What was wrong with Clippy? Well, where to start. Microsoft's now-defunct digital assistant has long been a byword for disastrous software design, but it seems there are still new lessons to be learned from the anthropomorphic paperclip's demise. One problem identified in the recent documentary Code: Debugging the Gender Gap and reported by The Atlantic, is that Clippy was the product of an unthinkingly male environment.

Roz Ho, a former Microsoft executive who was at the company during Clippy's conception, said that early focus group feedback from female users on Clippy and other Office assistants was "kind of negative." In the documentary Ho says:

Most of the women thought the characters were too male and that they were leering at them. So we’re sitting in a conference room. There’s me and, I think, like, 11 or 12 guys, and we’re going through the results, and they said, ‘I don’t see it. I just don’t know what they’re talking about.’ And I said, ‘Guys, guys, look, I’m a woman, and I’m going to tell you, these animated characters are male-looking.’

According to The Atlantic, Ho goes on to note that in the end, Clippy's creators just ignored this feedback because it didn't fit with what they were expecting to hear.

Today's sexualized female assistants show we've not learned much

Although Clippy's implied sexuality was only a small part of what went wrong with the software, it's interesting to consider how little we've apparently learned from episodes like this. The latest crop of digital assistants like Apple's Siri and Microsoft's Cortana may not be leering and male, but they've certainly got their own gender issues.

While Clippy's personality was interfering and patronizing, Siri and Cortana are subservient to the point of creepiness, leading to accusations of latent sexism. Critics point out that these computer programs are marketed as real people, as real women, and they just happen to be unquestioning and compliant — implicitly confirming society's expectation of women.

As Jezebel's Isha Aran pointed out in 2013, the tech world has long cultivated "an inextricable link between feminine sexuality and technology" which is "indicative of some intense and harmful objectification of women." Aran points to sexist ads from the 60s as evidence, but it seems that not much has changed for the smartphone generation. A Microsoft ad from earlier this year compares both Cortana and Siri to girlfriends that users can choose between. Now even Clippy would have drawn the line there.