Too often users have expected library authors to support obsolete, insecure browsers along with the other maintenance and innovation work they are doing.
Now you're in a situation where you can start applying pressure to force change, since your tooling no longer supports your current environment. That would never have happened if Tailwind just kept paying your costs.
As a dev in the government sector, working for a large public agency, that's pretty much our attitude to IE 11. I mean, sure, staff in our agency need to keep it around for some legacy apps that haven't yet been migrated or replaced, but its being phased out and we're not supporting it beyond making sure that we detect it and put up a banner explaining that its not supported for some of our current (internal and external) apps.
In my bubble, there's no alternative right now. Switching to a more modern browser requires an enormous amount of agility throughout the pipeline that does not exist. To adopt a shiny new browser, agencies would need to push browser updates to all their client machines every ~4-6 weeks [2]. Solution providers need to perform continuous testing on their web apps (browser vendors do not guarantee minor updates are backwards compatible), creating patches, which need to be submitted to the government for regression testing... and oops that took too long and the next EOL is here.
With Microsoft's surprise obsolescence of Internet Explorer 11 across all its cloud offerings 1Q 2021, we're headed straight into a brick wall. Very interested to see what shakes out here.
I suspect initially we'll see the government just deploy and use older unsupported copies of Chrome/Edge browser, under the guise of "well it's better than IE11 right?". Longer term, ...?
[1] https://blog.tailwindcss.com/tailwindcss-v2#incompatibility-...
[2] Vendors do not support these versions after EOL for any reason. Firefox has an ESR branch, bless them, but some agencies have now increased scrutiny of Mozilla software for recent political/security reasons.