Story points:

1. (Optional) A New Lief

After spending a majority of his formative years living amongst wolves, Lief found himself amongst a gang of highwaymen who took advantage of his naivety to enlist him in their crimes given his skill with a bow-and-arrow. They would have him hide in the woods to fire near targets they were trying to intimidate into paying an exorbitant fee for ‘safe passage’. They lied to him by telling him they were Kings/Queensmen and it was their duty to collect a toll from all passers-by by any means necessary.

At some point, Lief left the group, although whether or not he was aware of their crimes at the time is up for debate. It seems that now he is aware that what he was doing was inherently wrong, but he believes that the bandits he worked with were good people (they aren’t) and would prefer not to encounter them again (he probably will).

2. “Leave.” (Background with a possible plot.)

Lief is a happy-go-lucky halfling who is wandering around and looking to go find his way back home. He says he was lost in the woods at a very young age one day while playing away from the nomadic halfling’s caravan. Despite that happening years and years ago, he never has really managed to get any closer to that goal and at times it seems like he’s actively avoiding it.

The only thing he remembers about the event is hearing them call his name (or something similar) as the caravan moved on with him being unable to keep up. A small part of him knows that he was abandoned (even if he’s unable to admit it to himself and chooses to keep up the false belief that he was lost and they looked for him), leading to a bit of internal conflict. He stresses the importance of finding his family and belonging, but is afraid of discovering the reasons behind his abandonment and what he may do if/when he does. He is going to try to avoid that confrontation until it seems likely that it is unavoidable.

A part of him wants answers, revenge, or maybe just resolution and, once this encounter seems inevitable through happenstance, he is going to do everything in his power to accomplish that goal; whether it’s being enlisted as a caravan guard against attack, tracking down stolen cargo/people, or a ‘great train robbery’ scenario (depending on the party’s moral compass (We have murdered a Momma Bear and killed a Basement Baby at this point.) or the caravan’s alignment). That’s up for the DM to decide.

Sorry, I really don’t know if this is a thing where we’re supposed to give plot points to follow involving character actions/goals or leave it up for the DM so I’m trying to be middle ground and leave a few options, but I’m perfectly fine with however you want to set up this adventure.

Horn of Silent Alarm (Wondrous, Common):

“This horn has 4 charges. When you use an action to blow it, one creature of your choice can hear the horn's blare, provided the creature is within 600 feet of the horn and not deafened. No other creature hears sound coming from the horn. The horn regains ld4 expended charges daily at dawn.”

Given my character’s stealth skill (and likelihood of being sent around in dumbwaiters/scouting) I’d like to have something he can use to alert the party. As it lists creatures, I’m assuming Lief would have to attune it to Awoo (wolf companion) who could (possibly) try to convey information while Lief is ahead scouting. It could be something like one blast: Come at once or two: I’m coming back with info.