D&D 5E Fun with Supernatural Patrons

[meomwt]

Sounds like the Crow/ Imp should be about making the Warlock's sister get into trouble - she is an agent of a Deity, after all. Maybe the Crow "accidentally" gives away her position in an ambush, calls her nearer to the Bad Guys when the warlock is about to unload an Area of Effect bomb, or gets in her way when she is trying to cast a spell. Sow seeds of discontent between the siblings.

Sometimes, it's the little things which matter...

 

[Unwise]

In my game a PC found themselves beholden to a devil, but was a good person so would refuse to do anything extreme. So I took a leaf out of Stephen Kings Needful Things. He is called upon to leave practical jokes behind, say slightly hurtful things or tell tiny lies. The thing is, the devil knows exactly what needs to be said and done to cause feuds and end lives. He can sense the negative emotions of those around him. So he plays up peoples jealousy, resentment and self-loathing.

The PC stole a minor item, that unbeknownst to him caused a lady to kick out a recovery junky she had staying with her, as he was the logical suspect. The kid ended up back on drugs and spiralling towards a grim end. He told a guy considering suicide that he was hopeless. He stole a letter that would have reunited a man and his long lost son. All pretty terrible stuff from very minor actions.