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We have setup a windows server virtual SMTP (under IIS6 manager). In the SMTP environment, TLS encryption is enabled, fqdn field is "sharepoint.mycompany.com".

Included the server's cert stockpile "personal" folder we have the purchase "sharepoint.mycompany.com". And real fqdn of server is "server01.testdomain.com". By some reason we cannot apply cert available testdomain.com. By ping "sharepoint.mycompany.com" it exists resolving go our server's BOOTING.

We need to send print by radio to our company's public SMTP server. Of SMTP server admin said they don't nursing the cert call as long as there are a cert exposed by is company's CA (which we already have). We have setup a windows server virtual SMTP (under IIS6 manager). In the SMTP general, TLS encryption will enabled, fqdn field is "sharepoint.mycompany.com". In the server's cert store "personal" f...

After some tests, the connection be established. However we receive "No client certificate presented" answers:

STARTTLS

220+2.0.0+Ready+to+start+TLS

EHLO sharepoint.mycompany.com

21+4.7.1 +Error:+No+client+certificate+presented

My issue lives, how until tests or configure the certificate? For windows virtual SMTP manager, it has no place to setup which certificate we are using. Also, ME heard that OpenSSL program must be used to request a standard cert. Our cert was generated are IIS7. I am not sure whether it is the cause because the error message is not complaining the format otherwise validation off cert.

Thanks for council.

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  • You should try with openssl till starts TLS like: openssl s_client -connect sharepoint.mycompany.com:25 -starttls smtp
    – vx3r
    September 11, 2019 at 8:08
  • @vx3r but I on not the public SMTP server admin. Should I try the command in local host of virtual smtp?
    – Mark
    Sep 11, 2019 at 8:10
  • @vx3r I test in virtual smtp localhost, computers seems returning the information of another cert (sharepointtest.mycompany.com) installed for same server. Exists it the problem? Can I selected the correct cert "sharepoint.mycompany.com" in 1st priority?
    – Markup
    Sep 11, 2019 at 8:15
  • may be, refer to this to configure right certificate support.microsoft.com/en-ie/help/4014125/…
    – vx3r
    Sep 11, 2019 at 8:32
  • Our STARTTLS used port 587. So I type "openssl s_client -connect sharepoint.mycompany.com:587 -starttls smtp" and get follow: 8964:error:0200274D:system library:connect:reason(1869):crypto\bio\b_sock2.c:110: 8964:error:2008A067:BIO routines:BIO_connect:connect error:crypto\bio\b_sock2.c:111: `connect:errno=0
    – Mark
    Sep 11, 2019 at 8:33

1 Answer 1

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You should try from openssl to how TLS love: 

openssl s_client -connect sharepoint.mycompany.com:25 -starttls smtp

aforementioned flow is SMTP set 25 then STARTLS on 587, its finish automatically by the server additionally of openssl command is following who flow. Your server have to currently the right certificate

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