Outlook not able to connect to zimbra

[michael24]

Is this the correct IP address? When I do a port scan on that IP address, I don't see any ports open for mail services. I see the following:

PORT STATE SERVICE VERSION
135/tcp filtered msrpc
139/tcp filtered netbios-ssn
445/tcp filtered microsoft-ds
593/tcp filtered http-rpc-epmap
64623/tcp filtered unknown
64680/tcp filtered unknown

I should see all of the open ports you noted above for mail services (25, 143, etc). This would explain the timeouts and such. Make sure your external firewall is set up to forward requests to the appropriate internal IP address.

You can test this yourself by typing the following at your *nix command line from an external computer (which is what any mail clients would see): nmap -A -T4 75.141.200.126

When I do a telnet to the pop.hilltopchurchnet.net 110 I get +OK mail.hilltopchurchnet.net Zimbra POP3 server Ready

And imap.hilltopchurchnet.net 143 get +OK mail.hilltopchurchnet.net Zimbra POP3 server Ready

so I can get to the server though telnet and nmap does not work with windows computers fyi.

[jfx81]

You know, looking back at your post number 7; Zimbra is very finicky about DNS information as well has local host information... Check out this post and see if any of their suggestions help:
[SOLVED] ERROR LOG: Name or service not known

[michael24]

When I did cat /etc/resolv.conf I got the following

cat /etc/resolv.conf
search hcc.hilltopchurchnet.net
nameserver 192.168.30.3
nameserver 192.168.128.230
nameserver 192.168.128.235

the hcc.hilltopchurchnet.net is the domain controller internally

I tired this as well

cat /etc/resolv.conf
search hilltopchurchnet.net
nameserver 192.168.30.3
nameserver 192.168.128.230
nameserver 192.168.128.235

Still getting

Log onto incoming mail server (POP3): Outlook cannot connect to your incoming (POP3) e-mail server. If you continue to receive this message, contact your server administrator or Internet service provider (ISP).

Send test e-mail message: Outlook cannot connect to your outgoing (SMTP) e-mail server. If you continue to receive this message, contact your server administrator or Internet service provider (ISP).

In outlook.

Below is a trace ran on the internal network and you can see the traffic going to zimbra.

[michael24]

When I try to setup pop3 like I said outlook keeps asking for the username and password so it is like zimbra is not answering the request.

[jfx81]

Will you post the output of the following?

tail -n 30 /var/log/zimbra.log
cat /etc/hosts
host `hostname`

Will you also send me a pm with an email address on the Zimbra server so I can send it a message and review the error message?

[michael24]

Will you post the output of the following?

tail -n 30 /var/log/zimbra.log
cat /etc/hosts
host `hostname`

Will you also send me a pm with an email address on the Zimbra server so I can send it a message and review the error message?

tail -n 30 /var/log/zimbra.log
Jun 4 17:15:48 hilltopchurchnet zmmailboxdmgr[9198]: status requested
Jun 4 17:15:48 hilltopchurchnet zmmailboxdmgr[9198]: status OK
Jun 4 17:16:06 hilltopchurchnet zmmailboxdmgr[9557]: status requested
Jun 4 17:16:06 hilltopchurchnet zmmailboxdmgr[9557]: status OK
Jun 4 17:16:51 hilltopchurchnet zmmailboxdmgr[9749]: status requested
Jun 4 17:16:51 hilltopchurchnet zmmailboxdmgr[9749]: status OK
Jun 4 17:16:51 hilltopchurchnet zmmailboxdmgr[9757]: status requested
Jun 4 17:16:51 hilltopchurchnet zmmailboxdmgr[9757]: status OK
Jun 4 17:17:54 hilltopchurchnet zmmailboxdmgr[9976]: status requested
Jun 4 17:17:54 hilltopchurchnet zmmailboxdmgr[9976]: status OK
Jun 4 17:17:54 hilltopchurchnet zmmailboxdmgr[9984]: status requested
Jun 4 17:17:54 hilltopchurchnet zmmailboxdmgr[9984]: status OK
Jun 4 17:18:06 hilltopchurchnet zmmailboxdmgr[10343]: status requested
Jun 4 17:18:06 hilltopchurchnet zmmailboxdmgr[10343]: status OK
Jun 4 17:18:57 hilltopchurchnet zmmailboxdmgr[10535]: status requested
Jun 4 17:18:57 hilltopchurchnet zmmailboxdmgr[10535]: status OK
Jun 4 17:18:57 hilltopchurchnet zmmailboxdmgr[10543]: status requested
Jun 4 17:18:57 hilltopchurchnet zmmailboxdmgr[10543]: status OK
Jun 4 17:19:46 hilltopchurchnet clamd[19221]: SelfCheck: Database status OK.
Jun 4 17:20:00 hilltopchurchnet zmmailboxdmgr[10761]: status requested
Jun 4 17:20:00 hilltopchurchnet zmmailboxdmgr[10761]: status OK
Jun 4 17:20:00 hilltopchurchnet zmmailboxdmgr[10770]: status requested
Jun 4 17:20:00 hilltopchurchnet zmmailboxdmgr[10770]: status OK
Jun 4 17:20:01 hilltopchurchnet zimbramon[10828]: 10828:info: 2012-06-04 17:20:01, QUEUE: 0 0
Jun 4 17:20:12 hilltopchurchnet zmmailboxdmgr[11271]: status requested
Jun 4 17:20:12 hilltopchurchnet zmmailboxdmgr[11271]: status OK
Jun 4 17:21:05 hilltopchurchnet zmmailboxdmgr[11471]: status requested
Jun 4 17:21:05 hilltopchurchnet zmmailboxdmgr[11471]: status OK
Jun 4 17:21:05 hilltopchurchnet zmmailboxdmgr[11479]: status requested
Jun 4 17:21:05 hilltopchurchnet zmmailboxdmgr[11479]: status OK

