NYT is a great example of this. It took me multiple attempts over a span of 2 days to cancel my NYT subscription. There have been a few times since then when I've been tempted to re-subscribe (their election results tools are great), but remembering how hard it was to unsubscribe, I don't think I'll go back.
I've had to cancel the Times a couple of times over the years. Telling them that I lost my job only got one offer to extend at a discounted rate. But what really worked well was this:
NYT: "Can I ask why you want to cancel your subscription?"
Me: "No."
It's not on their script, so the operator just took care of it immediately.
On the plus side, at least you can speak to a human being at the Times pretty quickly. Good luck getting through to anyone at the Albuquerque Journal in under three days ("It looks like you're calling from a cell phone. Let's continue this conversation by text!").
Whenever I subscribe to any service on Apple I will immediately unsubscribe. If I find myself wanting to use the service again after it expires it's a simple tap to resubscribe. I think I actually end up with more subscriptions this way, but at least I know I'm getting use out of all of them. I wish I could a similar setup for all subscription services.
In several cities where I've lived, your library card would grant you online access to dozens or hundreds of newspapers from around the world. Some you could even download to your iPad to read later.
If you change your address to an address in California you're given the option to cancel online.
If you subscribed with a credit card, did the option of chargebacks ever come up? (Asking because these sorts of situations seem perfectly in line for disputing with your credit card provider.)
The most recent time was with a company that wouldn't honor their refund policy. They were awfully rude over email so I made sure to take screenshots of the policy on their website in case they disputed the chargeback and/or changed the wording on their site. Turns out, there wasn't even an option to upload that information when I filed with my credit card, and I won the case without doing anything further.
It was more difficult for me to get reimbursed when I tried depositing $300 in a Chase ATM and then it crashed halfway through. But that just involved a 2 minute phone call to resolve
It took EIGHT MONTHS and SEVEN phone calls with my bank to get them to charge back. And haul fought me every step of the process when they're the ones that told me to go to my bank. U-haul went as far as to straight up lie to my bank. I'm surprised they didn't forge documents with all the shit they were trying
I had an Amazon subscription charge I could not track down for a year. Every month I would call Amazon, who's CSR couldn't find it, and then my bank to reverse the charge.
Found out I had Amazon Premier still signed up on Amazon IT. The card worked globally but subscriptions displayed locally.
The online subscription could only be cancelled by telephone, on a phone line with small and inconvenient windows of opportunity, with long waits. When you get through, you have the normal retention/upsell attempts, and then are told that it will take at least two months to process your cancellation, and that you will continue to be charged in the meantime.
It was easier to cancel my card, at which point they somehow managed to withdraw access as soon as the first billing failed.
He cancelled the newspaper subscription, and then told me that I was mistaken about no longer getting 1/2 off on the crossword puzzle subscription. I'd only go back to full price on that if I let it expire and then re-ordered. As long as I have the subscription on auto-renew and those payments go through, it will stay at 1/2 price.