[Resolved] ERROR: Unable to start TLS: SSL connect attempt failed error:14090086

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L. Mark Stone
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Re: [Resolved] ERROR: Unable to start TLS: SSL connect attempt failed error:14090086

Postby L. Mark Stone » Tue Jun 02, 2020 12:06 am

So my blog post was for Gandi SSL certificates, but the methodology is still the same: If you have a third-party issuer, then you need their intermediate certificate.

Sounds like you found yours.

Mark


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Re: [Resolved] ERROR: Unable to start TLS: SSL connect attempt failed error:14090086

Postby maumar » Tue Jun 02, 2020 5:46 am

L. Mark Stone wrote:So my blog post was for Gandi SSL certificates, but the methodology is still the same: If you have a third-party issuer, then you need their intermediate certificate.

Sounds like you found yours.

Mark


Hello Mark
here in GOGETSSL they declare that zimbra needs a sha1 chain cert, this one:

Code: Select all

    Data:
        Version: 3 (0x2)
        Serial Number: 1 (0x1)
        Signature Algorithm: sha1WithRSAEncryption
        Issuer: C = GB, ST = Greater Manchester, L = Salford, O = Comodo CA Limited, CN = AAA Certificate Services
        Validity
            Not Before: Jan  1 00:00:00 2004 GMT
            Not After : Dec 31 23:59:59 2028 GMT
        Subject: C = GB, ST = Greater Manchester, L = Salford, O = Comodo CA Limited, CN = AAA Certificate Services
        Subject Public Key Info:
            Public Key Algorithm: rsaEncryption
                RSA Public-Key: (2048 bit)


Someone at Gogetssl support dept. wrote me this:

Code: Select all

As your certificate is old ( issued in 2017) you need to reissue your order to get updated files.
Process the reissue and try to use the bundle for installation together with added SHA-1.


this is the AAA cross signing provided by Sectigo for older devices
here:
https://support.sectigo.com/Com_Knowled ... 00000117LT

"For the vast majority of use cases Sectigo’s standard root supplies the full required client support. For unusual cases, Sectigo offers a new cross signing option with its AAA root, which does not expire until 2028."

Code: Select all

The first cert of the GOGETBUNDLE is
Certificate:
    Data:
        Version: 3 (0x2)
        Serial Number:
            93:8b:b0:8e:62:98:7b:4f:75:f9:8c:b6:a5:04:5c:96
        Signature Algorithm: sha384WithRSAEncryption
        Issuer: C = US, ST = New Jersey, L = Jersey City, O = The USERTRUST Network, CN = USERTrust RSA Certification Authority
        Validity
            Not Before: Sep  6 00:00:00 2018 GMT
            Not After : Sep  5 23:59:59 2028 GMT
        Subject: C = LV, L = Riga, O = GoGetSSL, CN = GoGetSSL RSA DV CA

you receive it with your cert or you can download here
https://www.gogetssl.com/wiki/intermedi ... tificates/
https://www.gogetssl.com/wiki/intermedi ... tificates/
https://gogetssl-cdn.s3.eu-central-1.am ... e-sha1.txt
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Re: [Resolved] ERROR: Unable to start TLS: SSL connect attempt failed error:14090086

Postby 6125amartin » Tue Jun 02, 2020 1:57 pm

L. Mark Stone wrote:
6125amartin wrote:This is likely due to the Sectigo root CA expiring yesterday:
https://www.reddit.com/r/sysadmin/comme ... y_morning/

Removing the following line from /etc/ca-certificates.conf does NOT appear to resolve the problem for Zimbra (tested on Ubuntu 18.04):
<pre>sed -i '/mozilla\/AddTrust_External_Root.crt/d' /etc/ca-certificates.conf</pre>

Please advise on how Zimbra can be updated to handle expiration of this Sectigo root CA. Thanks!


Just did a blog post on this:

https://www.missioncriticalemail.com/20 ... tallation/

Hope that helps,
Mark


Thank you Mark!
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Re: [Resolved] ERROR: Unable to start TLS: SSL connect attempt failed error:14090086

Postby Al-MacLean » Tue Jun 02, 2020 2:39 pm

Just did a blog post on this:

https://www.missioncriticalemail.com/20 ... tallation/

Hope that helps,
Mark


Thanks Mark! :D
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Re: [Resolved] ERROR: Unable to start TLS: SSL connect attempt failed error:14090086

Postby L. Mark Stone » Tue Jun 02, 2020 2:39 pm

A lot of the tech support folks at certificate issuer help desks don't understand that Zimbra needs the complete certificate chain to function.

Yes, web browsing will work, because the browsers all ship with many root and intermediate certs, so for a typical Apache/WordPress or similar web server installation, you need only tell your web server about your server certificate and your private key.

