Willem Renzema's answer to "Can you Investigate the same room twice?" and abalonemacaroni's answer to "I failed to open a lock. Now what?" seem to lean towards the idea that if an ability check can be repeated indefinitely given enough time, a drawback should occur on each failed attempt to offset that.

But how can I resolve a repeatable skill check when there's no time constraint or clear drawback from repeating it?

For example, making a History check in a library, lockpicking a safe that you've already stolen and brought back to your hostel, or making an Investigation check on an emptied dungeon, etc.

Basically, it feels like they are going to succeed in both cases, and the roll looks useless.

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    \$\begingroup\$ This answer talks about what to do if there is no drawback to attempting something; namely, don't get them to roll: rpg.stackexchange.com/a/49242/45088 \$\endgroup\$ – L0neGamer Jun 20 '20 at 20:33
  • \$\begingroup\$ why call for a roll in this case? you have not explained why you are asking for a roll. what are the stakes of success or failure? Explain that and you will get better answers. \$\endgroup\$ – KorvinStarmast Jun 20 '20 at 22:40
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    \$\begingroup\$ Instead of thinking of a skill check as "can I do this thing this one time" think of the skill check as "can I do this thing at all". If you fail, maybe it means you simply can't figure it, and additional time won't help, so there are no further rolls for that character for that task. \$\endgroup\$ – tobek Jun 20 '20 at 22:47
  • \$\begingroup\$ @tobek a roll could even mean that it takes you some time to complete the task \$\endgroup\$ – L0neGamer Jun 21 '20 at 0:10

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