I have a management server that uses dehydrated and a PowerDNS hook (tons of hooks available on GitHub) to generate wildcard certs. I have a cron job that runs a script to renew the wildcard, then pus

It's very good. I think the only thing that might need fixing is wildcard auto responders?

Yes, it will work if you regenerate the certificate and force the preferred chain to X1. Just switched mine to Sectigo since geocerts offered 1 year free wildcard cert, working well now.

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Update: They honored it and I got my free wildcard SSL.

I think I paid about $5 at gogetssl for a 1 year (non wildcard) Sectigo (Comodo) certificate. Iirc wildcards are abot $45 to $50/year.

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Not sure of any that are that cheap (other than Let's Encrypt for $0/year), but you should be able to find AlphaSSL or PositiveSSL wildcard via a reseller for $35-$50/year.

Anyone know where to buy something real cheap, like that $20/yr paid yearly (not 5 years) for a wildcard cert?

I'm using Let's Encrypt wildcard certs on my servers and they're working well.

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Totally Free for 1-yearRegularly $249 at PositiveSSL we're giving away wildcard SSL/TLS certificates for a very limited time.

PositiveSSL Wildcard was never that cheap, the cheapest was around $45 USD per year.