How do I request more than one certificate from Let's Encrypt?

[senseivita]

When the request is made, how do I list a second (and third, and so on) domain in it? There's only a single field. Do I use commas? semicolons? spaces? (,/;/ )

I'm already using dns-01, it's kind of a must because of the reverse proxy, I only would like to know which is the right separator. (Please.)

I've abstained from a wildcard because when I've tried setting wildcards on Exchange Server in the past it flipped on me — specifically for SMTP. So I figured it was some sort of an SMTP rule. The docu does mention wildcard certificates though, that would be enough to clear things up* if these certificates weren't used for the API as well.

Now, I wait.
Thanks.

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*: whether it's a Exchange-specific requirement or an SMTP+TLS requirement

 

[Stoiko Ivanov]

Would not have heard that SMTP has any issue with wildcard certificates (and know of a few deployments which use them)

Apart from that - why not simply add the other domain-names in the GUI (click on 'Add' above the table with the domains)

I hope this helps!

 

[senseivita]

That is… uh… I feel so stupid.

I guess it never occurred to me that the domain name for the cert could not not match the gateway's hostname even though in hindsight it was exactly what I was asking for (so stupid x2)

As for the wildcards, I'm not surprised this is a Microsoft-exclusive nonsensical limitation, it's kind of its ethos. The good thing in any case is that thanks to SPF records, it's not like there can be a laundry list of domains involved anyway, I was told on the Cloudflare console that my email may fail because I had 10+ entries on my SPF record — maybe. I don't remember if mx a ptr right after v=spf1 are entries or syntax but so far no bounces. Of course the only message I've sent this year was to a Yahoo! spamcatcher account for testing, and that thing will accept anything.

Sorry for taking this long, the message got buried under gray mail. Thanks for your help!