AOL Mail — long the clunky digital turf of lame dads, clueless grandparents, and  anyone weirdly nostalgic for 1998 — is gearing up for a major "refresh," or so said CEO Tim Armstrong at yesterday's UBS Media & Telecommunications conference. 

As Capital New York reports, Armstrong was asked how he plans to address the fact that using AOL mail isn't regarded as especially, err, hip in 2013. His answer:

“I would [pause] that issue is a brand issue and it is a product issue,” Armstrong responded. “Rehabbing the AOL brand and the AOL products is a very, very important project at the company, and it has my full attention,” he added, noting that a significant AOL email refresh was coming.

That puts AOL in a curious position not dissimilar from where Yahoo! Mail found itself before its recent redesign kerfuffle. Let's state the obvious: longtime users of both mail products aren't especially concerned by the cool factor — they're sticking around because of familiarity, and because changing your email address is a bit of a hassle. By going too far with its facelift in October, Yahoo! rather alienated that core constituency

By Wednesday, more than 3,000 people had signed a petition on Change.org to bring back the old Yahoo mail. A Facebook group called “Yahoo’s New Mail Fail” had nearly 500 members. A number of blogs were blasting the changes. And tens of thousands of users had posted to a Yahoo Mail forum to complain about the second update to Yahoo Mail in less than a year.

But AOL brings plenty of experience to the table: it has already redesigned its mail product a number of times, all without breaking free of the musty nineties CD-ROM smell. The most recent switch-up arrived just last summer, when a Senior VP at the company announced that they "did an in-depth ethnography study where we went into actual users’ homes"; the result was a "cleaner"-looking interface that moved the ad bar to the right side of the page and was shortly followed by the Alto web app.

Half a decade before that, the mail service was redesigned to look about like this:

Credit: VentureBeat

Critics promptly pointed out that the then-new look was a dead-ringer for Yahoo!, as it appeared in 2007:

Wrote Web expert Michael Arrington on his popular TechCrunch blog: "Internally, I'm hearing AOLers refer to the new portal as 'the Yahoo Portal,' although its official name is AOL 3.0."

Even officially, AOL is copping to the likeness. "Generally speaking, all portals provide a basic set of features and functionality (mail, news, weather, local information) so similarities are inevitable," an AOL spokesperson told OnlineMediaDaily.

Hence the paradox: launch a subtle redesign, and nothing really changes. Unveil a more drastic overhaul, and you risk scaring away the loyal fans or being called a copycat. But in the end, neither one will make people flock to your service if the service part isn't right.

And it's not like AOL doesn't have a loyalty corner. And as Ben Smith pointed out in 2011, it's not just the retro grandmas rocking the AOL look, but also some rather successful (and, okay, usually middle-aged) media and politics types who can't be bothered to migrate over to Gmail because, frankly, they don't need to worry about being judged.

For most tech companies, you'd think counting Matt Drudge, Arianna Huffington, and David Axelrod among your users would be a bragging right. For AOL, it's a sign that those big-name figures don't care enough about your complaining to switch to something else.