It is often claimed that Obi Wan Kenobi failed Anakin as a teacher because he was too lenient on him, focused too much on their brotherly relationship and let him get away with too much. However, I don't believe this can be supported by the movies nor the material in series like The Clone wars and even the novels. Quite the contrary in fact Obi Wan is strict as you can get. When his student so much as expresses an independent opinion or makes a suggestion, he's automatically shut down and told to keep in line. Obi Wan has not qualms about chiding Anakin in public, in a manner that comes over as demeaning and humiliating in front of people who are not Jedi. This image really is worth a thousand words. Anakin's whole stance screams of timidity, defensiveness and shame. He has his head down, his shoulders hunched and looks down. What was his crime? Suggesting that the Jedi should try to find Padme's assassin and not just protect her. In other words, take action to solve the problem instead of just waiting for it to happen again. Obi Wan clearly thinks the role of a father/mentor is to force his charge to be obedient. Or else. This is demonstrated by the when they go into the club to look for Padme's assassin in Attack of the Clones in which Obi Wan responds to Anakin telling him he seems him as a father by saying "then why don't you listen to me?". Anakin clearly feels he cannot confide in his Master from the outset. People often blame Anakin for this, saying its his fault for not trusting Mr Perfect. In Attack of the Clones, when the subject of his dreams about his mother is approached, Anakin quickly changes the subject saying "He would rather dream about Padme". This is an evasion, and when a young person is as evasive as this there is almost always a good reason for it. This type of evasion usually results from a person feeling ashamed or scared of opening up about a particular subject or event. Why would Anakin feel scared or ashamed of talking about his mother? Especially of his dreams she was in danger? I can only think of one explanation. He'd been scolded every single time he mentioned her. He'd been shamed for missing her. He'd been hit on the proverbial head with the Jedi Code and told his feelings are wrong Obi Wan tells him "dreams pass in time". It was already established that Anakin had prophetic dreams and premonitions. He had them even as a child on Tatooine. Qui Gon recognized this, called it "Jedi senses" so its obvious that Anakin's dreams are not just dreams. Hence, what Obi Wan was doing here was actually a form of gaslighting. We also see him gaslighting Anakin only a moments later in which he questions his Jedi senses, namely his ability to sense whether or not something is wrong in Padme's room. His senses prove to be as keen as his Master's, as he "feels it too" at the same time as him. Actually, this is gaslighting on two levels, as the ability to sense whether their charge might be in danger is accepted by Obi Wan as legitimate for a Jedi. Yet Anakin's sense that his mother might be in danger is obviously not. Regardless of whether Obi Wan believes Anakin's dreams are prophetic or not, he has no right to deny or invalidate Anakin's perception of reality. Anakin is regularly shamed or judged for his feelings and emotions, being told to "mind them" or reminded of the prohibition on attachments. For all that some fans say Anakin should have opened up to Obi Wan about his relationship with Padme because he too had a romantic relationship, they seem to forget how the one exchange they did have ended. With Obi Wan telling him not to allow things to go beyond friendship, because Jedi Code. It is obvious then that opening up about the true nature of their relationship (i.e telling him they were married) would not have ended well. Obi Wan would not have recognized or accepted their marriage, and would most likely have reported him to the Council and forced them to separate or divorce. Another example would be the deception Arc in the Clone Wars, in which Anakin was shamed by both Obi Wan and Yoda for feeling angry and upset, first at believing his Master was dead, and then for being lied to. Actually, this may have done more to destroy Anakin's faith in Obi Wan than anything else. If he could deceive him on such an important matter, why should he trust him and confide in him about anything? This also only served to reinforce the idea in Anakin's mind that when there was a conflict, Obi Wan would always side with the Council. Which was almost always the case. Even when it came to Ahsoka, even though Obi Wan claimed he did not support her expulsion we don't actually see him expressing vocal opposition to the Council's judgement on this matter. Obi Wan never once expresses praise, encouragement or validation for his Padawan when he does a good job or gets something right. Believe it or not. this does happen. The first and indeed only time we ever see him saying anything positive about Anakin to his face is towards the end of Revenge of the Sith when he's leaving for Utapua. This is actually quite shocking. In 13 years Obi Wan only praised Anakin once. This is the man who saved his life, who fought alongside him and had been one of the most capable commanders in the Clone Wars. Even on this occasion, the praise was preceded by Anakin admitting his faults and showing a deferential attitude. Tragically, the only time we ever see Obi Wan saying he loves Anakin was after their duel on Mustafar, and then he speaks in the past tense. He loved him. In all of their years together, for all their supposed friendship and camaraderie he never once said this. Never once offered Anakin any kind of validation or emotional support. I don't know if anyone on here has a background in teaching or childcare, but if they do they might see the problem with this. Any teacher who thought their main role was to force their students to be obedient, never gave them praise for good work and humiliated them in public would not be a good, nor indeed a competent teacher. It is not a teacher's role to break their student's spirit or control them, as Obi Wan seems to think is his role with Anakin. I believe on this basis that Anakin turning to Palpatine was not surprising at all. Its stated I believe in Canon that Padme was the only person that Anakin felt he could be himself around. Palpatine, sadly, was the only person he felt he could speak to and confide in without being judged, condemned or told his feelings were bad and wrong.