Email Alias stopped sending emails to external email addresses
Problem reported by Pedro Soares - 12/13/2017 at 11:09 AM
Resolved
I got an email from one customer saying thar the email alias stopped delivering emails to external email addresses.
I tested and he is right, created a test alias with internal and external email addresses, sent an email to that alias and I got the email in the local account but not on the external addresses.
for external domain addresses its not sending the FROM:
[2017.12.13] 17:47:13 [63460] CMD: MAIL FROM:< > SIZE=2610
[2017.12.13] 17:47:13 [63460] RSP: 550 5.1.7 Sender address does not conform to RFC-2821 syntax
 
 
Reviewed the log and this is what shows:
 
2017.12.13] 17:47:02 [63460] Delivery started for xxxxx@gmail.com at 17:47:02
[2017.12.13] 17:47:08 [63460] Spam check results: [_REVERSEDNSLOOKUP: passed], [_BAYESIANFILTERING: passed], [_INTERNALSPAMASSASSIN: 0:0], [_SPF: Fail], [_DK: None], [_DKIM: Pass], [BARRACUDA - BRBL: passed], [CBL ABUSE SEAT - NEVER USE TO CHECK OUTGOING E-MAIL: passed], [FIVE-TEN: passed], [HOSTKARMA - BLACKLIST: passed], [HOSTKARMA - BROWNLIST: passed], [HOSTKARMA - WHITELIST: passed], [RBL:  RFC2 REALTIME LIST results passed], [SORBS - ABUSE: passed], [SORBS - DYNAMIC IP: passed], [SORBS - PROXY: passed], [SORBS - SOCKS: passed], [SPAMCOP: passed], [SPAMHAUS - PBL: passed], [SPAMHAUS - PBL2: passed], [SPAMHAUS - SBL: passed], [SPAMHAUS - XBL: passed], [SPAMHAUS - XBL2: passed], [SURBL: passed], [UCEPROTECT LEVEL 1: passed], [UCEPROTECT LEVEL 2: passed], [UCEPROTECT LEVEL 3: passed], [URIBL: passed], [VIRUS RBL - MSRBL: passed]
[2017.12.13] 17:47:11 [63460] Starting local delivery to xxxx@ambifaro.pt
[2017.12.13] 17:47:11 [63460] Delivery for   to xxxxx@ambifaro.pt has completed (Delivered) Filter: None
[2017.12.13] 17:47:11 [63460] End delivery to xxxxx@ambifaro.pt
[2017.12.13] 17:47:11 [63460] Sending remote mail for  
[2017.12.13] 17:47:11 [63460] Initiating connection to 173.194.222.27
[2017.12.13] 17:47:11 [63460] Connecting to 173.194.222.27:25 (Id: 1)
[2017.12.13] 17:47:11 [63460] Binding to local IP 172.25.40.101:0 (Id: 1)
[2017.12.13] 17:47:11 [63460] Connection to 173.194.222.27:25 from 172.25.40.101:60267 succeeded (Id: 1)
[2017.12.13] 17:47:11 [63460] RSP: 220 mx.google.com ESMTP e84si794570lfi.354 - gsmtp
[2017.12.13] 17:47:11 [63460] CMD: EHLO xxxxxhost.xxxl.com
[2017.12.13] 17:47:11 [63460] RSP: 250-mx.google.com at your service, [xxx.xxx.xxx.xxx]
[2017.12.13] 17:47:11 [63460] RSP: 250-SIZE 157286400
[2017.12.13] 17:47:11 [63460] RSP: 250-8BITMIME
[2017.12.13] 17:47:11 [63460] RSP: 250-STARTTLS
[2017.12.13] 17:47:11 [63460] RSP: 250-ENHANCEDSTATUSCODES
[2017.12.13] 17:47:11 [63460] RSP: 250-PIPELINING
[2017.12.13] 17:47:11 [63460] RSP: 250-CHUNKING
[2017.12.13] 17:47:11 [63460] RSP: 250 SMTPUTF8
[2017.12.13] 17:47:11 [63460] CMD: STARTTLS
[2017.12.13] 17:47:11 [63460] RSP: 220 2.0.0 Ready to start TLS
[2017.12.13] 17:47:11 [63460] CMD: EHLO xxxxxhost.xxxl.com
[2017.12.13] 17:47:11 [63460] RSP: 250-mx.google.com at your service, [xxx.xxx.xxx.xxx]
[2017.12.13] 17:47:11 [63460] RSP: 250-SIZE 157286400
[2017.12.13] 17:47:11 [63460] RSP: 250-8BITMIME
[2017.12.13] 17:47:11 [63460] RSP: 250-ENHANCEDSTATUSCODES
[2017.12.13] 17:47:11 [63460] RSP: 250-PIPELINING
[2017.12.13] 17:47:11 [63460] RSP: 250-CHUNKING
[2017.12.13] 17:47:11 [63460] RSP: 250 SMTPUTF8
[2017.12.13] 17:47:11 [63460] CMD: MAIL FROM:< > SIZE=2610
[2017.12.13] 17:47:12 [63460] RSP: 553 5.1.2 The sender address < > is not a valid RFC-5321 address. e84si794570lfi.354 - gsmtp
[2017.12.13] 17:47:12 [63460] CMD: QUIT
[2017.12.13] 17:47:12 [63460] RSP: 221 2.0.0 closing connection e84si794570lfi.354 - gsmtp
[2017.12.13] 17:47:12 [63460] Initiating connection to 54.194.179.173
[2017.12.13] 17:47:12 [63460] Connecting to 54.194.179.173:25 (Id: 2)
[2017.12.13] 17:47:12 [63460] Binding to local IP 172.25.40.101:0 (Id: 2)
[2017.12.13] 17:47:12 [63460] Connection to 54.194.179.173:25 from 172.25.40.101:60268 succeeded (Id: 2)
[2017.12.13] 17:47:12 [63460] RSP: 220 ESMTP
[2017.12.13] 17:47:12 [63460] CMD: EHLO xxxxxhost.xxxl.com
[2017.12.13] 17:47:12 [63460] RSP: 250-mxf.eu.mpssec.net
[2017.12.13] 17:47:12 [63460] RSP: 250-PIPELINING
[2017.12.13] 17:47:12 [63460] RSP: 250-SIZE 52428800
[2017.12.13] 17:47:12 [63460] RSP: 250-ETRN
[2017.12.13] 17:47:12 [63460] RSP: 250-STARTTLS
[2017.12.13] 17:47:12 [63460] RSP: 250-ENHANCEDSTATUSCODES
[2017.12.13] 17:47:12 [63460] RSP: 250-8BITMIME
[2017.12.13] 17:47:12 [63460] RSP: 250 SMTPUTF8
[2017.12.13] 17:47:12 [63460] CMD: STARTTLS
[2017.12.13] 17:47:12 [63460] RSP: 220 2.0.0 Ready to start TLS
[2017.12.13] 17:47:12 [63460] CMD: EHLO xxxxxhost.xxxl.com
[2017.12.13] 17:47:13 [63460] RSP: 250-mxf.eu.mpssec.net
[2017.12.13] 17:47:13 [63460] RSP: 250-PIPELINING
[2017.12.13] 17:47:13 [63460] RSP: 250-SIZE 52428800
[2017.12.13] 17:47:13 [63460] RSP: 250-ETRN
[2017.12.13] 17:47:13 [63460] RSP: 250-ENHANCEDSTATUSCODES
[2017.12.13] 17:47:13 [63460] RSP: 250-8BITMIME
[2017.12.13] 17:47:13 [63460] RSP: 250 SMTPUTF8
[2017.12.13] 17:47:13 [63460] CMD: MAIL FROM:< > SIZE=2610
[2017.12.13] 17:47:13 [63460] RSP: 550 5.1.7 Sender address does not conform to RFC-2821 syntax
[2017.12.13] 17:47:13 [63460] CMD: QUIT
[2017.12.13] 17:47:13 [63460] RSP: 221 2.0.0 Bye
[2017.12.13] 17:47:13 [63460] Delivery for   to xxxxx@gmail.com has completed (Bounced)
[2017.12.13] 17:47:13 [63460] Delivery for   to xxxx@xxxxrma.pt has completed (Bounced)
[2017.12.13] 17:47:14 [63460] Removing Spool message: Killed: False, Failed: False, Finished: True
[2017.12.13] 17:47:14 [63460] Delivery finished for   at 17:47:14 [id:107863460]
Pedro Soares Replied
After some tests, I found a workaround:
Rename Alias and create a new account with the Alias name, after this, redirect all emails received to the new Alias.
Example: old Alias= test@test.com new alias= test2@test.com
create new account= test@test.com --> forward all email to new Alias = test2@test.com

