Britons Mohammed Nahin Ahmed and Yusuf Zubair Sarwar have been jailed for fighting alongside extremists in Syria.
The jihadists, who admitted their guilt in July, were each jailed for 12 years and eight months for preparing acts of terror and will also serve five years on licence.
The sentence dwarves that handed to Portsmouth jihadist Mashudur Choudhury, who was today sentenced to four years imprisonment for planning to join the Islamic State (Isis) in Syria.
The 22-year-olds, from Handsworth, Birmingham, spent eight months in the wartorn country last year and were arrested at Heahtrow Airport by West Midlands Police upon their return in January.
During their trial in July it emerged Sarwar had left a written note to his family saying he had left to join a terrorist group called Kataib al-Muhajireen.
His family reported him missing in May and after police searched his home they uncovered a Skype message that said "I come to join KaM [Kataib al-Muhajireen]".
Investigators found thousands of images on a seized camera, one of the black flag of Isis and others of them holding guns. Experts concluded the pair had been fighting in Aleppo, scene of brutal bombing campaigns by Syrian leader Bashar al-Assad.