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]

7 Replies

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Pedro Soares Replied

12/13/2017 at 6:05 PM

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

12/13/2017 at 6:56 PM

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

12/18/2017 at 4:56 AM

any update on this?

Tim Uzzanti Replied

12/18/2017 at 6:46 AM

Employee Post

Was released on Friday.

Tim Uzzanti CEO SmarterTools Inc. www.smartertools.com

Pedro Soares Replied

12/19/2017 at 4:36 AM

Nop, it's the same. I just updated to the latest versions and still the same.

Matt Petty Replied

12/19/2017 at 9:05 AM

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

3/20/2018 at 5:08 AM

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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