This is only a workaround, But I need this fixedm I have my customers complaining.
Tim Uzzanti Replied
Employee Post
We have a couple support tickets on this and have custom builds out to those customers to see if we fixed the issue.  
Tim Uzzanti CEO SmarterTools Inc. www.smartertools.com
Pedro Soares Replied
any update on this?
Tim Uzzanti Replied
Employee Post
Was released on Friday.
Tim Uzzanti CEO SmarterTools Inc. www.smartertools.com
Pedro Soares Replied
Nop, it's the same. I just updated to the latest versions and still the same.
Matt Petty Replied
Employee Post
Any new deliveries to an alias that delivers externally should work. I just tested it on our live server. You might be seeing a delivery re-attempt from before the update, a case that unfortunately would already be in a broken state. I would make sure you are on atleast 16.3.6558 and then test a new delivery to the alias and confirm it's behavior.
Matt Petty Senior Software Developer SmarterTools Inc. www.smartertools.com
Matthew Sine Replied
As of 03/20/2018
We see this problem still happening on the latest 3/10/2018 build.
 
I replaced alias/email with xxxxxxxxx - but the bounce message is occuring on every attempt to send via an alias due to the receiving email servers stating this is not a valid RFC-5321 Address:
 
*******************************
Bounce
*******************************
Could not deliver message to the following recipient(s):
Failed Recipient: xxxxxxxxxxxxxxxxxxxxxxxx@gmail.com
Reason: Remote host said: 553 5.1.2 The sender address <xxxxxxxxxxxxxxx> is not a valid RFC-5321 address. x47si1874396qta.143 - gsmtp
Failed Recipient: xxxxxxxxxxxxxxxxxxxxxxxxxx@hotmail.com
Reason: Remote host said: 501 5.1.7 Invalid address [SN1NAM02FT002.eop-nam02.prod.protection.outlook.com]

-- The header and top 20 lines of the message follows --
From: "xxxxxxxxxxxx" <alias removed>
To: "xxxxxxxxxxxxxxxxxxxx@gmail.com" <xxxxxxxxxxxxxxxxxxx@gmail.com>, <xxxxxxxxxxxxxxxx@hotmail.com>
Cc:
Bcc:
Date: Tue, 20 Mar 2018 11:54:26 GMT
Subject: TEST Email
Gopost TEst send alias <aliasaddress>
 
Matthew J. Sine, General Manager8Dweb LLC "Making the Web a Happy Place"

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