After enabling SSL in CentOS 6/Postfix/Dovecot, certain mail server SMTP “connection timeout”

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Extending the title:
After enabling SSL encryption I have no problems sending emails from client (Thundirbird) and webmail (Horde and Squirrelmail) to all servers I tried like gmail, hotmail, yahoo and others.

The exception is, at least for now, protonmail.com

Postfix has mail to send them in queue (24 hours +).



Oct 6 20:00:37 host postfix/smtp[15295]: connect to mailsec.protonmail.ch[185.70.40.102]:25: Connection timed out
Oct 6 20:00:37 host postfix/smtp[15295]: A71AA1CA1A17: to=<fff@protonmail.com>, relay=none, delay=6199, delays=6139/0.05/60/0, dsn=4.4.1, status=deferred (connect to mailsec.protonmail.ch[185.70.40.102]:25: Connection timed out)


The issue is also sending mail from protonmail.com to my mail server.

This happens also only with this mail server.

I have a undelivered message source I got from the sender.




Diagnostic-Code: X-Postfix; Host or domain name not found. Name service error for name=myDomain.com type=MX: Host not found, try again




nslookup -type=mx myDomain.com



Server: 127.0.0.53

Address: 127.0.0.53#53

Non-authoritative answer:

myDomain.com mail exchanger = 5 mail.mailServer.com.




telnet mailsec.protonmail.ch 25 



Trying 185.70.40.102...

Connected to mailsec.protonmail.ch

Escape character is '^]'

Connection close by foreign host




 netstat -antup|grep 25 



tcp 0 0 0.0.0.0:25 0.0.0.0:* LISTEN 29478/master




iptables -L|grep smtp 



ACCEPT tcp -- anywhere anywhere tcp
multiport dports smtp,pop3 state NEW




openssl s_client -connect myDomain.com:25 -servername mailserver.com -starttls smtp



CONNECTED(00000003)

depth=2 O = Digital Signature Trust Co., CN = DST Root CA X3

verify return:1

depth=1 C = US, O = Let's Encrypt, CN = Let's Encrypt Authority X3

verify return:1

depth=0 CN = mail.mailServer.com

verify return:1

--- Certificate chain

0 s:/CN=mail.mailServer.com

i:/C=US/O=Let's Encrypt/CN=Let's Encrypt Authority X3

1 s:/C=US/O=Let's Encrypt/CN=Let's Encrypt Authority X3

i:/O=Digital Signature Trust Co./CN=DST Root CA X3



Server certificate

-----BEGIN CERTIFICATE-----

...the output continues with more data




enter image description here



Before enabling SSL mail exchange was good from both servers (protonmail and mine).

My IP is not listed as spam in any of abuse trackers.

Let's Encrypt certificate.

I contacted support of protonmail but they didn't answer.
I worry I would have to face this issue with another particular mailserver like protonmail.



What I ask first is how to look into this is issue, which other logs, settings or command outputs do you recommend to post here to improve the question.










share|improve this question























  • "telnet protonmail.com 25" - the mail servers for protonmail are currently mail.protonmail.ch and mailsec.protonmail.ch. You need to do an MX lookup to get the mailserver first, not just try to connect on port 25 of the mail domain.
    – Steffen Ullrich
    2 days ago











  • If mail to all servers work but not from you to protonmail and back and the connections attempts time out then it might be a firewall or routing issue. Contact the provider where you have the server for help to debug the issue. It has most likely nothing to do with enabling SSL.
    – Steffen Ullrich
    2 days ago











  • @SteffenUllrich But befor installing SSL mail exchange was okay. I changed telnet to one of those mail servers: Connected, connection closed by foreign host
    – dstonek
    2 days ago











  • "But befor installing SSL mail exchange was okay." - I don't know what you exactly did to installing SSL (no description in question) but either you did something which was not needed or there were some unrelated changes at the same time (assuming everything worked before). If you think it is related to SSL try to change everything back and see if this helps. If it does please describe what exactly you did.
    – Steffen Ullrich
    yesterday











  • I essentially followed instructions from linuxbabe.com/mail-server/… (on Apache)
    – dstonek
    yesterday














up vote
0
down vote

favorite












Extending the title:
After enabling SSL encryption I have no problems sending emails from client (Thundirbird) and webmail (Horde and Squirrelmail) to all servers I tried like gmail, hotmail, yahoo and others.

The exception is, at least for now, protonmail.com

Postfix has mail to send them in queue (24 hours +).



