Live and Learn

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Fast. Play after a skill test you failed ends (after resolving all effects from the failed test) .

Attempt that test again. You get +2 skill value for this test.

Old Hunting Rifle

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Spend 1 ammo: Fight . You get +3 fight and deal +2 damage for this attack. If a skull or tentacle symbol is revealed during this attack, the rifle jams. (This attack automatically fails. Before you can activate this ability again, you must perform the following ability: [action]" : You clear the jam.")

What happens if you draw a skull or tentacle token with the Old Hunting Rifle and then play Live and Learn?

You can repeat the test as usual just like any other failed test - you will make another +3 fight/+2 damage attack against the same target, and you don't have to spend any additional actions or ammo to do so. You won't get the benefit of any skill cards or one-time boosts (e.g. from Scrapper) from the first test.

Regardless of how the second test goes, the gun is still jammed.

The thing to realise with Live and Learn is that you repeat the test itself , without needing to pay costs. When the Old Hunting Rifle is jammed, you can't activate the fight ability any more - Live and Learn doesn't reactivate the ability or anything, it just repeats the test. It's a subtle distinction, but it can be important in cases like this, or in situations where the original action was on an Event card or was a one-time deal (you can even use Live and Learn to repeat tests on Treachery cards, though doing so is generally a bad idea outside of niche situations).

In that case, for the sake of my head cannon I am going to pretend Live and Learn causes the investigator who jams their gun to flip it over and try smacking the monster with it.