Openssl: Difference between revisions

Line 323: Line 323:
  echo -ne '\0username\0password'| base64
  echo -ne '\0username\0password'| base64
  AUTH LOGING output_of_that_echo
  AUTH LOGING output_of_that_echo
===server certificate does NOT include an ID which matches the server name===

Revision as of 16:23, 30 March 2022



Documentation and HOWTOs

Dovecot and ssl

Networksolutions certs: After creating myserver.key and myserver.csr and obtaining certs: (don't forget to insert newlines between the blocks!)

cat OV_NetworkSolutionsOVServerCA2.crt OV_USERTrustRSACertificationAuthority.crt AddTrustExternalCARoot.crt > intermediate.pem

In dovecot.conf:

ssl_cert_file = /usr/local/etc/IMAP.EXAMPLE.COM.crt
ssl_key_file = /usr/local/etc/myserver.key
#optional, only if you want to require client to provide cert
#ssl_ca_file = /usr/local/etc/intermediate.pem

Courier-imap and ssl

Networksolutions certs: After creating myserver.key and myserver.csr and obtaining certs: (don't forget to insert newlines between the blocks!)

cat AddTrustExternalCARoot.crt NetworkSolutions_CA.crt > intermediate.pem
cat myserver.key >> IMAP.EXAMPLE.COM.crt

In imapd-ssl:


Network Solutions certificates bundle


cat OV_NetworkSolutionsOVServerCA2.crt OV_USERTrustRSACertificationAuthority.crt AddTrustExternalCARoot.crt > intermediate.txt


Comodo bundle order

COMODORSAOrganizationValidationSecureServerCA. + COMODO rsa add trust ca ( + addtrustexternalcaroot )

Generate a signing request

openssl req -nodes -newkey rsa:2048 -keyout my.domain.key -out my.domain.csr

The resulting csr is the signing request, my.domain.key is the private key you save not readable for anyone but root!


Create private key (using config file)

openssl req (-config /etc/pki/tls/ -newkey rsa:2048 -nodes -keyout domain.key

Create CSR using config file

openssl req -config /etc/pki/tls/ -new -newkey rsa:2048 -nodes -keyout -out

Convert der to pem

openssl x509 -inform der -in certificate.cer -out certificate.pem

Creating CSR for multiple hosts

For example

Remove password from private key

Examining certificates

openssl verify cert.pem
openssl x509 -in cacert.pem -noout -text
openssl x509 -in foo.pem  -inform pem -noout -text 
openssl rsa -noout -text -in server.key
openssl req -noout -text -in server.csr
openssl rsa -noout -text -in ca.key
openssl x509 -noout -text -in ca.crt

with expiration date:

openssl x509 -noout -text -enddate -in ca.crt
  1. to check CN
openssl x509 -in server.crt -noout -subject
openssl pkcs12 -info -in keyStore.p12
openssl pkcs12 -info -in keyStore.pfx

Checking a service

  1. Note -CApath should point to your local collection of public CA certs
openssl s_client -connect -CApath /etc/ssl/certs host:pop3 -starttls pop3
openssl s_client -port 443 -CApath /etc/ssl/certs -host -prexit
openssl s_client -connect -starttls imap
openssl s_client -connect web.server:443 -showcerts
openssl s_client -connect -servername

Just check expiration date:

 openssl s_client -connect -starttls imap 2>/dev/null | openssl x509 -noout -dates


Check your site


echo quit | gnutls-cli --starttls-proto smtp --port 25 servac.skk | grep Status
echo quit | gnutls-cli --port 465 servac.skk | grep Status

check if certs match

TODO: -clr_check too

openssl pkey -in privateKey.key -pubout -outform pem | sha256sum 
openssl x509 -in certificate.crt -pubkey -noout -outform pem | sha256sum 
openssl req -in CSR.csr -pubkey -noout -outform pem | sha256sum

These values show match Also:

openssl verify -CAfile ca-bundle foo_bar.crt

A script to do these checks: [sslcheck]

Creating your own CA and signing with it

(based on

cd /etc/ssl
mkdir newcerts
(perform secret rituals)


Order of certificates in bundle

Root CA comes last

using s_client

no client certificate sent

try adding -cert


Secure Renegotiation IS NOT supported

Probably using wrong TLS version

Can't use SSL_get_servername

Try using hostname instead of IP address


server reset the connection

unable to load client certificate private key file

Verification error: unable to verify the first certificate

problem missing CA cert

error 20 at 0 depth lookup: unable to get local issuer certificate

you probably need to provide the right -CAfile maybe self signed?


Verify return code: 21 (unable to verify the first certificate)

Probably requires bundle


Bad certificate (code 42)

Means the server demands you authenticate with a certificate, and you did not do so, and that caused the handshake failure.


check certificate chain

openssl s_client -connect -showcerts


Some of the output

Certificate chain

0 s:CN = foo.local
  i:CN = foo.local-CA

0: first in chain

s: subject  ( openssl x509 -noout -in foo.crt -subject )

i: issuer ( openssl x509 -noout -in foo.crt -issuer )

check expiration date

echo | openssl s_client -servername NAME -connect HOST:PORT 2>/dev/null | openssl x509 -noout -dates


139814102202256:error:0906D06C:PEM routines:PEM_read_bio:no start line:pem_lib.c:707:Expecting: TRUSTED CERTIFICATE

i've seen this happen when someone deleted the BEGIN/END CERTIFICATE lines

or a file is in DER format

SSL CTX certificate file error: error:0906D06C:PEM routines:PEM_read_bio:no start line




check if webserver supports old tls

openssl s_client -connect -tls1
openssl s_client -connect -tls1_1

or when vhost:

 openssl s_client -servername -connect -tls1_1


ERROR: Certificate verification: Not trusted

seems to be an lftp issue

unsupported certificate purpose



ssllabs checks

Chain issues: Incorrect order, Contains anchor

Could be the topmost cert in the bundle provided, try removing it


Chain issues: Contains anchor

Seems to mean there's a root ca in the bundle

check smtp submission

echo -n "username" | base64
echo -n "password" | base64
openssl s_client -connect -starttls smtp -crlf




echo -ne '\0username\0password'| base64
AUTH LOGING output_of_that_echo

server certificate does NOT include an ID which matches the server name