Conversation so far:
What were some of Anwar al-Awlaki's connections?
As imam at a mosque in Falls Church, Virginia, Anwar al-Awlaki spoke with and preached to three of the 9/11 hijackers.
What countries was Anwar Al-Awlaki going after?
Anwar Al-Awlaki was active in the United States, United Kingdom and Yemen.
Were there others connected to Anwar Al-Awlaki?
Anwar al-Awlaki may have associated with Umar Farouk Abdulmutallab, who attempted the 2009 Christmas Day bombing of an American airliner. Al-Awlaki was allegedly involved in planning Abdulmutallab's attack.
How was Anwar Al-Awlaki contacting these people?
Charles Allen, U.S. Under-Secretary of Homeland Security warned that Anwar al-Awlaki targets U.S. Muslims with radical online lectures encouraging terrorist attacks from his new home in Yemen.“
Did any of Anwar Al-Awlaki's connections report him?
Sharif Mobley had acknowledged contact with Anwar al-Awlaki. The Mobley family claims the contact was for spiritual guidance in further studies of Islam.
Was Anwar Al-Awlaki prosecuted for it?
Prosecutors could not charge Anwar al-Awlaki when he returned from a trip abroad, because a 10-year statute of limitations on lying to the Social Security Administration had expired.
What happened after Zachary Adam Chesser was arrested?
After pleading guilty to aiding al-Shabaab, Zachary Adam Chesser was sentenced in federal court on February 24, 2011 to 25 years in prison.

Question: Did Anwar contact him again after that?
Self-contained rewrite: Did Zachary Adam Chesser contact him again after reading Anwar al-Awlaki's teachings?