His third album, Yasteseryal, was released in 2005. The release of this album coincided with elevated political tension in Ethiopia surrounding the Ethiopian general election, 2005. His politically and socially inspired songs acted as a call for unity and peace and made the 17 years of TPLF-led government in power concerned. Consequently the government banned four songs including "Yasteseryal" from playing on radios and TV. The most popular song of the album "Yasetseryal" claims that there is no real change in Ethiopia but a new government and the Tigray People's Liberation Front (TPLF) fight against the Derg was nothing but an infamous military junta. The album sold more than a million copies within a few months after its release, becoming the biggest selling Ethiopian music album to date.
His fourth and most recent studio album, Tikur Sew, was released in 2012. Its lead single Tikur Sew, which is the namesake of the album, hailed Ethiopia's Emperor Menelik II as a champion for all African people, citing his feat of leading the Ethiopian people to victory at the Battle of Adwa. Being aware of the atrocities committed by Menelik during his reign as Emperor against various ethnic groups in Ethiopia, especially the Oromo, Tewodros tried to appeal to an audience among the Oromo people by mentioning and acclaiming Oromo generals who participated in the war. He also wrote some of the lyrics for the song in Afaan Oromoo. Nevertheless, the song was made part of the controversy surrounding the celebration of the 100th year anniversary of Menelik's death in December 2013. As a result, Heineken's sponsorship of Afro's concert tour prompted a boycott of Heineken products among Oromo people. Heineken dropped Teddy's tour sponsorship.
Afro was accused of hit-and-run manslaughter and was imprisoned in April 2008. Some sources claimed that the accusation was politically motivated, following the release of several songs critical of the government, especially during the May 2005 national election. Afro pleaded not guilty to these allegations, and his court case and imprisonment were national talking points in Ethiopia. Some members of the opposition viewed his imprisonment as part of the regime in Ethiopia attack on symbols of Ethiopian unity. Afro was convicted of manslaughter on 5 December 2008 and the judge sentenced him to six years' imprisonment and a fine of 18,000 Birr (apr. 1800 USD). On 18 February 2009, Afro's prison sentence was reduced from six years to two years by an appellate court. On 13 August 2009, Afro was released from prison eight months early on account of good behaviour in prison.