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

[regjo]

Important summary: Can receive mail through any client. Can only send mail using gmail as the client, with the server set properly (webmail.mydomain.com) 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 domain.com, 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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    debug.log
    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
    
    ex171110416.log
    2017-11-04 16:13:46 191.96.249.70 SMTP-IN  [server ip] 740 EHLO EHLO+User 250-home+[191.96.249.70],+this+server+offers+4+extensions S132 120 11 
    2017-11-04 16:13:46 191.96.249.70 SMTP-IN  [server ip] 740 RSET RSET 250+Requested+mail+action+okay,+completed S132 43 6  
    2017-11-04 16:13:47 191.96.249.70 SMTP-IN  [server ip] 740 AUTH AUTH+LOGIN 334+VXNlcm5hbWU6 S132 18 12  
    2017-11-04 16:13:47 191.96.249.70 SMTP-IN  [server ip] 740 AUTH {blank} 334+UGFzc3dvcmQ6 S132 18 38 user@S132
    2017-11-04 16:13:47 191.96.249.70 SMTP-IN  [server ip] 740 AUTH bG92ZXI= 504+Invalid+Username+or+Password S132 34 10 user@S132
    2017-11-04 16:13:47 191.96.249.70 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	191.96.249.70				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	191.96.249.70	EHLO	EHLO User	250-home [191.96.249.70], this server offers 4 extensions	120	11	
    11/04/17 16:13:46	SMTP-IN	5C9DB3371FE942A09A848D7A08B34068.MAI	740	191.96.249.70	RSET	RSET		250 Requested mail action okay, completed	43	6	
    11/04/17 16:13:47	SMTP-IN	5C9DB3371FE942A09A848D7A08B34068.MAI	740	191.96.249.70	AUTH	AUTH LOGIN	334 VXNlcm5hbWU6	18	12	
    11/04/17 16:13:47	SMTP-IN	5C9DB3371FE942A09A848D7A08B34068.MAI	740	191.96.249.70	AUTH	{blank}		334 UGFzc3dvcmQ6	18	38	user@S132
    11/04/17 16:13:47	SMTP-IN	5C9DB3371FE942A09A848D7A08B34068.MAI	740	191.96.249.70	AUTH	bG92ZXI=	504 Invalid Username or Password	34	10	user@S132
    11/04/17 16:13:47	SMTP-IN	5C9DB3371FE942A09A848D7A08B34068.MAI	740	191.96.249.70	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 16:22:53 209.85.214.47 SMTP-IN domain.com [server ip] 764 MAIL MAIL+FROM:<user@domain.com>+SIZE=1236 250+Requested+mail+action+okay,+completed S132 43 42 user@domain.com 
    2017-11-04 16:22:53 209.85.214.47 SMTP-IN domain.com [server ip] 764 RCPT RCPT+TO:<my_gmail@gmail.com> 250+Requested+mail+action+okay,+completed S132 43 30 user@domain.com 
    2017-11-04 16:22:53 209.85.214.47 SMTP-IN domain.com [server ip] 764 DATA DATA 354+Start+mail+input;+end+with+<CRLF>.<CRLF> S132 46 6 user@domain.com 
    2017-11-04 16:22:53 209.85.214.47 SMTP-IN domain.com [server ip] 764 DATA DATA 354+Start+mail+input;+end+with+<CRLF>.<CRLF> S132 43 1239 user@domain.com 
    2017-11-04 16:22:53 209.85.214.47 SMTP-IN domain.com [server ip] 764 QUIT QUIT 221+Service+closing+transmission+channel S132 42 6 user@domain.com 
    2017-11-04 16:22:54 208.109.80.54 SMTP-OU domain.com  636 CONN   S132 0 102 user@domain.com 
    2017-11-04 16:22:54 208.109.80.54 SMTP-OU domain.com  636 EHLO  220+p3plsmtpout001.prod.phx3.secureserver.net+:+HOSTING+RELAY+:+ESMTP+Ded+Hosting+relay+server+ready S132 27 167 user@domain.com 
    2017-11-04 16:22:54 208.109.80.54 SMTP-OU domain.com  636 MAIL EHLO+S132 250-p3plsmtpout001.prod.phx3.secureserver.net+hello+[[server ip]],+pleased+to+meet+you S132 42 42 user@domain.com 
    2017-11-04 16:22:54 208.109.80.54 SMTP-OU domain.com  636 RCPT MAIL+FROM:<user@domain.com>+SIZE=1356 250+2.1.0+<user@domain.com>+sender+ok S132 30 45 user@domain.com 
    2017-11-04 16:22:54 208.109.80.54 SMTP-OU domain.com  636 DATA RCPT+TO:<my_gmail@gmail.com> 250+2.1.5+<my_gmail@gmail.com>+recipient+ok S132 6 8 user@domain.com 
    2017-11-04 16:22:54 208.109.80.54 SMTP-OU domain.com  636 DATE DATA 354+OK S132 1365 52 user@domain.com 
    2017-11-04 16:22:54 208.109.80.54 SMTP-OU domain.com  636 QUIT . 250+2.0.0+B7m6egOSo2fbL+mail+accepted+for+delivery S132 6 90 user@domain.com 

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 --.ip.secureserver.net	
    	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

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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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[MailEnable-Ian]

Hi,

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: http://www.mailenable.com/kb/content/ar ... D=ME020043

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: http://www.mailenable.com/kb/content/ar ... D=me020513

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