With a wildcard SSL cert all subdomains of a domain would be covered by the single certificate.

Can you please tell me the cheapest place you can find WildCard SSL certificates? And when I install them (into IIS, for example) Would I need to add a cert for each subdomain or would I need to just

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You don't need a separate domain or subdomain per every thing that you self-host. E.g. things like tt-rss, Piwik and Owncloud can happily live on the same domain within their own subdirectories. Moreo

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I did the math and decided I would be the kind of person to easily exceed 10 single domain certs - self-host everything - hence a wildcard.

Comodo Positive SSL + Wildcard + SAN

Your budget is too much because you can very easily purchase wildcard ssl certificate at lowest price compared to your budget by finding cheap wildcard ssl certificate providers from here http://www.l

+1 for the Comodo Positive SSL Wildcard from GoGetSSL

You don't need to pay that much for a wildcard SSL, even EV is cheaper than that amount.

Comodo Positive SSL Wildcard at $58.62

$105 for 3-year wildcard from garrisonhost - the ssdvirt people, been around for years

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Free wildcard SSL

Yes, we provide wildcard ssl's free on the condition they're only used on our Phoenix or Netherlands VPS.

Would you still be up to provide the Free Wildcard cert for our main domain name ?

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I bought my 3-year wildcard SSL from @miTgiB (Hostigation) for $129.99 USD and am very happy with both service and price tag:

check https://www.ssls.com/domain-type/wildcard-ssl-certificates?gclid=CP_074qIjcgCFYKc2wody5gG4w

Your gonna have to raise your budget quite a bit to even be considered for SSL, let along a wildcard.