Oct 6 20:00:37 host postfix/smtp[15295]: connect to mailsec.protonmail.ch[185.70.40.102]:25: Connection timed out
Oct 6 20:00:37 host postfix/smtp[15295]: A71AA1CA1A17: to=<fff@protonmail.com>, relay=none, delay=6199, delays=6139/0.05/60/0, dsn=4.4.1, status=deferred (connect to mailsec.protonmail.ch[185.70.40.102]:25: Connection timed out)


The issue is also sending mail from protonmail.com to my mail server.

This happens also only with this mail server.

I have a undelivered message source I got from the sender.




Diagnostic-Code: X-Postfix; Host or domain name not found. Name service error for name=myDomain.com type=MX: Host not found, try again




nslookup -type=mx myDomain.com



Server: 127.0.0.53

Address: 127.0.0.53#53

Non-authoritative answer:

myDomain.com mail exchanger = 5 mail.mailServer.com.




telnet mailsec.protonmail.ch 25 



Trying 185.70.40.102...

Connected to mailsec.protonmail.ch

Escape character is '^]'

Connection close by foreign host




 netstat -antup|grep 25 



tcp 0 0 0.0.0.0:25 0.0.0.0:* LISTEN 29478/master




iptables -L|grep smtp 



ACCEPT tcp -- anywhere anywhere tcp
multiport dports smtp,pop3 state NEW




openssl s_client -connect myDomain.com:25 -servername mailserver.com -starttls smtp



CONNECTED(00000003)

depth=2 O = Digital Signature Trust Co., CN = DST Root CA X3

verify return:1

depth=1 C = US, O = Let's Encrypt, CN = Let's Encrypt Authority X3

verify return:1

depth=0 CN = mail.mailServer.com

verify return:1

--- Certificate chain

0 s:/CN=mail.mailServer.com

i:/C=US/O=Let's Encrypt/CN=Let's Encrypt Authority X3

1 s:/C=US/O=Let's Encrypt/CN=Let's Encrypt Authority X3

i:/O=Digital Signature Trust Co./CN=DST Root CA X3



Server certificate

-----BEGIN CERTIFICATE-----

...the output continues with more data




enter image description here



Before enabling SSL mail exchange was good from both servers (protonmail and mine).

My IP is not listed as spam in any of abuse trackers.

Let's Encrypt certificate.

I contacted support of protonmail but they didn't answer.
I worry I would have to face this issue with another particular mailserver like protonmail.



What I ask first is how to look into this is issue, which other logs, settings or command outputs do you recommend to post here to improve the question.










share|improve this question























  • "telnet protonmail.com 25" - the mail servers for protonmail are currently mail.protonmail.ch and mailsec.protonmail.ch. You need to do an MX lookup to get the mailserver first, not just try to connect on port 25 of the mail domain.
    – Steffen Ullrich
    2 days ago











  • If mail to all servers work but not from you to protonmail and back and the connections attempts time out then it might be a firewall or routing issue. Contact the provider where you have the server for help to debug the issue. It has most likely nothing to do with enabling SSL.
    – Steffen Ullrich
    2 days ago











  • @SteffenUllrich But befor installing SSL mail exchange was okay. I changed telnet to one of those mail servers: Connected, connection closed by foreign host
    – dstonek
    2 days ago











  • "But befor installing SSL mail exchange was okay." - I don't know what you exactly did to installing SSL (no description in question) but either you did something which was not needed or there were some unrelated changes at the same time (assuming everything worked before). If you think it is related to SSL try to change everything back and see if this helps. If it does please describe what exactly you did.
    – Steffen Ullrich
    yesterday











  • I essentially followed instructions from linuxbabe.com/mail-server/… (on Apache)
    – dstonek
    yesterday












up vote
0
down vote

favorite









up vote
0
down vote

favorite











Extending the title:
After enabling SSL encryption I have no problems sending emails from client (Thundirbird) and webmail (Horde and Squirrelmail) to all servers I tried like gmail, hotmail, yahoo and others.

The exception is, at least for now, protonmail.com

Postfix has mail to send them in queue (24 hours +).



Oct 6 20:00:37 host postfix/smtp[15295]: connect to mailsec.protonmail.ch[185.70.40.102]:25: Connection timed out
Oct 6 20:00:37 host postfix/smtp[15295]: A71AA1CA1A17: to=<fff@protonmail.com>, relay=none, delay=6199, delays=6139/0.05/60/0, dsn=4.4.1, status=deferred (connect to mailsec.protonmail.ch[185.70.40.102]:25: Connection timed out)


The issue is also sending mail from protonmail.com to my mail server.

This happens also only with this mail server.

I have a undelivered message source I got from the sender.




