Server 2012 R2 certificate shows incorrect password, but will install with password in Windows 10

Question

Good afternoon, all!

I'm having a problem importing a PFX cert into a Server 2012 R2 machine. When I do the import it errors out on the password. However, if I try the installation with my Win 10 laptop, the password succeeds with no problem. It looks like the cert is valid, but someting in the 2012 R2 server is either broken or missing.

The cert is from GoDaddy and I'm building the .pfx using OpenSSL on Windows. Again, the cert seems to be fine as the password works either typed or copy/paste.

Has anyone run into this before or have any thoughts on why this might be happening?

Thanks to all for looking!

Gregg

UPDATE - I tried using Win64 OpenSSL 1.1.1s but with no success. Any ideas on possible variables to use building a CSR and PFX?

Thanks!

Answer 1

Hi,

Thank you for posting your query.

Kindly follow the steps provided below to resolve your issue.

Import the .pfx into a newer version of Windows (Like Windows 10 or 2016) . This is important. While you import process, mark the certificate as exportable. This allows you to export the certificate afterwards with the older Triple-DES-SHA1 algorithm or/and with no password to protect the key.

Go to this link for your reference and other troubleshooting procedures https://learn.microsoft.com/answers/questions/995232/password-incorrect-when-import-certificate-on-serv.html

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Answer 2

Hello GreggHughes-3883,

Thank you for posting in our Q&A forum.

The information in the similar threads seem to be able to explain the issue you mentioned.

And you can try the method (command) in the threads to import the certificate on Server 2012 R2.

"The password you entered is incorrect" when importing .pfx files to Windows certificate store
https://stackoverflow.com/questions/69343254/the-password-you-entered-is-incorrect-when-importing-pfx-files-to-windows-cer

Windows certificate import not accepting private key password
https://serverfault.com/questions/1097326/windows-certificate-import-not-accepting-private-key-password

Hope the information above is helpful.

Best Regards,
Daisy Zhou

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Answer 3

Good morning!

Building the .pfx and importing into Windows 10, then exporting with the private key and importing into Server 2012 R2 worked and the new cert is functioning.

Thanks to all!

G