Huckabone and her son said they worked for days to decipher instructions, juggle passwords and tinker with settings to access Huckabone’s new Yahoo account. They struggled to get help from Cox or Yahoo.

It was so frustrating that Huckabone considered giving up email. “I’ve felt like I can handle my life, but technology is an area that I just cannot manage,” she said.

We’ve probably all fought with unnecessarily complicated technology. Huckabone’s experience shows when companies fail to make the complex seem easy, it can drain our energy, time and confidence.

The saga ended happily. After I told Cox about her problems, a company executive and a technician visited Huckabone’s San Diego home last week.

Huckabone said she chatted with Cox chief operations officer Colleen Langner, who apologized to her, while the technician fixed Huckabone’s lingering problems with email on her iPad.

It didn’t have to be this maddening for Huckabone or other Cox customers dealing with the email changeover. Cox and Yahoo could have done more to automate the inbox swap and to spare customers from doing their own tech support, according to an executive for email provider Proton.

How an email swap become a nightmare

Internet providers like Xfinity, AT&T or Cox tend to hand out an email address like [email protected].

But most people now choose something like a Gmail, Apple, Yahoo or Outlook account, telecommunications analyst Craig Moffett said. Cox said a fraction of its 6 million customers actively use a Cox-provided email address.

Cox this year said it would transfer cox.net email to Yahoo. Old email addresses would still work but customers would access messages from Yahoo accounts.

Huckabone said she had no clue about the planned switch. (Cox said it emailed customers multiple times about the move. Huckabone said she didn’t see any messages.)

After another bridge player mentioned in April that she had trouble with her Cox email switch, Huckabone realized she had stopped getting messages in her Cox inbox.

She said she tried calling Cox customer service for help but was disconnected. When her son, Jeff Deiss, returned from a vacation, Huckabone told him she couldn’t use email anymore. Deiss stepped in.

“How hard can this be?” he thought. “It turns out it was pretty hard.”

From his home in the Bay Area, Deiss spent hours remotely accessing his mom’s computer to enter passwords for Cox and Yahoo and coached his mom through accessing texted codes to the mobile phone she struggles to see. He dug through online forums of other Cox customers for their email switch tips.

When Deiss hit a roadblock with another password to access Yahoo email on his mom’s Apple Mail software, they called a Yahoo customer hotline. They were told the line was only for people who paid for a Yahoo premium service.

Finally a “gem” of a Cox customer support person they remembered as Chelsea confirmed that Huckabone’s email successfully swapped to Yahoo. Deiss eventually got Huckabone’s email working on her Mac computer but not on her iPad.

This could have gone better

Bart Butler, Proton’s chief technology officer, said it’s challenging to move many email accounts at once. And it’s more complicated for people like Huckabone who use downloaded email software like Apple Mail or Mozilla’s Thunderbird.

But Butler said Cox and Yahoo could have done far more to route emails automatically, reset configurations for Apple Mail and copy data to Yahoo without people needing to do so much on their own. “Cox pushed this complexity onto their customers,” Butler said.

He also said it could have been simpler if Cox gave customers time to set up a new email address with any other company, and promised the old Cox accounts would forward emails automatically.

“We are sorry for the challenges Ms. Huckabone had with accessing her emails following the migration to Yahoo,” Cox said.

Cox said it was committed to helping customers through the Yahoo switch, including with problems configuring email software like Apple Mail. Cox customers can reach a representative for email migration support at 1-866-562-7250. There’s also a website about the Yahoo switch.

Yahoo said it will “continue working to minimize complexity and ensure transitions like this are a positive experience.” A Yahoo representative declined to give me the customer phone number for email changeover help and said irrelevant calls might flood the line. Yahoo has online support for Cox customers and other instructions.

Huckabone said she was grateful for the Cox house call but worried about people who don’t have a resolute son or The Washington Post for backup.

“Other people are not so lucky,” she said. “All of the hours and all of the anguish that individuals put into this when it was really [Cox’s] responsibility.”