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I am new to LetsEncrypt and certs are not my forte in the first place. I am using certs for websites, RDP, and Exchange (Virtually all of my work is Windows based. I have attempted using several of the suggested/offered cmdlets and other then websites, there always seems to be a bug or catch that makes them not work. Is there any list or BBS of consultants that I can use to find a local consultant that can help, even on a paid basis? I just need to get this work and learn how to replicate the installs so I can get on with my real-world work!

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You don’t offer enough information about your specific problem, nor variables/circumstances, to allow someone to be sure that they can help you (paid or not).

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Maybe there should nonetheless be a list of consultants with their claimed expertise (although this is harder to maintain and vet than other community-maintained lists, like the web hosts list).

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I am working in all Windows. I use Server 2008 R2, Server 2012 R2, Server 2016 and now Server 2019. I have been able to get LetsEncrypt certs into IIS (I think it is V10). I m also running Exchange 2010 and soon Exchange 2016. I also run a fair number of servers providing RDP desktops. I need to setup SSL certs for all of these. I need to get standards for all three (3) that I can install and manage myself (Exchange does not change much). I have followed several of the provided scripts that I have found form people that offer help. All of them get part way through and run into issues. I need to get this done so I can move on with other issues.

It would be nice if there was a bulletin board somewhere consultants could post to and offer their services. I have found other specials this way (ex. router specialists) that have turned out very well. In view of all of the issues that I see with certificates (free and paid), and the need for them, I think there would be significant demand. I hope this help clarify my point.

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A few (free) pointers:

  • The default IIS that ships with 2008 R2 may not support hosting multiple domains on the same IP (SNI) - not sure if that is a requirement or not.
  • RDP requires “special” considerations and cert placement.
  • If you have an Active Directory, you might be able top leverage that “trust” for all your domain joined systems’ certs (IIS and RDP).
  • Exchange is a beast and quite difficult to setup and operate securely (without a dedicated admin); So I would recommend using any other SMTP system at the edge/border (as relays) to reduce the overall complexity, cost, and maintenance of your email system.

[But those are I just my “two cents”. For those that agree or disagree: This is not a debate, don’t take it there please. I’m merely throwing in “two cents” freely into this request and walking away.]

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Your response brings me critically to my point. This is an area of specialization all by itself. It would be great if there was a website that listed people that actually do it virtually DAILY that could offer their services tor those of us who need the service, but do not deal with it on a regular basis and do not have the time to learn a new vocation just to deal with this necessary evil!

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I do agree with you.
I just don’t know of such a place.
[and I really don’t think this is the place for that]

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I could not think of (or find) a better or more relevant place to post it. I could have sworn that I saw some suggestion of a site that had consultants listed when I first started playing with LetsEncrypt. but now that I am looking for it, I cannot locate it again! since the free Unix/Linux platforms seem to be the most popular, that is where most of the more hardened scripts seem to be. I would really like to find someone with experience on the Windows side?