Joseph C. “Joey” Meek Jr., 22, a friend of convicted mass-killer Dylann S. Roof, was sentenced today in U.S. District Court in Charleston by Judge Richard M. Gergel.

Meek faced a standard sentencing range of 27 to 33 months after pleading guilty last April to misprision of a felony and lying to federal investigators.

He was indicted in September 2015, three months after Roof went on a racially-motivated shooting spree, killing nine people on June 21 at the predominantly black Emanuel AME Church in downtown Charleston.

The sentencing judge said by not alerting authorities to Roof’s shooting plans, which the two had discussed during drug and alcohol binges in the weeks before the mass killing, Meek exposed the community to “extraordinary” danger.

“Certainly defendant’s failure to make an earlier report is tragic and deeply regrettable, but his failure to report was not a violation of federal criminal law,” the judge said in an order denying prosecutors attempts to give Meek a longer term, The New York Times reported.

Meek has sent handwritten letters of apology to the victim’s families, the newspaper reported. He also thinks about his friend’s killing spree everyday and has trouble sleeping.

“I truly in my heart didn’t take him seriously and I wish I would have,” Meek said at his sentencing hearing, the newspaper reported. “I didn’t believe he could do something so awful and cruel.”

Last December, Roof was found guilty of 33 charges, including federal hate crimes, for fatally shooting nine people he met on June 17, 2015, at a Bible study session at Charleston’s Emanuel AME Church. Roof hoped that his decision to kill the black worshippers would start a race war.

Baptized into the world of hate through the Internet, Roof was sentenced by the same jury in January to be executed for his murderous gun rampage.