SSL/TLS Option Breaks My SMTP Notifications
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Certificate trust issue?
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I dont think so as I have a storage server that has a notification screen that looks just like the pfsense screen except no STARTTLS option and using the options that do not work for pfsense work for that server as in
mail server local IP
port 465
SSL/TLS
login
from same as login
to addressit is using a different login, but everything else is the same
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By the way thank you all for helping me try to figure this out
soon I may give up and just not use SSL/TLS to secure the connection since its only internal and not an external connection
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I dont think so as I have a storage server that has a notification screen that looks just like the pfsense screen except no STARTTLS option and using the options that do not work for pfsense work for that server as in
mail server local IP
port 465
SSL/TLS
login
from same as login
to addressit is using a different login, but everything else is the same
Just because some other system trusts the certificate doesn't mean pfSense does.
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If your mail server is on your LAN, and you trust other devices on the same LAN, you should be fine using a non-TLS/SSL (465) and/or submission (587).
Just send to the "25" port.
Of course, all the rest will be a pure postfix-setup-issue. -
I deleted and re-added my email accounts on mt ipad and was able to use TLS on those devices successfully.
I am trying to check the cert to make sure that is not it, anyone know the quickest way to test the cert postfix is using?
My imap-ssl is not showing any issues with the cert it uses.
Also getting some new log info when testing settings last night, will post when I start testing again.
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Using http://www.checktls.com/ it seems to show the cert is validated and OK and was able to use TLS 1.2 successfully for the connection.
Master.cf
smtp inet n - n - - smtpd -v
submission inet n - n - - smtpd -v
-o smtpd_tls_security_level=encrypt
# -o smtpd_tls_security_level=may
# -o smtpd_sasl_auth_enable=yes
# -o smtpd_client_restrictions=permit_sasl_authenticated,reject
# -o milter_macro_daemon_name=ORIGINATING
smtps inet n - n - - smtpd -v
-o smtpd_tls_wrappermode=yes
# -o smtpd_sasl_auth_enable=yes
# -o smtpd_client_restrictions=permit_sasl_authenticated,reject
# -o milter_macro_daemon_name=ORIGINATINGUsing 25 or 465 with no SSL/TLS or STARTTLS option checked works
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It doesn't matter what any thing else thinks of the cert. pfSense has to trust it.
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It doesn't matter what any thing else thinks of the cert. pfSense has to trust it.
Ok, then how will I know as the cert and postfix settings have not changed since my last alert email, i see nothing in the logs showing cert issues with pfsense 192.168.1.1
pfsense logs show this error over and over
php-fpm /system_advanced_notifications.php: Could not send the message to gmail.com – Error: could not start TLS connection encryption protocol
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The two places I know of for the CA to be located in pfSense are:
- System / Certificate Manager / CAs
- /usr/local/share/certs/ca-root-nss.crt
This is not to say there couldn't be some other location. These are just the two I'm aware of.
I am also not sure in which of the locations it is required to be for notifications. Mine is in both. But I'm thinking it probably has to be in ca-root-nss.crt. -
Did you have to hand edit ca-root-nss.crt to add the CA?
The two places I know of for the CA to be located in pfSense are:
- System / Certificate Manager / CAs
- /usr/local/share/certs/ca-root-nss.crt
This is not to say there couldn't be some other location. These are just the two I'm aware of.
I am also not sure in which of the locations it is required to be for notifications. Mine is in both. But I'm thinking it probably has to be in ca-root-nss.crt. -
Yes, I just added it below all the other CA's and incremented the number of certificates.
Mine is a self signed, so I have to added it. I wish PHP curl could use it from the one that is in config (System / Certificate Manager / CAs) so it would survive upgrades and I wouldn't have to remember to add it to the file.
Here are the results of notification test message with and without and with my CA added to the ca-root-nss.crt file.
Aug 2 23:47:48 php-fpm 42511 /system_advanced_notifications.php: Message sent to xxx@yyy.com OK Aug 2 23:47:06 php-fpm 11699 /system_advanced_notifications.php: Could not send the message to xxx@yyy.com -- Error: could not start TLS connection encryption protocol -
According to a kdiff comparison it appears this certificate was present in 2.3 but is absent in 2.3.2. If that is the CA for your cert then that would likely be why it quit working.
