Cannot send mail through desktop clients, can through Webmail, Gmail

Posts: 1
Joined: Sun Nov 05, 2017 8:07 am

Cannot send mail through desktop clients, can through Webmail, Gmail

Postby regjo » Sun Nov 05, 2017 6:09 pm

Important summary: Can receive mail through any client. Can only send mail using gmail as the client, with the server set properly ( I would greatly appreciate ANY help. What was supposed to be an alt-tab, create email account, turned into a multi-hour struggle.

I'm trying to setup my first site on a GoDaddy VPS. The server (Plesk on Windows) is running ESMTP MailEnable Service v9. I can connect to and send/recieve from the webmail interface.

Thunderbird was unable to connect in any fasion. OperaMail is at least able to check mail but was unable to send a message, regardless of outgoing subdomain used (I tried, mail.--, webmail.--, smtp.--).

I have run the gambit of suggested ports both for secure and non-secure.

On a whim, I added the account to m Gmail account and gmail has no trouble receiving/sending. Gmail says it was mailed by my domain (and not gmail), using webmail.-- for sending and recieving..

I downloaded **eM Client** which at least makes an effort to fix error and is good at communicating why it failed.

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    5:23:52 PM [--account--] [SMTP]  MailClient.Accounts.SocketException: Connection failed due to the following reason:
    5:23:52 PM     "A connection attempt failed because the connected party
                    did not properly respond after a period of time, or
                    established connection failed because connected host
                    has failed to respond [ip]:25"
    5:23:52 PM    at MailClient.Protocols.Smtp.SmtpSendCommand.Connect(WorkerStatus status)
    5:23:52 PM    at MailClient.Protocols.Smtp.SmtpSendCommand.Execute(WorkerStatus status)
    5:23:52 PM    at MailClient.Commands.Command.Process(WorkerStatus status)

I can, and am going to, run the gambit of ports with **eM Client** to see if I get a more-helpful error (or, fix the problem).

Here are, of course, the logs generated from Plesk's installation of MailEnable.

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    11/04/17 16:13:47   ME-I0135: Authenticating User:user@S132 using Authentication Provider Credentials
    11/04/17 16:13:47   ME-I0074: [740] (Debug) End of conversation
    2017-11-04 16:13:46 SMTP-IN  [server ip] 740 EHLO EHLO+User 250-home+[],+this+server+offers+4+extensions S132 120 11
    2017-11-04 16:13:46 SMTP-IN  [server ip] 740 RSET RSET 250+Requested+mail+action+okay,+completed S132 43 6 
    2017-11-04 16:13:47 SMTP-IN  [server ip] 740 AUTH AUTH+LOGIN 334+VXNlcm5hbWU6 S132 18 12 
    2017-11-04 16:13:47 SMTP-IN  [server ip] 740 AUTH {blank} 334+UGFzc3dvcmQ6 S132 18 38 user@S132
    2017-11-04 16:13:47 SMTP-IN  [server ip] 740 AUTH bG92ZXI= 504+Invalid+Username+or+Password S132 34 10 user@S132
    2017-11-04 16:13:47 SMTP-IN  [server ip] 740 QUIT QUIT 221+Service+closing+transmission+channel S132 42 6 user@S132
    activity log:
    11/04/17 16:13:46   SMTP-IN   5C9DB3371FE942A09A848D7A08B34068.MAI   740            220 S132 ESMTP MailEnable Service, Version: 9.00-- ready at 11/04/17 16:13:46   0   0   
    11/04/17 16:13:46   SMTP-IN   5C9DB3371FE942A09A848D7A08B34068.MAI   740   EHLO   EHLO User   250-home [], this server offers 4 extensions   120   11   
    11/04/17 16:13:46   SMTP-IN   5C9DB3371FE942A09A848D7A08B34068.MAI   740   RSET   RSET      250 Requested mail action okay, completed   43   6   
    11/04/17 16:13:47   SMTP-IN   5C9DB3371FE942A09A848D7A08B34068.MAI   740   AUTH   AUTH LOGIN   334 VXNlcm5hbWU6   18   12   
    11/04/17 16:13:47   SMTP-IN   5C9DB3371FE942A09A848D7A08B34068.MAI   740   AUTH   {blank}      334 UGFzc3dvcmQ6   18   38   user@S132
    11/04/17 16:13:47   SMTP-IN   5C9DB3371FE942A09A848D7A08B34068.MAI   740   AUTH   bG92ZXI=   504 Invalid Username or Password   34   10   user@S132
    11/04/17 16:13:47   SMTP-IN   5C9DB3371FE942A09A848D7A08B34068.MAI   740   QUIT   QUIT      221 Service closing transmission channel   42   6   user@S132

None of the above mentioned the login that I'm using, which is my email address.

