Zimbra Certbot LetsEncrypt - certificate and private key do not match

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1

My domain is: mail.avdenterprises.com

I ran this command:

/opt/zimbra/bin/zmcertmgr verifycrt comm /opt/zimbra/ssl/zimbra/commercial/commercial.key /opt/zimbra/ssl/letsencrypt/cert.pem

It produced this output:

** Verifying '/opt/zimbra/ssl/letsencrypt/cert.pem' against '/opt/zimbra/ssl/zimbra/commercial/commercial.key'
139684204856640:error:0607907F:digital envelope routines:EVP_PKEY_get0_RSA:expecting an rsa key:crypto/evp/p_lib.c:474:
ERROR: Certificate '/opt/zimbra/ssl/letsencrypt/cert.pem' and private key '/opt/zimbra/ssl/zimbra/commercial/commercial.key' do not match.

My web server is (include version): n/a

The operating system my web server runs on is (include version): Ubuntu Server 20.04

My hosting provider, if applicable, is: n/a

I can login to a root shell on my machine (yes or no, or I don't know): Yes

I'm using a control panel to manage my site (no, or provide the name and version of the control panel): No

The version of my client is (e.g. output of certbot --version or certbot-auto --version if you're using Certbot): certbot 2.0.0

I found a site: Certificate Key Matcher - Check whether your private key matches your SSL certificate.

Even though that site will expose my private key (re-ran the certificate issuance later) that site indicates my certificate and private key match so I believe, possibly, the error from certbot is misleading and/or mistaken.

Thanks for your help.

2

Which error from Certbot exactly? I only see a Zimbra command, not Certbot.

Also, could you please elaborate on how /opt/zimbra/ssl/zimbra/commercial/commercial.key and /opt/zimbra/ssl/letsencrypt/cert.pem were generated to begin with?

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Thanks for your reply Osiris. Here are the steps I took:

1.  sudo certbot certonly --preferred-chain "ISRG Root X1"

** change to root (use: su) **

2.  cp /etc/letsencrypt/live/mail.avdenterprises.com/privkey.pem /opt/zimbra/ssl/zimbra/commercial/commercial.key

3.  chown zimbra:zimbra /opt/zimbra/ssl/zimbra/commercial/commercial.key

4.  wget -O /tmp/ISRG-X1.pem https://letsencrypt.org/certs/isrgrootx1.pem.txt

5.  cat /tmp/ISRG-X1.pem >> /etc/letsencrypt/live/mail.avdenterprises.com/chain.pem

6.  cp /etc/letsencrypt/live/mail.avdenterprises.com/* /opt/zimbra/ssl/letsencrypt/

7.  chown zimbra:zimbra /opt/zimbra/ssl/letsencrypt/*

NOTE: Step 6/7 is necessary for proper permissions, otherwise it fails saying unable to read

** exit to zimbraadmin **

8.  ls -al /opt/zimbra/ssl/letsencrypt/   NOTE: Verify permissions

9. sudo /opt/zimbra/libexec/zmfixperms

** change to zimbra mail (use: sudo su zimbra -)

10. cd ~

11. /opt/zimbra/bin/zmcertmgr verifycrt comm /opt/zimbra/ssl/zimbra/commercial/commercial.key /opt/zimbra/ssl/letsencrypt/cert.pem /opt/zimbra/ssl/letsencrypt/chain.pem

NOTE:  Currently step 11 fails saying they do NOT match

12. /opt/zimbra/bin/zmcertmgr deploycrt comm /opt/zimbra/ssl/letsencrypt/cert.pem /opt/zimbra/ssl/letsencrypt/chain.pem

13. zmcontrol restart
4

On the error, I may have mispoken, it is probably a Zimbra error, not a certbot error. Thanks.

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Googling this lead me to a thread mentioning ECDSA keys. If I look at your certificate history at crt.sh | mail.avdenterprises.com your most recent certificates indeed have an ECDSA key, which has become the default for Certbot 2.0.0. I'm pretty certain your current cert and private key are ECDSA too.

I guess Zimbra doesn't like ECDSA keys. Please open a bug report at Zimbra for this :slight_smile:

Also note that you've issued many identical certificates already, which would lead to hitting a rate limit soon. Please be more careful.

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Unfortunately I cannot get it to work which is why there are so many duplicates. Is there a way to just remove them all and start fresh?

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The first one would have worked, as it's the only RSA cert :slight_smile: You might have gotten a different error, but that's in the past :man_shrugging:t2:

That wouldn't fix the problem of Zimbra not being able to handle ECDSA certificates. Check if you still have your old RSA cert around.

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No problem. Thanks for finding that thread! :slight_smile: I re-wrote the code in the zmcertmgr and now I am good to go. :slight_smile:

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9

Well, that's a solution too, one I like :smiley: Too bad Zimbra is Perl tho :cry:

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When it doesn't work, write the code yourself! :smiley: :slight_smile: Thanks!

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11

Yup! That's even true for Certbot :slight_smile: I run my own fork which has a few extra features/enhancements :slight_smile:

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