I'm a member of the TG, and I used to have a dialog option for the random encounter when a thief waylays you and asks for your valuables. Now that option isn't there anymore, and there is no choice but to handover or fight.
Anyone knows what happened? A glitch, or perhaps a consequence of a choice I made?

he doesnt like you anymore cuz he heard you were telling delvin that he isnt very good at stealing stuff. thieves are very sensitive folk.

When I'm a member of the thieves guild I get a new options to say, something about being a member and I can walk away without a fight.

What platform do you play on?

The thief hasnt been getting much business lately, so he couldnt give a dragon's fart about whether you're in the thieves guild or not

Wearing full nightingale armor makes thieves give u money

game isnt intelligent enough. its the same with stormcloaks and imperials. eg: you walk past imperials with stormcloak armor on, feck all happens. not a big deal though. game is still killer.

They're thieves. They make a career off of stealing from people. What do you expect?

He's an inept thief. Ra'kesh does not like inept thieves, especially ones that try to steal from him. Gives all thieves a bad name.

Lot's of non helpful replies.

People understand, read the post.

OP is saying when he was just a rank and file member of the guild he did get a dialogue option to say "I'm in the guild, jog on son".

But now he gets no such option and has to either cough up or throw down.

It happened to me too, when I became guild master... are you guild master OP?

It makes no sense and is very irritating, it needs fixing.

This. The A.I isn't really good