- Default to an automatic resubscription for (say) 50-75% of the current list price
- Consent to OAuth2<->Google ("one-time blahblahblah"), and retrieve perpetual payment info that way
- Accept Store receipts (capturing all email headers and keeping all PDFs for cross-comparison... meh)
I wonder if you should send 2 warning emails or 3. ("action required" "your account will automatically be subscribed unless...")
This is maybe a gray-ish pattern, but would convert some percentage of users to a higher ongoing subscription level. This sounds like a line-of-business type extension, so that percentage may be marginally appreciable.
Perhaps combat the boringness aspect of the store-receipt process by sending solicitation emails ASAP to get that rolling.
And, hrm, anticipate refunds. :(
It would be a lot better if they would allow us to contact our users via email. Instead, we're going to have to use pop-up messages that annoy users and are likely to be reflexively closed by many of them.
I'd love to know what they are communicating to users, and when. At least then we could wait to communicate with them until just after they send an email, so that users would be less likely to ignore our messages. As is, it feels like we're flying blind.
Thinking about it, it's not really on point for Google™©® to connect you with your customers; your outreach could be considered unsolicited and G could be argued to be enabling spam. What a wonderful situation G has dug for itself here.
The only thought I can come up with is to partially break or otherwise "wait what"-ify your extension's behavior to concretely capture users' attention. You mentioned it does PDF processing of some kind; a relevant example in this case could be injecting new page(s) into generated output (or watermarking, but that may be mechanically trickier, and my knee-jerk connection to watermarking could wind up being "meep, this software has just gone rogue on me" - and depending on my stress level I may not actually read any notices).
Said injected (or overlaid) content would likely immediately first clarify that visiting the options page and clicking a giant green button will 100% revert functionality. It would probably also do well to include a website name (also showing a giant banner), a contact email address (RIP in advance), and possibly a suggestion/invitation to forward the PDF to internal IT for review in case of doubt (which would neatly offload some % of "???" to external labor that is incidentally highly trusted, but may look odd).
FWIW, I noticed the latest versions of Chrome have redesigned the extension UI; overflow icons have moved from the system menu into a dedicated popup. Some users (Windows) likely have this update, while others (eg, myself using Chromium 83.0/Debian, and version-locked enterprise users) don't. So hypothetical screenshots would need to illustrate both flows.
Besides all that, auto-renewing to some (non-low-end, because why not) percentage of the current list price, and straightforwardly handling refunds, seems to be the only obvious fallthrough I can see.