But Zimbra keeps several different keystores (no surprise, there are more than 80 different Open Source softwares in Zimbra, plus all of the Zimbra-provided code...), and those keystores as I understand it need the complete Root > Intermediate(s) > Server certificate chain on their own.

My customers yesterday with expired Sectigo intermediate certs? If Zimbra was still running, the web browsers accessing the Zimbra web UI showed no SSL issues. Why? Because the server certificate was still valid, and the browser was able to build a complete chain of trust between the certs already in the browser's own certificate store, plus the Zimbra-provided (still valid) server certificate.

Hope that helps,
Mark
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Re: [Resolved] ERROR: Unable to start TLS: SSL connect attempt failed error:14090086

Postby cyber7 » Wed Jun 03, 2020 5:28 am

L. Mark Stone wrote:A lot of the tech support folks at certificate issuer help desks don't understand that Zimbra needs the complete certificate chain to function.

Yes, web browsing will work, because the browsers all ship with many root and intermediate certs, so for a typical Apache/WordPress or similar web server installation, you need only tell your web server about your server certificate and your private key.

But Zimbra keeps several different keystores (no surprise, there are more than 80 different Open Source softwares in Zimbra, plus all of the Zimbra-provided code...), and those keystores as I understand it need the complete Root > Intermediate(s) > Server certificate chain on their own.

My customers yesterday with expired Sectigo intermediate certs? If Zimbra was still running, the web browsers accessing the Zimbra web UI showed no SSL issues. Why? Because the server certificate was still valid, and the browser was able to build a complete chain of trust between the certs already in the browser's own certificate store, plus the Zimbra-provided (still valid) server certificate.

Hope that helps,
Mark


The problem here is, Mark, that you are not seeing the entire picture. Other things are getting broken in the process, i.e. "opendkim". This could render all your mail as "SPAM" at companies like google, live, yahoo and many more. So, not only did they (Comodo) not notify their customers, but also exposed them to be blacklisted world-wide...

just my 10c
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Re: [Resolved] ERROR: Unable to start TLS: SSL connect attempt failed error:14090086

Postby maumar » Wed Jun 03, 2020 6:59 am

Just this morning, another server stopped with same issue, same err message
This is a wildcard cert and bundle is different. It was issued on April, but is should be reissued, just reissued, concatened AAA crossing signe chain cert and voila' all is ok


Code: Select all

/opt/zimbra/bin/zmcertmgr verifycrt comm ../commercial/commercial.key commercial.crt commercial_ca.crt
** Verifying 'commercial.crt' against '../commercial/commercial.key'
Certificate 'commercial.crt' and private key '../commercial/commercial.key' match.
** Verifying 'commercial.crt' against 'commercial_ca.crt'
Valid certificate chain: commercial.crt: OK



Bundle follows

Code: Select all

-----BEGIN CERTIFICATE-----
MIIF1zCCA7+gAwIBAgIRAJOLsI5imHtPdfmMtqUEXJYwDQYJKoZIhvcNAQEMBQAw
gYgxCzAJBgNVBAYTAlVTMRMwEQYDVQQIEwpOZXcgSmVyc2V5MRQwEgYDVQQHEwtK
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VQQDEyVVU0VSVHJ1c3QgUlNBIENlcnRpZmljYXRpb24gQXV0aG9yaXR5MB4XDTE4
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IXnjEeWrFvAZQhk=
-----END CERTIFICATE-----
-----BEGIN CERTIFICATE-----
MIIFgTCCBGmgAwIBAgIQOXJEOvkit1HX02wQ3TE1lTANBgkqhkiG9w0BAQwFADB7
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-----END CERTIFICATE-----
-----BEGIN CERTIFICATE-----
MIIEMjCCAxqgAwIBAgIBATANBgkqhkiG9w0BAQUFADB7MQswCQYDVQQGEwJHQjEb
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-----END CERTIFICATE-----
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Re: [Resolved] ERROR: Unable to start TLS: SSL connect attempt failed error:14090086

Postby maumar » Wed Jun 03, 2020 7:03 am

Further inspection:
unzipping Gogetssl bundle

Code: Select all

unzip _xxx_it.zip
Archive:  _xxx_it.zip
  inflating: _xxx_it.crt
  inflating: USERTrust_RSA_Certification_Authority.crt
  inflating: AAA_Certificate_Services.crt
 


As you can see, they provide you with the new USERTrust_RSA_Certification_Authority and the cross AAA
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Re: [Resolved] ERROR: Unable to start TLS: SSL connect attempt failed error:14090086

Postby Bittone » Wed Jun 03, 2020 10:10 am

Hello everyone,
I have the very same problem of the expired cert.
After activating the workaround I have a problem deploying the new ca_bundle.
After downloading from my issuer website the new bundle I tested it with zmcertmgr verifycrt and everything seems fine.

