On su, 06 syys 2020, Jochen Kellner via FreeIPA-users wrote:

Hello,

I'm running IPA on current Fedora 32, freeipa-server-4.8.9-2 and 
pki-server-10.9.0-0.4

Today the certificate of my IMAP server (running on Debian Buster) was
automatically refreshed:

,----
| Request ID '20181003215953':
|         status: MONITORING
|         stuck: no
|         key pair storage: 
type=FILE,location='/etc/ssl/private/imap.jochen.org.key'
|         certificate: type=FILE,location='/etc/ssl/certs/imap.jochen.org.crt'
|         CA: IPA
|         issuer: CN=Certificate Authority,O=JOCHEN.ORG
|         subject: CN=imap.jochen.org,O=JOCHEN.ORG
|         expires: 2022-09-07 09:30:16 CEST
|         dns: imap.jochen.org
|         principal name: imap/jupiter.jochen....@jochen.org
|         key usage: 
digitalSignature,nonRepudiation,keyEncipherment,dataEncipherment
|         eku: id-kp-serverAuth,id-kp-clientAuth
|         pre-save command:
|         post-save command: /root/refresh_cyrus_certificate.sh
|         track: yes
|         auto-renew: yes
`----

On an iPhone one of my users gets a message that the certificate is not valid.
Reason seems to be this: 
https://7402.org/blog/2019/new-self-signed-ssl-cert-ios-13.html

When I look at the certificate with openssl I see:

,----
|         X509v3 extensions:
|             X509v3 Authority Key Identifier:
|                 
keyid:4F:F8:45:3D:E8:06:4B:8D:BB:9D:D2:D1:8B:00:43:A1:07:16:A1:17
|
|             Authority Information Access:
|                 OCSP - URI:http://ipa-ca.jochen.org/ca/ocsp
|
|             X509v3 Key Usage: critical
|                 Digital Signature, Non Repudiation, Key Encipherment, Data 
Encipherment
|             X509v3 Extended Key Usage:
|                 TLS Web Server Authentication, TLS Web Client Authentication
`----

My current guess is that the "Key Usage: critical" is the reason for the iOS 
error.

I don't think so. Official Apple requirements state the following:
https://support.apple.com/en-us/HT210176

---------------------------------------------------
All TLS server certificates must comply with these new security
requirements in iOS 13 and macOS 10.15:

- TLS server certificates and issuing CAs using RSA keys must use key
  sizes greater than or equal to 2048 bits. Certificates using RSA key
  sizes smaller than 2048 bits are no longer trusted for TLS.

- TLS server certificates and issuing CAs must use a hash algorithm from
  the SHA-2 family in the signature algorithm. SHA-1 signed certificates
  are no longer trusted for TLS.

- TLS server certificates must present the DNS name of the server in the
  Subject Alternative Name extension of the certificate. DNS names in
  the CommonName of a certificate are no longer trusted.

Additionally, all TLS server certificates issued after July 1, 2019 (as
indicated in the NotBefore field of the certificate) must follow these
guidelines:

- TLS server certificates must contain an ExtendedKeyUsage (EKU)
  extension containing the id-kp-serverAuth OID.

- TLS server certificates must have a validity period of 825 days or
  fewer (as expressed in the NotBefore and NotAfter fields of the
  certificate).

--------------------------------------------------

Can you please show both your CA and the IMAP server public certificates
in their entirety?


--
/ Alexander Bokovoy
Sr. Principal Software Engineer
Security / Identity Management Engineering
Red Hat Limited, Finland
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