Counter Terrorism Police examined the mobile phones of Safaan Ali, 19, and Mohammed Shehzad, 21, to find a number of concerning materials, including guides on the manufacture of explosives.
Detectives also found video content and concerning conversations demonstrating the sharing of extremist content to influence others.
Following a lengthy and complex investigation, Ali and Shehzad were both charged with one offence of dissemination of terrorism publications contrary to Section 2 of the Terrorism Act 2006.
Ali was also charged with eight offences of possessing a document or record containing information likely to be useful to a person committing or preparing for an act of terrorism contrary to Section 58 of the Terrorism Act 2000.
The pair pleaded guilty when they appeared at Leeds Crown Court.
Ali was sentenced to three-and -a -half years in prison and Shehzad was sentenced to 15 months.
“The publications, documents and digital content recovered from Ali’s devices featured praise for violence and support for Daesh.
“Shehzad and Ali’s dissemination of video content shows not only their own deeply radicalised mind set, but that they were encouraging support for violent radical terrorism.
“All terrorist groups rely heavily on their propaganda being shared online where it is used encourage support for their extreme and dangerous views and actions.
“Tackling all forms of extremist material is an essential part of protecting the public, safeguarding those who may be vulnerable to dangerous influences and preventing offences that incite or encourage acts of terrorism.
“The issue of online radicalisation is a serious one, but it is one that the public can really help us with. I would urge anyone who sees anything online that is concerning, to report it."