do so; the only real cost is the time it takes.

This tasks would be stuff like picking a lock (assuming nothing breaks), everything, where you can see that you failed, but the circumstances didn't change.

[...] In other cases, failing an ability check makes it impossible to make the same check to do the same thing again.

This would be a check where the circumstances change, like in a discussion, social interactions, when something breaks, etc.

I would personally add a third category of failed checks. The ones where you don't know that you failed.

If you try to open a door or pick a lock and it doesn't open - you know you failed and you try again.

If you look into the distance or check a ring for something unusual and you find nothing - you haven't found anything, and you would think that it is a normal ring and tell your party members so. You might give it someone else to have a look at it, and it might be realistic if you have someone with a keen eye in your party, but your DM could consider it meta-gamey.

Even if you as a player might think "this has to be a special ring" your character is sure that he found nothing. - You have to differentiate between player knowledge ('This has to be awesome loot') and character knowledge ('Well, it seemed normal').

If you saw someone do something special with this ring you might be able to Identify it.

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