Here is a log of one the successful sends (also able to receive) via gmail with, by all accounts, all the same information entered. for what it's worth, my domain doesn't offer gmailify):

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    2017-11-04 16:22:53 SMTP-IN [server ip] 764 MAIL MAIL+FROM:<>+SIZE=1236 250+Requested+mail+action+okay,+completed S132 43 42
    2017-11-04 16:22:53 SMTP-IN [server ip] 764 RCPT RCPT+TO:<> 250+Requested+mail+action+okay,+completed S132 43 30
    2017-11-04 16:22:53 SMTP-IN [server ip] 764 DATA DATA 354+Start+mail+input;+end+with+<CRLF>.<CRLF> S132 46 6
    2017-11-04 16:22:53 SMTP-IN [server ip] 764 DATA DATA 354+Start+mail+input;+end+with+<CRLF>.<CRLF> S132 43 1239
    2017-11-04 16:22:53 SMTP-IN [server ip] 764 QUIT QUIT 221+Service+closing+transmission+channel S132 42 6
    2017-11-04 16:22:54 SMTP-OU  636 CONN   S132 0 102
    2017-11-04 16:22:54 SMTP-OU  636 EHLO S132 27 167
    2017-11-04 16:22:54 SMTP-OU  636 MAIL EHLO+S132[[server ip]],+pleased+to+meet+you S132 42 42
    2017-11-04 16:22:54 SMTP-OU  636 RCPT MAIL+FROM:<>+SIZE=1356 250+2.1.0+<>+sender+ok S132 30 45
    2017-11-04 16:22:54 SMTP-OU  636 DATA RCPT+TO:<> 250+2.1.5+<>+recipient+ok S132 6 8
    2017-11-04 16:22:54 SMTP-OU  636 DATE DATA 354+OK S132 1365 52
    2017-11-04 16:22:54 SMTP-OU  636 QUIT . 250+2.0.0+B7m6egOSo2fbL+mail+accepted+for+delivery S132 6 90

The fact that **gmail** can send through the server makes clear that the mail server is set up properly, so I'm wondering if anyone else has a tip on why gmail can fully connect to the email address but desktop clients cannot.

I disabled my firewall and had no affect on the process. Desktop clients from other systems cannot connect either.

Lastly, here is a scan from mxtoolbox. The server doesn't have a secure cert yet--which mxtoolbox notes, but Gmail says it's connecting over TLS.

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        SMTP Banner Check   Reverse DNS does not match SMTP Banner    More Info
        // This doesn't matter towards the direct ability to send mail
       SMTP TLS   Warning - Does not support TLS.    More Info
       SMTP Reverse DNS Mismatch   OK - [ip address] resolves to   
       SMTP Valid Hostname   OK - Reverse DNS is a valid Hostname   
       SMTP Connection Time   0.701 seconds - Good on Connection time   
       SMTP Open Relay   OK - Not an open relay.   
       SMTP Transaction Time   2.769 seconds - Good on Transaction Time

Update: "Diagnose" in WebEnable gave me this

  • Image

Doing this gives me success there and two new boxes with their own warnings/failures but the second box in this image seems unrelated.

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Re: Cannot send mail through desktop clients, can through Webmail, Gmail

Postby MailEnable-Ian » Tue Nov 07, 2017 11:00 pm


The failures in the MailEnable diagnostic report indicate that the DNS Addresses that you have specified for DNS resolution within the MailEnable SMTP properties are not able to resolve external domains. Ensure that the DNS address is an IP address and that the IP address of the DNS server is one that is used by the servers NIC. Please see:

I can see that you are also running version 9.00 of MailEnable standard edition. You really need to download 9.78 and upgrade as it contains extensive fixes to MailEnable core services you need to apply. Here is an article that explains how to upgrade MailEnable on a Plesk platform:

Once you have upgraded and fixed the DNS resolution problems in MailEnable try your tests again and report back.

Ian Margarone
MailEnable Support

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