An email released by WikiLeaks on Thursday provides new insight into Hillary Clinton’s carelessness with sensitive information in her emails and shows she was warned by close confidants to be more cautious — even long after leaving the State Department.

WikiLeaks released a 2014 email conversation between Clinton and her current campaign Chairman John Podesta about the tactical situation in Iraq and elsewhere in the Middle East.

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In what until today was the latest available email in the chain, Clinton stated that “there may be opportunities as the Iraqi piece improves.” She also asked Podesta if he had “any idea whose fighters attacked Islamist positions in Tripoli, Libya,” which was “worth analyzing for future purposes,” according to Clinton.

Podesta quickly recognized the conversation shouldn’t be happening on Gmail and Clinton’s “clintonemail” server. “Yes and interesting but not for this channel,” he warned.

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If Clinton was discussing information after leaving the State Department that was sensitive enough to give Podesta concern, one can only imagine the kind of information she was relaying to others.

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Another email dumped by WikiLeaks Thursday suggests Podesta was warned in 2008 about the dangers of communicating sensitive information on unsecured servers.

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“I was struck by the memo partly because it was first I had heard of it but much more because it was a sensitive doc bumping around on public email addresses,” Denis McDonough, President Obama’s first chief of staff, wrote to fellow transition team member Daniel Tarullo on Nov. 3, 2008, “There is a very real threat to the security of our documents,” he said.

Tarullo then added Podesta, also working for Obama’s transition team, to the email chain and McDonough warned Podesta directly, “I know I’m like a broken record on this, but I think we should arrange a briefing on the cyber threat for all associated with your effort. We have a real security threat on our stuff here.”