cat /etc/hosts
127.0.0.1 localhost.localdomain localhost
192.168.30.3 hilltopchurchnet.net mail
192.168.30.3 mail.hilltopchurchnet.net mail

# The following lines are desirable for IPv6 capable hosts
::1 localhost ip6-localhost ip6-loopback
fe00::0 ip6-localnet
ff00::0 ip6-mcastprefix
ff02::1 ip6-allnodes
ff02::2 ip6-allrouters

host `hostname`
Host mail not found: 3(NXDOMAIN)

PM sent

[jfx81]

cat /etc/hosts
127.0.0.1 localhost.localdomain localhost
192.168.30.3 hilltopchurchnet.net mail
192.168.30.3 mail.hilltopchurchnet.net mail

Remove the line:
192.168.30.3 hilltopchurchnet.net mail

host `hostname`
Host mail not found: 3(NXDOMAIN)

Failed because it is unable to complete a DNS query correctly. Is your Zimbra server running the "named" service?

Run this command from your Zimbra server's command line:
sudo service named status

If it says "stopped" or "unrecognized" then you should remove the line "nameserver 192.168.30.3" from your resolv.conf file assuming that's the IP of your Zimbra server - which is not a functioning DNS server.

Your /etc/resolv.conf:

search hilltopchurchnet.net
nameserver 192.168.30.3
nameserver 192.168.128.230
nameserver 192.168.128.235

Each of the other nameservers should resolve your Zimbra server's FQDN (mail.hilltopchurchnet.net) if queried - you can verify this by running this on your Windows box:
c:/>nslookup
>server 192.168.30.3
>mail.hilltopchurchnet.net
>192.168.30.3

Repeat those nslookups for each DNS server; replacing the IP after "server" with that of each DNS server to confirm they are working correctly.

If not, make those corrections on the DNS servers and try it again.

[michael24]

Remove the line:
192.168.30.3 hilltopchurchnet.net mail

Done

Failed because it is unable to complete a DNS query correctly. Is your Zimbra server running the "named" service?

Run this command from your Zimbra server's command line:
sudo service named status

If it says "stopped" or "unrecognized" then you should remove the line "nameserver 192.168.30.3" from your resolv.conf file assuming that's the IP of your Zimbra server - which is not a functioning DNS server.

Your /etc/resolv.conf:

Done yes named is not running I have bind running though webmin and the dns server are two Microsoft Windows 2008 domain controllers that are internal.

Each of the other nameservers should resolve your Zimbra server's FQDN (mail.hilltopchurchnet.net) if queried - you can verify this by running this on your Windows box:
c:/>nslookup
>server 192.168.30.3
>mail.hilltopchurchnet.net
>192.168.30.3

Repeat those nslookups for each DNS server; replacing the IP after "server" with that of each DNS server to confirm they are working correctly.

If not, make those corrections on the DNS servers and try it again.

This is what I get

Microsoft Windows [Version 6.0.6002]
Copyright (c) 2006 Microsoft Corporation. All rights reserved.

C:\Users\mturcich>nslookup
Default Server: google-public-dns-a.google.com
Address: 8.8.8.8

> server 192.168.30.3
Default Server: [192.168.30.3]
Address: 192.168.30.3

> mail.hilltopchurchnet.net
Server: [192.168.30.3]
Address: 192.168.30.3

*** [192.168.30.3] can't find mail.hilltopchurchnet.net: Server failed
> 192.168.30.3
Server: [192.168.30.3]
Address: 192.168.30.3

Name: hilltopchurchnet.net
Address: 192.168.30.3

> server 192.168.128.230
Default Server: [192.168.128.230]
Address: 192.168.128.230

> server 192.168.128.235
DNS request timed out.
timeout was 2 seconds.
Default Server: [192.168.128.235]
Address: 192.168.128.235

>

I was able to sent you and email out of the account and was able to send myself one and reply back to it but I can't connect via imap or pop still.

[michael24]

So in trying to figure this out I have gotten the following message tonight from outlook


Send test e-mail message: Your server does not support the connection encryption type you have specified. Try changing the encryption method. Contact your mail server administrator or Internet service provider (ISP) for additional assistance.


That is with outlook set to outgoing smtp port 465 and ssl

I am able to connect to the server via imap.

The network admin is able to connect to smtp when he sets his encryption to auto he is running outlook 2010 vs me running outlook 2007.

I have tired just port 25 no encryption port 587 with ssl and tls

We are able to log directly in with clear text log turned on.

Right now I have TLS turned off on the server but I have SSL turned on for imap and pop.

Anyone have an idea.