/usr/local/share/certs/ca-root-nss.crt
Certificate: Data: Version: 3 (0x2) Serial Number: 36 (0x24) Signature Algorithm: sha1WithRSAEncryption Issuer: C=FI, O=Sonera, CN=Sonera Class1 CA Validity Not Before: Apr 6 10:49:13 2001 GMT Not After : Apr 6 10:49:13 2021 GMT Subject: C=FI, O=Sonera, CN=Sonera Class1 CA Subject Public Key Info: Public Key Algorithm: rsaEncryption Public-Key: (2048 bit) Modulus: 00:b5:89:1f:2b:4f:67:0a:79:ff:c5:1e:f8:7f:3c: ed:d1:7e:da:b0:cd:6d:2f:36:ac:34:c6:db:d9:64: 17:08:63:30:33:22:8a:4c:ee:8e:bb:0f:0d:42:55: c9:9d:2e:a5:ef:f7:a7:8c:c3:ab:b9:97:cb:8e:ef: 3f:15:67:a8:82:72:63:53:0f:41:8c:7d:10:95:24: a1:5a:a5:06:fa:92:57:9d:fa:a5:01:f2:75:e9:1f: bc:56:26:52:4e:78:19:65:58:55:03:58:c0:14:ae: 8c:7c:55:5f:70:5b:77:23:06:36:97:f3:24:b5:9a: 46:95:e4:df:0d:0b:05:45:e5:d1:f2:1d:82:bb:c6: 13:e0:fe:aa:7a:fd:69:30:94:f3:d2:45:85:fc:f2: 32:5b:32:de:e8:6c:5d:1f:cb:a4:22:74:b0:80:8e: 5d:94:f7:06:00:4b:a9:d4:5e:2e:35:50:09:f3:80: 97:f4:0c:17:ae:39:d8:5f:cd:33:c1:1c:ca:89:c2: 22:f7:45:12:ed:5e:12:93:9d:63:ab:82:2e:b9:eb: 42:41:44:cb:4a:1a:00:82:0d:9e:f9:8b:57:3e:4c: c7:17:ed:2c:8b:72:33:5f:72:7a:38:56:d5:e6:d9: ae:05:1a:1d:75:45:b1:cb:a5:25:1c:12:57:36:fd: 22:37 Exponent: 65537 (0x10001) X509v3 extensions: X509v3 Basic Constraints: critical CA:TRUE X509v3 Subject Key Identifier: 47:E2:0C:8B:F6:53:88:52 X509v3 Key Usage: Certificate Sign, CRL Sign Signature Algorithm: sha1WithRSAEncryption 8b:1a:b2:c9:5d:61:b4:e1:b9:2b:b9:53:d1:b2:85:9d:77:8e: 16:ee:11:3d:db:c2:63:d9:5b:97:65:fb:12:67:d8:2a:5c:b6: ab:e5:5e:c3:b7:16:2f:c8:e8:ab:1d:8a:fd:ab:1a:7c:d5:5f: 63:cf:dc:b0:dd:77:b9:a8:e6:d2:22:38:87:07:14:d9:ff:be: 56:b5:fd:07:0e:3c:55:ca:16:cc:a7:a6:77:37:fb:db:5c:1f: 4e:59:06:87:a3:03:43:f5:16:ab:b7:84:bd:4e:ef:9f:31:37: f0:46:f1:40:b6:d1:0c:a5:64:f8:63:5e:21:db:55:4e:4f:31: 76:9c:10:61:8e:b6:53:3a:a3:11:be:af:6d:7c:1e:bd:ae:2d: e2:0c:69:c7:85:53:68:a2:61:ba:c5:3e:b4:79:54:78:9e:0a: c7:02:be:62:d1:11:82:4b:65:2f:91:5a:c2:a8:87:b1:56:68: 94:79:f9:25:f7:c1:d5:ae:1a:b8:bb:3d:8f:a9:8a:38:15:f7: 73:d0:5a:60:d1:80:b0:f0:dc:d5:50:cd:4e:ee:92:48:69:ed: b2:23:1e:30:cc:c8:94:c8:b6:f5:3b:86:7f:3f:a6:2e:9f:f6: 3e:2c:b5:92:96:3e:df:2c:93:8a:ff:81:8c:0f:0f:59:21:19: 57:bd:55:9a SHA1 Fingerprint=07:47:22:01:99:CE:74:B9:7C:B0:3D:79:B2:64:A2:C8:55:E9:33:FF -----BEGIN CERTIFICATE----- MIIDIDCCAgigAwIBAgIBJDANBgkqhkiG9w0BAQUFADA5MQswCQYDVQQGEwJGSTEP MA0GA1UEChMGU29uZXJhMRkwFwYDVQQDExBTb25lcmEgQ2xhc3MxIENBMB4XDTAx MDQwNjEwNDkxM1oXDTIxMDQwNjEwNDkxM1owOTELMAkGA1UEBhMCRkkxDzANBgNV BAoTBlNvbmVyYTEZMBcGA1UEAxMQU29uZXJhIENsYXNzMSBDQTCCASIwDQYJKoZI hvcNAQEBBQADggEPADCCAQoCggEBALWJHytPZwp5/8Ue+H887dF+2rDNbS82rDTG 29lkFwhjMDMiikzujrsPDUJVyZ0upe/3p4zDq7mXy47vPxVnqIJyY1MPQYx9EJUk oVqlBvqSV536pQHydekfvFYmUk54GWVYVQNYwBSujHxVX3BbdyMGNpfzJLWaRpXk 