So this is something that has been bugging me for a long time. I am RP a character and have a certain progression path planned out. I started with the Companions, continued with the Thieves guild and was hoping to the Dark Brotherhood next and then move onto the civil war quests and finally the main quest.

I recently completed the main quest chain for the thieves guild, However, I had completed "Innocence Lost:" a really long time back. This was way before I had even started the Thieves quests. I have probably completed around 2-3 weeks of in game time since then and still have had no contact from the dark brotherhood, neither have I had a courier come and give me a note.

This is my second play through and I clearly remember coming across the courier the very next day in Riften after completing "Innocence lost".

Has anyone else had similar experiences or is my game bugged for good?

Sleep in a home you own or an Inn for at least 8 hours, then fast travel to another city. This seems to be the most common 'fix' to this bug that I have seen. I've also seen some people repeat it 2 or 3 times and upon 'waking' they are moved during sleep to where the quest starts, skipping the courier entirely.

Did you sleep yet? I know the courier should come first, but I would give it a shot.

Do you have Hearthfire? Cos I do, and the Dark Brotherhood won't contact me, either, and I've also been to sleep/done the extra Cicero mission/handed in the Aventus mission etc.

Yup. I've literally done the "sleep and travel" thing multiple times now. I've slept in every inn in every city I've traveled too.

And no, I don't have Dawnguard or Heartfire.

I am only assuming that the courier keeps missing me when I travel from city to city.

Does anyone know how exactly the "courier" system works in the game? Do they like travel by foot if they miss you in one hold to the next hold you are in?

Are you sure you remembered to return to the Arentino kid to tell him that the job's been done?

Want to read an intriguing story? After some time Ive finally reached save 666, and by complete coincidence I had started a new character and the mark was reached in Helgen auto save right after the character choice, so I decided to give it an evil playthrough. Well straight to the point that character never, ever got the letter from the DB courier, no matter what Ive done, different places to sleep, setting wait hours to 24, leaving stores, talking to Aventurs again... nothing. Ive spent several days figuring and nothing fixed but start another character.

Yup I did. I don't have any more of any such quest in my log. I also went back in to check back on him and the orphanage.

I can't start another character. I've progressed too much on Winterlyn. I am currently level 27 and done most of the other guild's quest chains.

You might just want to keep going with the character and not do the DB quest and save that for another character.

I had a level 37 character disappear from my savefiles when I started a new character. I now have a level 50 Mage and level 48 Master Craftsman.

You can start new characters. It's not that difficult. Even allows you to play differently to even be more suited to RP to the quests you want to do.