Diagnostic-Code: X-Postfix; Host or domain name not found. Name service error for name=myDomain.com type=MX: Host not found, try again




nslookup -type=mx myDomain.com



Server: 127.0.0.53

Address: 127.0.0.53#53

Non-authoritative answer:

myDomain.com mail exchanger = 5 mail.mailServer.com.




telnet mailsec.protonmail.ch 25 



Trying 185.70.40.102...

Connected to mailsec.protonmail.ch

Escape character is '^]'

Connection close by foreign host




 netstat -antup|grep 25 



tcp 0 0 0.0.0.0:25 0.0.0.0:* LISTEN 29478/master




iptables -L|grep smtp 



ACCEPT tcp -- anywhere anywhere tcp
multiport dports smtp,pop3 state NEW




openssl s_client -connect myDomain.com:25 -servername mailserver.com -starttls smtp



CONNECTED(00000003)

depth=2 O = Digital Signature Trust Co., CN = DST Root CA X3

verify return:1

depth=1 C = US, O = Let's Encrypt, CN = Let's Encrypt Authority X3

verify return:1

depth=0 CN = mail.mailServer.com

verify return:1

--- Certificate chain

0 s:/CN=mail.mailServer.com

i:/C=US/O=Let's Encrypt/CN=Let's Encrypt Authority X3

1 s:/C=US/O=Let's Encrypt/CN=Let's Encrypt Authority X3

i:/O=Digital Signature Trust Co./CN=DST Root CA X3



Server certificate

-----BEGIN CERTIFICATE-----

...the output continues with more data




enter image description here



Before enabling SSL mail exchange was good from both servers (protonmail and mine).

My IP is not listed as spam in any of abuse trackers.

Let's Encrypt certificate.

I contacted support of protonmail but they didn't answer.
I worry I would have to face this issue with another particular mailserver like protonmail.



What I ask first is how to look into this is issue, which other logs, settings or command outputs do you recommend to post here to improve the question.










share|improve this question















Extending the title:
After enabling SSL encryption I have no problems sending emails from client (Thundirbird) and webmail (Horde and Squirrelmail) to all servers I tried like gmail, hotmail, yahoo and others.

The exception is, at least for now, protonmail.com

Postfix has mail to send them in queue (24 hours +).



Oct 6 20:00:37 host postfix/smtp[15295]: connect to mailsec.protonmail.ch[185.70.40.102]:25: Connection timed out
Oct 6 20:00:37 host postfix/smtp[15295]: A71AA1CA1A17: to=<fff@protonmail.com>, relay=none, delay=6199, delays=6139/0.05/60/0, dsn=4.4.1, status=deferred (connect to mailsec.protonmail.ch[185.70.40.102]:25: Connection timed out)


The issue is also sending mail from protonmail.com to my mail server.

This happens also only with this mail server.

I have a undelivered message source I got from the sender.




Diagnostic-Code: X-Postfix; Host or domain name not found. Name service error for name=myDomain.com type=MX: Host not found, try again




nslookup -type=mx myDomain.com



Server: 127.0.0.53

Address: 127.0.0.53#53

Non-authoritative answer:

myDomain.com mail exchanger = 5 mail.mailServer.com.




telnet mailsec.protonmail.ch 25 



Trying 185.70.40.102...

Connected to mailsec.protonmail.ch

Escape character is '^]'

Connection close by foreign host




 netstat -antup|grep 25 



tcp 0 0 0.0.0.0:25 0.0.0.0:* LISTEN 29478/master




iptables -L|grep smtp 



ACCEPT tcp -- anywhere anywhere tcp
multiport dports smtp,pop3 state NEW




openssl s_client -connect myDomain.com:25 -servername mailserver.com -starttls smtp



CONNECTED(00000003)

depth=2 O = Digital Signature Trust Co., CN = DST Root CA X3

verify return:1

depth=1 C = US, O = Let's Encrypt, CN = Let's Encrypt Authority X3

verify return:1

depth=0 CN = mail.mailServer.com

verify return:1

--- Certificate chain

0 s:/CN=mail.mailServer.com

i:/C=US/O=Let's Encrypt/CN=Let's Encrypt Authority X3

1 s:/C=US/O=Let's Encrypt/CN=Let's Encrypt Authority X3

i:/O=Digital Signature Trust Co./CN=DST Root CA X3



Server certificate

-----BEGIN CERTIFICATE-----

...the output continues with more data




enter image description here



Before enabling SSL mail exchange was good from both servers (protonmail and mine).

My IP is not listed as spam in any of abuse trackers.

Let's Encrypt certificate.

I contacted support of protonmail but they didn't answer.
I worry I would have to face this issue with another particular mailserver like protonmail.



