How do you get more hired thugs sent after you?

[An Ning]

Just curious. I kinda enjoy killing them, but I never see them after the first time they are sent after me.

[voehringer_nitron]

I think it only happens once for a theft contract, but the murder contract might be repeatable.

[Eternie]

It happens more if you steal from good folks, so people who may be upstanding characters in the game. They don't need to see you just that you've robbed people in their town should increase the times that the thugs are sent after you.

In Solstheim the shady character Mogrul wants a 1000 gold after you get a replacement steward for Neloth the Telvanni wizard. They will keep spawning new thugs regularly ... as long as you don't pay or don't kill him.

Over in Solstheim you'll also get Morag Tong spawn and attack you, not sure what the trigger is for that though.

[вαтαк]

if you attack any good npcs a dark brotherhood assassin will come after you just like the thieves guild

Plus the thalmor will come after you if you start messing with them wich i like to do.

[Vomit Heart]

Small crimes, walk in to towns and steal cabbages ,steal coin purses from taverns etc

[Ghetsis]

Hired thugs never return to teach you a lesson. Others such as the dark brotherhood are repeatable until you complete the proper quests.

If you want to be taught a lesson though, this mod reenables hired thugs
https://www.nexusmods.com/skyrim/mods/61768