From his computer in Toronto, he sparked an explosion in the Iranian blogosphere through his online criticisms of his native country's government and his detailed instructions on creating blogs in Farsi.
When he later appeared to renege on some of his former convictions, openly defending the regime in Tehran, his followers were divided, with some in the online world expressing surprise and disdain for his apparent change of heart.
Now, news that Hossein Derakhshan may face execution has set the blogosphere on fire as supporters around the world ramp up efforts to save him.
Mr. Derakhshan, 35, has been jailed in Iran since November 2008. Over the summer, he was tried on charges of creating propaganda against the regime and insulting religious leaders, but the verdict is unclear.
On Tuesday, his supporters and human rights organizations said prosecutors had asked for the death penalty in his case. A judge has yet to rule on the request, they said, but they fear the sentence could be carried out soon.
"From what I understand, sentences like that could be handed down at any time," said Arnold Amber, president of Canadian Journalists for Free Expression. "It could be imminent, or it could be eight or nine months."
He said the jailed blogger's brother had been in touch with the organization to confirm that the prosecutor had requested the sentence.
Mr. Derakhshan, who went by the online handle Hoder, moved to Canada from his native Iran in 2000. He gained notoriety through his provocative political musings, including blog posts from a trip to Israel that lauded that country's political system in contrast with Tehran's theocracy.
He also instructed others on loading Farsi script onto Blogger, causing a surge in Iranian blogging that by some estimates saw as many as 60,000 blogs created and earned him the nickname "blogfather."
Within a few years, however, he seemed to soften on the Iranian regime, writing posts that supported Iran's right to develop nuclear weapons.
In 2008, he returned to his home country and was arrested shortly afterwards. This sparked an international campaign - promoted through blogs in English and Farsi, and Facebook - to secure his release. Human rights organizations joined them, calling on the Canadian government to get Mr. Derakhshan out of jail.
Mr. Amber said the Iranian government has been known to respond to diplomacy and pointed to the case of Maziar Bahari, an Iranian-Canadian reporter for Newsweek who was released from an Iranian prison after U.S. Secretary of State Hillary Clinton lobbied for his freedom.
Spokespeople for the Department of Foreign Affairs and International Trade could not be reached late Tuesday night.
The website kamtarin.com, a news website run by Iranians overseas, posted an interview with Mr. Derakhshan's mother, who described her son's listlessness in prison.
"He seems really depressed. He is really tired of being in limbo, being in jail, and being alone for two years. He says he spends most of the day sleeping," Ozra Kiarashpour told the site. "He recently requested to at least be transferred to the general ward but instead they agreed to move him to a different and better room, and potted a rose plant for him."
Ms. Kiarashpour said she visits her son weekly and that, before he returned to Iran, officials had told him he would not have any problems. Referencing his pro-regime blog posts, she lamented the fact that a prosecutor would want to make an example out of her son after he appeared to renege on his former criticisms.
"He is someone who repented and returned to serve his country and is ready to criticize his past thoughts and actions. Are you making an example to prove to people that repenting is useless? To show that supporting the ruling system will have this outcome?" the site quoted her as saying.