Why is it such agony to change all my online passwords?

I shriek at the computer screen, “Why are you doing this to me?!”

I am on a quest to reset passwords on 50 websites. Why? Because of advice received from my busy out-of-town son who works in the computer field. On a recent rescue mission, he updates my router's firmware to foil Russian malware. "Pretty tame," he notes. "Not like the time they disabled your anti-malware program and copied your keystrokes." Then, his eyebrows arch in astonishment. "Mom! You haven't changed your e-mail password in over four years!"

When I confess to using the same one for my bank accounts and the Canada Revenue Agency, he reminds me of last year's hack which brought down the CRA website. "You need to create new passwords for all those sites. And don't use the CRA password anywhere else!"

I neglect to tell him I've been using a 10-year-old password on about 40 other websites. Why so many? Well, online shopping and technology sites account for 15, followed by travel, entertainment, household accounts, health records and logons for courses and newspapers.

In a burst of enthusiasm and ill-founded confidence, I begin to correct the error of my ways.

But confusion reigns when organizations such as Google and Apple span my PC, tablet and cell phone. Do I update the password on each device? Why does Apple think I've bought a new iPhone and iPad? Why does my browser keep remembering old passwords? And why do some websites hide their Change Password option?

When befuddled, I opt for the “Forgot your User ID?” and “Forgot your password?” options. Sometimes, I choose both and when that fails, I face a barrage of online security questions. A few times, I screw up the answers I created years ago and try to remember: “Did I use an initial cap on my father's middle name?” and “Did I describe both the make and the model of my first car?”

Hmmmm, I don’t remember a first pet. Maybe I chose my grandmother’s tabby that hunkered down under the wood stove in her 1950s kitchen? In a diabolical way, websites refuse to reveal which of the answers is incorrect. On the brink of surrendering to madness, I lift my gaze from my wearisome work to the world outside. Is that a red-tailed hawk flying toward my neighbour’s black walnut tree? Here comes another. Caw! Caw! Oh, huge black crows. Are they sending me the message, “Nevermore?” Because that’s exactly how I feel.

I postpone my plight in favour of Netflix.

A few days later, driven by my son's admonishment and stimulated by a serious mug of dark roast, I begin afresh. My eager albeit edgy fingers hover above the keyboard.

Thirty-five passwords to go.

More difficulties ensue. Damn! I’ve used that password before. And I can’t figure out why I had a CBC password. I realize I don’t care. A-ha! I don’t need Future Shop any more, just Best Buy. My account with a bedding store hits a snag. A day later, I notice its local store has closed. Problem solved. Then, after accessing a money-management site, I’m aghast at its imperceptible milky-green font. I fire off an e-mail decrying its lack of usability and request info on deleting my rarely used account. They respond acknowledging my concern and suggesting that a font change is unlikely. I follow their step-by-step instructions on opting out, but am stymied when the final step, the “Finish” button, does not appear.

Why is this so stressful?

Am I a senior struggling to cope in a millennial world?

I can't quit now, I’m more than half way. I resort to phone calls to navigate the road maps of puzzling websites. I share pleasantries with an IT specialist at one hospital, but the customer rep at another is gruff, especially when I call back. Hydro's Customer Care leaves a voicemail asking me to rate my recent experience. Hell, I don't even remember contacting them.

The pinnacle of my frustration occurs after I fail to access a website for the fourth time. With spiking blood pressure and bulging eyes, I glare at the sunflower-gold banner atop a “Customer Sign In” page. It taunts me. Indiscernible grey text on a white background forces me to seize a magnifying glass. The words “E-mail/Access ID” reveal themselves. Okay. Instead of entering the usual access ID, I'll try my e-mail address. Yikes! Shouldn't have done that! And now I can't contain my cursing as I read the screen's solemn response: “Your Sign-In ID has been suspended.”

Defeated, I scrutinize the site for a phone number. Emerging victorious, I dial. It’s after 5 on the night before a long weekend, but I am obsessed. I key in my identification number, press 1 for English and am rewarded with a live person. A wonderful live person!

After confirming my identity, she exhibits immense patience while unravelling my dilemma. Her company has three websites. I had created a new password on the wrong site. Later, when I insist there's a problem on one of their screens, she waits until I realize I've entered the wrong number in the wrong box. We laugh. Together, we create new passwords for the two websites I need. She waits while I bookmark them. I ask, "Can you please stay on the line while I print out the info I want?" Without a hint of impatience, she responds, "Of course." Before we part, she ensures I can access both sites. I am delighted. She has almost helped me overcome the past several days of futility and profanity.

Despite knowing that any site and anyone can be hacked, I feel a sense of achievement in creating unique passwords for all those damn websites. But one still eludes me.

It’s Uber. There’s no phone service. I need a millennial.