By Lily Rothman
March 3, 2015

Possible Presidential contender Hillary Clinton may have broken the e-mail rules during her time as Secretary of State, according to a new story in the New York Times. Clinton used her own personal e-mail account to conduct government business, the Times reports.

It’s not the first time Clinton’s e-mail has given her trouble — her use of personal e-mail accounts had been made public at least two years ago, but it was almost two decades ago she didn’t hide the fact that she was, as a TIME cover story about the then-First Lady put it, “computer illiterate.”

That particular story used the First Lady’s 50th birthday as a way to discuss the Baby Boom generation’s maturation: Clinton, newly an empty-nester, was re-examining her life and deciding where to go from there. One possible direction was online:

At the time, President Clinton said he imagined the couple retiring one day to sit on a beach as “old people laughing about our lives”; TIME commented that such a future was unlikely to satisfy his wife, who said that she would instead “go on to do something else that I find challenging and interesting.” Years later, there’s no doubt that she made good on that prediction. She may have even overcome her fear of computers. After all, by today’s standards when it comes to “Internet E-Mail,” most people in 1997 were pretty much dummies.

Read the 1997 cover story here, in the TIME Vault: Turning Fifty

Write to Lily Rothman at lily.rothman@time.com.

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