3w0LBUXl0fIdgrvGE+D+qnr9aTCU89JFhfzyMlsy3uhsXR/LpCJ0sICOXZT3BgBL qdReLjVQCfOAl/QMF6452F/NM8EcyonCIvdFEu1eEpOdY6uCLrnrQkFEy0oaAIIN nvmLVz5MxxftLItyM19yejhW1ebZrgUaHXVFsculJRwSVzb9IjcCAwEAAaMzMDEw DwYDVR0TAQH/BAUwAwEB/zARBgNVHQ4ECgQIR+IMi/ZTiFIwCwYDVR0PBAQDAgEG MA0GCSqGSIb3DQEBBQUAA4IBAQCLGrLJXWG04bkruVPRsoWdd44W7hE928Jj2VuX ZfsSZ9gqXLar5V7DtxYvyOirHYr9qxp81V9jz9yw3Xe5qObSIjiHBxTZ/75Wtf0H DjxVyhbMp6Z3N/vbXB9OWQaHowND9Rart4S9Tu+fMTfwRvFAttEMpWT4Y14h21VO TzF2nBBhjrZTOqMRvq9tfB69ri3iDGnHhVNoomG6xT60eVR4ngrHAr5i0RGCS2Uv kVrCqIexVmiUefkl98HVrhq4uz2PqYo4Ffdz0Fpg0YCw8NzVUM1O7pJIae2yIx4w zMiUyLb1O4Z/P6Yun/Y+LLWSlj7fLJOK/4GMDw9ZIRlXvVWa -----END CERTIFICATE----- -
Great! Thank you all for your help! I will add the CA for the current cert from the mailserver and post if the issue is resolved.
@NOYB - another thing I noticed that the standard web interface cert is shown as OK in firefox while chrome throws the caution error, any way to correct this as I have not had any luck getting a cert for just the IP anymore, used to but have not be able to recently. Alt would be to use the domain name, but I find the IP more reliable.
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Yes, I just added it below all the other CA's and incremented the number of certificates.
Mine is a self signed, so I have to added it. I wish PHP curl could use it from the one that is in config (System / Certificate Manager / CAs) so it would survive upgrades and I wouldn't have to remember to add it to the file.
Here are the results of notification test message without and with my CA added to the ca-root-nss.crt file.
Aug 2 23:47:48 php-fpm 42511 /system_advanced_notifications.php: Message sent to xxx@yyy.com OK Aug 2 23:47:06 php-fpm 11699 /system_advanced_notifications.php: Could not send the message to xxx@yyy.com -- Error: could not start TLS connection encryption protocolThanks NOYB, this was very useful information for me.
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@NOYB - another thing I noticed that the standard web interface cert is shown as OK in firefox while chrome throws the caution error, any way to correct this as I have not had any luck getting a cert for just the IP anymore, used to but have not be able to recently. Alt would be to use the domain name, but I find the IP more reliable.
I imported my own self-signed cert and the CA for it (System / Certificate Manager / …). Then configured Admin Access to use that cert for SSL and installed the CA in my browsers trusted roots.
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I filed a ticket for this issue:
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I filed a ticket for this issue:
Thank you. Sure hope someone can fix that. Sure would be a big help.