What I ask first is how to look into this is issue, which other logs, settings or command outputs do you recommend to post here to improve the question.







email postfix ssl






share|improve this question















share|improve this question













share|improve this question




share|improve this question








edited 10 hours ago

























asked 2 days ago









dstonek

104117




104117











  • "telnet protonmail.com 25" - the mail servers for protonmail are currently mail.protonmail.ch and mailsec.protonmail.ch. You need to do an MX lookup to get the mailserver first, not just try to connect on port 25 of the mail domain.
    – Steffen Ullrich
    2 days ago











  • If mail to all servers work but not from you to protonmail and back and the connections attempts time out then it might be a firewall or routing issue. Contact the provider where you have the server for help to debug the issue. It has most likely nothing to do with enabling SSL.
    – Steffen Ullrich
    2 days ago











  • @SteffenUllrich But befor installing SSL mail exchange was okay. I changed telnet to one of those mail servers: Connected, connection closed by foreign host
    – dstonek
    2 days ago











  • "But befor installing SSL mail exchange was okay." - I don't know what you exactly did to installing SSL (no description in question) but either you did something which was not needed or there were some unrelated changes at the same time (assuming everything worked before). If you think it is related to SSL try to change everything back and see if this helps. If it does please describe what exactly you did.
    – Steffen Ullrich
    yesterday











  • I essentially followed instructions from linuxbabe.com/mail-server/… (on Apache)
    – dstonek
    yesterday
















  • "telnet protonmail.com 25" - the mail servers for protonmail are currently mail.protonmail.ch and mailsec.protonmail.ch. You need to do an MX lookup to get the mailserver first, not just try to connect on port 25 of the mail domain.
    – Steffen Ullrich
    2 days ago











  • If mail to all servers work but not from you to protonmail and back and the connections attempts time out then it might be a firewall or routing issue. Contact the provider where you have the server for help to debug the issue. It has most likely nothing to do with enabling SSL.
    – Steffen Ullrich
    2 days ago











  • @SteffenUllrich But befor installing SSL mail exchange was okay. I changed telnet to one of those mail servers: Connected, connection closed by foreign host
    – dstonek
    2 days ago











  • "But befor installing SSL mail exchange was okay." - I don't know what you exactly did to installing SSL (no description in question) but either you did something which was not needed or there were some unrelated changes at the same time (assuming everything worked before). If you think it is related to SSL try to change everything back and see if this helps. If it does please describe what exactly you did.
    – Steffen Ullrich
    yesterday











  • I essentially followed instructions from linuxbabe.com/mail-server/… (on Apache)
    – dstonek
    yesterday















"telnet protonmail.com 25" - the mail servers for protonmail are currently mail.protonmail.ch and mailsec.protonmail.ch. You need to do an MX lookup to get the mailserver first, not just try to connect on port 25 of the mail domain.
– Steffen Ullrich
2 days ago





"telnet protonmail.com 25" - the mail servers for protonmail are currently mail.protonmail.ch and mailsec.protonmail.ch. You need to do an MX lookup to get the mailserver first, not just try to connect on port 25 of the mail domain.
– Steffen Ullrich
2 days ago













If mail to all servers work but not from you to protonmail and back and the connections attempts time out then it might be a firewall or routing issue. Contact the provider where you have the server for help to debug the issue. It has most likely nothing to do with enabling SSL.
– Steffen Ullrich
2 days ago





If mail to all servers work but not from you to protonmail and back and the connections attempts time out then it might be a firewall or routing issue. Contact the provider where you have the server for help to debug the issue. It has most likely nothing to do with enabling SSL.
– Steffen Ullrich
2 days ago













@SteffenUllrich But befor installing SSL mail exchange was okay. I changed telnet to one of those mail servers: Connected, connection closed by foreign host
– dstonek
2 days ago





@SteffenUllrich But befor installing SSL mail exchange was okay. I changed telnet to one of those mail servers: Connected, connection closed by foreign host
– dstonek
2 days ago













"But befor installing SSL mail exchange was okay." - I don't know what you exactly did to installing SSL (no description in question) but either you did something which was not needed or there were some unrelated changes at the same time (assuming everything worked before). If you think it is related to SSL try to change everything back and see if this helps. If it does please describe what exactly you did.
– Steffen Ullrich
yesterday





"But befor installing SSL mail exchange was okay." - I don't know what you exactly did to installing SSL (no description in question) but either you did something which was not needed or there were some unrelated changes at the same time (assuming everything worked before). If you think it is related to SSL try to change everything back and see if this helps. If it does please describe what exactly you did.
– Steffen Ullrich
yesterday













I essentially followed instructions from linuxbabe.com/mail-server/… (on Apache)
– dstonek
yesterday




I essentially followed instructions from linuxbabe.com/mail-server/… (on Apache)
– dstonek
yesterday















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