In AOTC, Obi-Wan knew Anakin was on Tatooine. And he was also aware of his dreams about his mother (which he seemed surprisingly disinterested in). Yoda also sensed tremendous pain in Anakin all the way on Coruscant. I get that they were pre-occupied with trying to prevent war and whatnot, but did anyone ever inquire Anakin about this? He would've undoubtedly pulled out his signature "I don't wanna talk about it" line, but that doesn't seem like something they would've glossed over. Is there an EU story I'm unaware of that touches on this? Your thoughts?
Anakin does tell Obi-wan and the Council that he went to Tatooine because of his mother. But it is apparent that he wasn't entirely truthful of what transpired. I'm not sure what's being said in the current EU, but in the old EU, it was something that was addressed a few times in the "Star Wars: Republic" monthly series.
"You were on Tatooine. What happened?" "Um...nothing." "Nothing at all?" "Um...yeah. Not a thing." "Didn't see anyone? Didn't do anything?" "Nope, not a thing." "What about your pain and anguish that we felt?" "Um...I stubbed my toe. It really hurt. Ouch!" "Well, okay then." "Thanks." "By the way, how's you Mom doing?" (Anakin kills everyone in the room.) "Any more questions?"
From what I remember, he only told them that he got to Tatooine due to his mother, and his pain was in relation to her death. The grisly details and the whole 'I slaughtered an entire camp down to the children' bit, he left aside. In one of the now not-canon comics, he did tell a Jedi exactly what had transpired (but not before trying to kill him first, of course, due to the Jedi being from a Tusken tribe.) The Jedi basically said, "I'll keep your secret, but you must owe up to your failures and report this to the Council -- this is your burden to bear." This Jedi would eventually become Darth Krayt which is...why he's no longer canon. To be honest, he never made much sense to me because it's like, "Oh, a fellow Jedi just went berserk and attacked me but I'll let it slide because he just told me of how he gave into his anger and wiped out an entire tribe of my own people for what they did to his mother." Then twenty years later he's all, "Raaagh! That punk kid became Darth Vader! I know, I'll become a Sith Lord because that'll totes solve everything!!" Yeeeah... really glad he's not canon anymore.
Yoda felt he was in terrible pain, which could easily be taken as the death of his mother. Yoda/Obi-Wan however should have been extremely remorseful that they held him back from going to help her. I think by the time the war was up and running, Anakin being rebellious and not following instructions for the millionth time was the least of their worries.
Considering what happened, it's incredible that the incident is not reflected on in the movies in any way afterwards. Whether and Anakin lied about it or the Jedi being either credulous or oblivious to it adds a certain specific dimension. But we are left to imagine what happened when different possible scenarios put a different complexion on what comes later.
I think that Obi-wan knew to an extent, but didn't pry. He seemed to know about Padme and didn't get involved. Obi-wan is so perceptive, I think he surely knew something. I bet he didn't want to pull that string, especially with the war going on. I think that is something Ob1 was saving for peace time to confront. One problem at a time.
So Anakin's path to the darkside was unchecked by those that should have know for the sake of discretion?
Obi-wan did it because he believed that she could be of help to him, in a way that he couldn't be. That's why he went to Padme's apartment before leaving for Utapau. OBI-WAN: "Has Anakin been to see you?" PADME: "Several times...I was so happy to hear he was accepted on the Jedi Council." OBI-WAN: "I know...he deserves it. He is impatient, strong willed, very opinionated, but truly gifted." PADME: "You're not just here to say hello. Something is wrong, isn't it?" OBI-WAN: "You should be a Jedi, Padme." PADME: "You're not very good at hiding your feelings." OBI-WAN: "It's Anakin...He's becoming moody and detached. He's been put in a difficult position as the Chancellor's representative...but I think it's more than that. I was hoping he may have talked to you." PADME: "Why would he talk to me about his work?" OBI-WAN: "Neither of you is very good at hiding your feelings either." PADME: "Don't give me that look." OBI-WAN: "I know how he feels about you." PADME: "What did he say?" OBI-WAN: "Nothing. He didn't have to." PADME: "I don't know what you're talking about." OBI-WAN: "I know you both too well. I can see you two are in love. Padme, I'm worried about him. I fear your relationship has confused him. He's changed considerably since we returned... Padme, I'm not telling the Council about any of this. I...I hope I didn't upset you. We're all friends, I care about both of you..." PADME: "Thank you, Obi-wan." OBI-WAN: "Please do what you can to help him." He had figured it out, but not how bad it was. Not that they were married and not that she was pregnant. It didn't happen overnight. It took a good long while and not too long ago, he tried to broach the subject, but Anakin kept lying to him and it was afterwards, that he finally figured it out.