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I'm facing an issue when trying to send emails from SharePoint, I get one of the error messages below:

An operation failed because the following certificate has validation errors:
  Subject Name: CN=mailservername
  Issuer Name: CN=mailservername
  Thumbprint: 645B2D4B72573478DBD162F39AAE0260B25F6582
  Errors: SSL policy errors have been encountered.  Error code '0x6'..


An operation failed because the following certificate has validation errors:
  Subject Name: CN=mailservername
  Issuer Name: CN=mailservername
  Thumbprint: 645B2D4B72573478DBD162F39AAE0260B25F6582
  Errors: The root of the certificate chain is not a trusted root authority..


I have a single server farm, with SharePoint server 2016

When I configured the outgoing emails with the exchange server as provided by the IT team (mail.organizationname.gov.xx) or the server IP, I get the first error message.

When I configured it with the mail server name as mentioned in the error (either as is, or with domain (FQDM)) I get the second error !

Any help would be highly appreciated

Thank you


Edit: I'm sending the emails via PowerShell

  • have you checked Certificate store and this Certificate (with the Thumbprint) if the root is alright on Sharepoint servers? You probably need to install Root Certificate for him, or try to check this on the Mail Server – Zdeněk Vinduška Feb 18 at 8:42
  • @ZdeněkVinduška Thanks alot for your quick reply, As for the solution, to be honest certificates are not my thing, I'm not very familiar with them, can you further explain what to do ! is it the certlm.msc we are taking about ! and where to check the certificate – Shadi Mahasneh Feb 18 at 9:14
  • open mmc.msc then Add CTRL+M certificate store docs.microsoft.com/en-us/dotnet/framework/wcf/feature-details/… and find certificate with your thumbnail and check the Cert Path if Root Certificate is correct. support.nmi.com/hc/en-gb/articles/… – Zdeněk Vinduška Feb 18 at 9:43
  • @ZdeněkVinduška I've tried to find the certificate on the SP server, but it seems like it's not there, I don't have direct access to SMTP server since it's client environment. Note that another environment was working fine without any certificates ! – Shadi Mahasneh Feb 18 at 10:31
  • so maybe thats a restriction on SMTP server, contant your Exchange guys, they will probably know a solution – Zdeněk Vinduška Feb 18 at 10:47
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  1. You need to set SSL to Yes in Outgoing emails and Create TLS communication between SP and Exchange servers. Manual here. They're resolving the same issue with certificate in 2nd half of manual.

Hope it helps!

  • Thank you, I have requested the certificate and waiting their response, and I'll upvote your answer and select as an answer when verified – Shadi Mahasneh Feb 19 at 8:15
  • You're welcome. You can already upvote now for help :) – Zdeněk Vinduška Feb 19 at 8:22
  • I can't upvote you due to the lack of reputation, but I've selected your reply as an answer, ty – Shadi Mahasneh Feb 19 at 8:56
  • Ah, ok, you're welcome :) – Zdeněk Vinduška Feb 19 at 9:01
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Thanks to Zdeněk's answer, after referring to the article above, it turns out since I'm contacting the exchange server with TLS, the SendEmail via PowerShell won't work, and sending an email from SharePoint itself was already working, and I only tried PowerShell for testing purposes (Which I forgot to mention it in my question)

Thanks alot Zdeněk for your replies

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