Code: Select all

[zimbra@postino commercial]$ ls -la
total 28
drwxr-x---. 2 zimbra zimbra    72 Jun  3 11:53 .
drwxr-x---. 5 zimbra zimbra    64 Jul 11  2016 ..
-rw-r-----. 1 zimbra zimbra 12078 Jun  3 11:53 commercial.crt
-rw-r-----. 1 zimbra zimbra  1734 Jun  3 11:53 commercial.key
-rw-r-----. 1 zimbra zimbra  9831 Jun  3 11:56 commercial_ca.crt
[zimbra@postino commercial]$ zmcertmgr verifycrt comm ./commercial.key ./commercial.crt ./commercial_ca.crt
** Verifying './commercial.crt' against './commercial.key'
Certificate './commercial.crt' and private key './commercial.key' match.
** Verifying './commercial.crt' against './commercial_ca.crt'
Valid certificate chain: ./commercial.crt: OK


But when I try to install them I get:

Code: Select all

[zimbra@postino commercial]$ zmcertmgr deploycrt  comm                                                       
** Creating /opt/zimbra/ssl/zimbra/commercial/commercial.crt
** Creating /opt/zimbra/ssl/zimbra/commercial/commercial.key
** Creating /opt/zimbra/ssl/zimbra/commercial/commercial_ca.crt
** Verifying '/opt/zimbra/ssl/zimbra/commercial/commercial.crt' against '/opt/zimbra/ssl/zimbra/commercial/commercial.key'
Certificate '/opt/zimbra/ssl/zimbra/commercial/commercial.crt' and private key '/opt/zimbra/ssl/zimbra/commercial/commercial.key' match.
** Verifying '/opt/zimbra/ssl/zimbra/commercial/commercial.crt' against '/opt/zimbra/ssl/zimbra/commercial/commercial_ca.crt'
ERROR: Unable to validate certificate chain: /opt/zimbra/ssl/zimbra/commercial/commercial.crt: C = SE, O = AddTrust AB, OU = AddTrust External TTP Network, CN = AddTrust External CA Root
error 10 at 3 depth lookup:certificate has expired
C = US, ST = New Jersey, L = Jersey City, O = The USERTRUST Network, CN = USERTrust RSA Certification Authority
error 10 at 2 depth lookup:certificate has expired
OK
[zimbra@postino commercial]$ ls -la
total 28
drwxr-x---. 2 zimbra zimbra    72 Jun  3 11:58 .
drwxr-x---. 5 zimbra zimbra    64 Jul 11  2016 ..
-rw-r-----. 1 zimbra zimbra 12078 Jun  3 11:58 commercial.crt
-rw-r-----. 1 zimbra zimbra  1734 Jun  3 11:58 commercial.key
-rw-r-----. 1 zimbra zimbra  9747 Jun  3 11:58 commercial_ca.crt


As you can see the commercial_ca.crt has been replaced by the old one and I cannot complete the installation of the new ca_bundle.
Any ideas why I get this ? According to the manual the certs must be placed in /opt/zimbra/ssl/zimbra/commercial dir and that's exactly what I did but the bundle gets overwritten.

Zimbra version is 8.7.11 community

Thank you all for your attention


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Re: [Resolved] ERROR: Unable to start TLS: SSL connect attempt failed error:14090086

Postby L. Mark Stone » Wed Jun 03, 2020 6:03 pm

cyber7 wrote:
L. Mark Stone wrote:A lot of the tech support folks at certificate issuer help desks don't understand that Zimbra needs the complete certificate chain to function.

Yes, web browsing will work, because the browsers all ship with many root and intermediate certs, so for a typical Apache/WordPress or similar web server installation, you need only tell your web server about your server certificate and your private key.

But Zimbra keeps several different keystores (no surprise, there are more than 80 different Open Source softwares in Zimbra, plus all of the Zimbra-provided code...), and those keystores as I understand it need the complete Root > Intermediate(s) > Server certificate chain on their own.

My customers yesterday with expired Sectigo intermediate certs? If Zimbra was still running, the web browsers accessing the Zimbra web UI showed no SSL issues. Why? Because the server certificate was still valid, and the browser was able to build a complete chain of trust between the certs already in the browser's own certificate store, plus the Zimbra-provided (still valid) server certificate.

Hope that helps,
Mark


The problem here is, Mark, that you are not seeing the entire picture. Other things are getting broken in the process, i.e. "opendkim". This could render all your mail as "SPAM" at companies like google, live, yahoo and many more. So, not only did they (Comodo) not notify their customers, but also exposed them to be blacklisted world-wide...

just my 10c


Very interesting that DKIM is broken with expired intermediates, thanks. There's probably other functionality then that is broken as well.

All the best,
Mark
___________________________________
L. Mark Stone
Mission Critical Email - Zimbra VAR/BSP/Training Partner https://www.missioncriticalemail.com/
Zeta Alliance http://www.zetalliance.org/

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