Former White House senior adviser David Axelrod said in June he was unaware Hillary Clinton conducted business from a personal email server when she served as secretary of State – but a State Department document dump Tuesday evening raises questions about how much he knew.

Asked last month in an interview whether he knew anything about Clinton's "homebrew" system when they worked together in the Obama administration, Axelrod responded, "I didn't know."

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However, correspondences from 2009 show that Axelrod may have had reason to know about Clinton's questionable email behavior. While it's possible Axelrod may not have been aware that Clinton was using a private server, he contacted her at least once with a "get better" note at one of her private email addresses.

Evidence of this begins with an email from Clinton's chief of staff, Cheryl Mills, dated June 8, 2009.

"Axelrod wants your email – remind me to discuss with you if I forget," Mills wrote.

Clinton responded that same day, writing, "Can you send to him or do you want me to? Does he know I can't look at it all day so he needs to contact me thru you or Huma or Lauren during work hours."

On June 23, 2009, Axelrod wrote Clinton a note, addressing it to one of her private email address, hdr22@clintonemail.com.

He wrote, "I have hesitated to email because I'm sure you are being inundated with good wishes. But I just wanted to tell you how sorry I was to hear about your injury." Clinton had just fractured her right elbow after a fall.

"It sounded horribly painful. I hope you will allow yourself to rest and recover. You are an all-star player, and we need you for the long run," the former White House senior adviser wrote.

Clinton responded from her private address, writing, "Thank you for your too kind words which were a greatly welcome addition to my healing and rehab. My word of advice is to watch where you step and stay grounded!"

"It's an honor to serve the President w you and I'd enjoy spending some one-on-one time just comparing notes and catching up in the next weeks," she added.

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Axelrod served as President Obama's senior adviser from 2009 to 2011. Clinton worked at the State Department from 2009 to 2013. During the entire time that she served at Foggy Bottom, she never once sent an official email bearing the standard @state.gov address.

Rather, she used a variety personalized email addresses, including hdr22@clintonemail.com and hrod17@clintonemail.com

Axelrod said in June that he would've have "asked questions" had he known about Clinton's questionable email behavior.

"I was there, I was the senior adviser. I didn't know that," Axelrod said in an interview on MSNBC, referring specifically to her private server. "I might have asked a few questions about it."