cannot get IOS or MacOSX to connect to dovecot:995 since upgraded Mac or iPhone
Versions:
[wls@www.wls.org]$ uname -a Linux www.wls.org 3.10.0-1160.119.1.el7.x86_64 #1 SMP Tue Jun 4 14:43:51 UTC 2024 x86_64 x86_64 x86_64 GNU/Linux [wls@ww.wls.org]$ dovecot --version 2.2.36 (1f10bfa63)
My Certs:
Testing cert dovecot.key unable to load certificate 139668060415888:error:0906D06C:PEM routines:PEM_read_bio:no start line:pem_lib.c:707:Expecting: TRUSTED CERTIFICATE lrwxrwxrwx 1 root root 21 Mar 25 15:44 dovecot.key -> dovecot.key.old_sep_2
Testing chain dovecot.pem SHA1 Fingerprint=4A:29:34:1D:D5:9C:67:59:FA:31:7E:FF:F4:53:F8:DB:25:73:15:07 subject= /OU=IMAP server/CN=imap.example.com/emailAddress=postmaster@example.com issuer= /OU=IMAP server/CN=imap.example.com/emailAddress=postmaster@example.com serial=C8AA4C688A3F2638 b5bd7939 notBefore=Sep 2 20:17:33 2018 GMT notAfter=Sep 2 20:17:33 2019 GMT lrwxrwxrwx 1 root root 21 Mar 25 15:44 dovecot.pem -> dovecot.crt.old_sep_2
New Certs:
Testing key ca.key.3.13.4 RSA key ok lrwxrwxrwx 1 root root 31 Mar 13 14:14 ca.key.3.13.4 -> ../../tls/private/ca.key.3.13.4
Testing chain ca.crt.3.13.4 SHA1 Fingerprint=79:69:88:2A:E0:BF:58:A8:21:E3:88:12:8D:45:20:4F:FD:68:33:63 subject= /C=XX/ST= /L= /O= /OU=IMAP server/CN=imap.example.com/emailAddress=postmaster@example.com issuer= /C=XX/ST= /L= /O= /OU=IMAP server/CN=imap.example.com/emailAddress=postmaster@example.com serial=B912DD19FEDC441C 402b4e2a notBefore=Mar 13 20:02:58 2026 GMT notAfter=Mar 13 20:02:58 2027 GMT lrwxrwxrwx 1 root root 29 Mar 13 14:13 ca.crt.3.13.4 -> ../../tls/certs/ca.crt.3.13.4
They install OK, dovecot starts; but iPhone and mac cannot connect to pop3
Cannot get my iPhone or Mac to accept new certs from lets encrypt, et. al.
This is a new problem, started recently.
My existing cert expired in 2016
William
On 31/03/2026 09:33, Bill Scheding via dovecot wrote:
They install OK, dovecot starts; but iPhone and mac cannot connect to pop3
Cannot get my iPhone or Mac to accept new certs from lets encrypt, et. al.
This is a new problem, started recently.
My existing cert expired in 2016
Hi William.
Over the years Apple (and other companies) have implemented more restrictive constraints on certificates in the name of security.
A good starting point for creating certificates that Apple devices will accept is: https://support.apple.com/en-us/103769
If you are using certificates issued by your own CA, you'll also need to (a) import the CA cert into your devices, and (b) enable them in Certificate Trust Settings, before the device will accept the cert. (You shouldn't need to do anything special for certificates issued by Let's Encrypt.)
Hope that helps.
Nick.
participants (2)
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Bill Scheding
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Nick Tait