Failed to send emails to gmail

[amos]

Hi

After not being able to send emails to any email address, my sysadmin took care of the exim files as explained. Now everything is working except for Gmail. When sending an email to Gmail I either get:
1. all hosts for 'gmail.com' have been failing for a long time (and retry time not reached)
2. host alt4.gmail-smtp-in.l.google.com [74.125.193.26] retry timeout exceeded

When doing exim -bt .... I get
router = dnslookup, transport = remote_smtp
host gmail-smtp-in.l.google.com [74.125.197.26] MX=5
host alt1.gmail-smtp-in.l.google.com [209.85.200.27] MX=10
host alt2.gmail-smtp-in.l.google.com [74.125.21.27] MX=20
host alt3.gmail-smtp-in.l.google.com [209.85.144.27] MX=30
host alt4.gmail-smtp-in.l.google.com [74.125.141.27] MX=40

All other addresses working perfectly, what else can be done?
I'm using 4.91 (on ubuntu). My sysadmin said that 4.92 is still not available.
Thanks

Edit: I get the following when emailing using exim itself:

gmail-smtp-in.l.google.com [74.125.197.27] TLS error on connection (recv): Resource temporarily unavailable, try again.
gmail-smtp-in.l.google.com [74.125.197.27]: Remote host closed connection in response to EHLO mail...
alt1.gmail-smtp-in.l.google.com [209.85.200.27] TLS error on connection (recv): Resource temporarily unavailable, try again.
alt1.gmail-smtp-in.l.google.com [209.85.200.27]: alt1.gmail-smtp-in.l.google.com [209.85.200.27]: No such file or directory
[email protected] R=dnslookup T=remote_smtp defer (2): No such file or directory H=alt1.gmail-smtp-in.l.google.com [209.85.200.27]: [email protected]: retry timeout exceeded

[HenrysCat]

Have you tried sending an email to https://www.mail-tester.com/ it can tell you a lot.

[amos]

Did already, 10/10 :)

[HenrysCat]

What about this one? https://www.checktls.com/TestReceiver

[amos]

I get this
Certificate 1 of 1 in chain: Cert VALIDATION ERROR(S): unable to get local issuer certificate; unable to verify the first certificate
This may help: What Is An Intermediate Certificate
So email is encrypted but the recipient domain is not verified

Which might be related but I have no idea what to do with it. All other tests in this page are ok...

[HenrysCat]

Do you have an SSL cert on the server? if so it must contain both the domain and the mail domain, e.g. mydomian.com & mail.mydomain.com

[amos]

I'm on my way there, I use this site viewtopic.php?t=17151
but I'm stuck in this step "Now go to your EXIM.conf, probably located in /etc/exim/exim.conf and search for: tls_privatekey, then comment:"

I didn't find exim folder,I did see exim4 under etc but there is no exim.conf file there. I've found update-exim4.conf.conf but it doesn't seem to have what the guide says. I'm a bit lost here.

[HenrysCat]

This is the thread you want viewtopic.php?f=19&t=12617&p=72195#p72195

[amos]

Thanks, apparently there was a configuration problem with my VPS that my sysadmin fixed and managed the required changes

[amos]

Unfortunately it doesn't seem to help: https://www.checktls.com/TestReceiver now shows OK for everything but I did the following using ssh:

$ exim -v [email protected]
from: [email protected]
subject: testing gmail
this is a test, did you receive it?
LOG: MAIN
<= [email protected] U=... P=local S=362
...@mail:~$ delivering 1hldYm-000Wx3-A7
LOG: retry_defer MAIN
== [email protected] R=dnslookup T=remote_smtp defer (-53): retry time not reached for any host for 'gmail.com'