16.3.6535 - 550 From Address Must Match Authenticated Address

Problem reported by Alex Hee - 11/22/2017 at 11:08 PM

Resolved

After upgraded to 16.3.6535, I received this error message email in my outlook 2013. Funny is the email is sent out & received by recipient. Before this version, I'm using 16.3.6522 without any issue.

Now, in order to fix this issue & I have to go to Settings>Protocols>SMTP In section to change "Require Auth Match" from "Email Address" to "None".

Therefore, what could be the problem? Is it a bug or else?

TQVM.

74 Replies

Reply to Thread

Pedro Soares Replied

11/24/2017 at 2:50 AM

Same here.

Had hundreds of customers calling about this.

Erik Aaskoven Replied

11/24/2017 at 4:43 AM

Have same problem, customers are calling with this problem.

Found that setting "Require Auth Match" to none solve the problem for customers, but not a very good idea.

Mark Lee Replied

11/24/2017 at 12:37 PM

Same here get that message in Outlook... and failed error on cell phones... mail does get sent though...

Gonna go back to previous version of SM I think....

Regards,

Mark L. Lee

Patrick Mattson Replied

11/24/2017 at 8:56 PM

I have been dealing with little things since upgrading. Overview: I went from 14 to 16.

I have noticed and maybe this is coincidence. If I impersonate the account and the account admin is bob@example.com and send a message as bob@example.com it seems to fail with a similar message. Another couple things I noticed is the host name was not associated with the IP anymore and the domain needs a host name.

I added the DNS host name to each spot:

Under the domain, there is a spot below enable/disable the domain a host name is required.

Settings->Bindings (each IP)

A tech replied to my ticket and suggested going back to 15. So over a weekend I would go from 14 to 16 and back to 15. Not the greatest solution, but I may have to take it.

Before I do this I am hoping someone else has a solution.

For those having issues are the people with the issues a domain administrator?

Alaa Majzoub Replied

11/25/2017 at 9:53 AM

Same issue here, many clients facing the issue.

Can anybody help get the software for Version 16.3.6530

I can not find it on Smartermail downloads, they have only the latest one.

This would help a lot to get back to the older version or any version that is tested and stable.

Thanks

James Wilding Replied

11/27/2017 at 1:22 AM

same issue here! hundred of automated system all failing to process correctly as 550 error. Of course all the emails are getting sent out over and over again!

UPDATE PLEASE!

Ionel Aurelian Rau Replied

11/27/2017 at 5:43 AM

Same issue here too!

Tejas Acharya Replied

11/27/2017 at 7:29 AM

Issue is same here too.

Also, i found plenty of messages in spool having status "receiving" only..

but they all are delivered i guess.

is smartertools support is working on this or not !!??

Ionel Aurelian Rau Replied

11/27/2017 at 7:45 AM

Yes, we`ve been trying to find out what`s going on with some mails too.. Many get stuck in the spools with the "Receiving status" and never get delivered. Apparently the larger they are, the more likely to get stuck.

We`ve noticed that if we move just the .eml file (without the corresponding .hdr), then the mail might get delivered.

Also, after watching the logs intensively, these things come up:

[2017.11.27] 16:32:28 [IP][8846677] rsp: 220 ServerName | Mon, 27 Nov 2017 16:32:28 +02:00 GMT | Mon, 27 Nov 2017 14:32:28 +0000 UTC | Attention IP - Sending unsolicited commercial or bulk e-mail to this computer network is prohibited
[2017.11.27] 16:32:28 [IP][8846677] connected at 11/27/2017 4:32:28 PM
[2017.11.27] 16:32:28 [IP][8846677] cmd: EHLO SendingServer
[2017.11.27] 16:32:28 [IP][8846677] rsp: 250-ServerName Hello [IP]250-SIZE 47185920250-AUTH LOGIN CRAM-MD5250-STARTTLS250-8BITMIME250 OK
[2017.11.27] 16:32:28 [IP][8846677] cmd: STARTTLS
[2017.11.27] 16:32:28 [IP][8846677] rsp: 220 Start TLS negotiation
[2017.11.27] 16:32:28 [IP][8846677] cmd: EHLO SendingServer
[2017.11.27] 16:32:28 [IP][8846677] rsp: 250-ServerName Hello [IP]250-SIZE 47185920250-AUTH LOGIN CRAM-MD5250-8BITMIME250 OK
[2017.11.27] 16:32:28 [IP][8846677] cmd: MAIL FROM:<Sender> SIZE=21565874 AUTH=<>
[2017.11.27] 16:32:28 [IP][8846677] rsp: 250 OK <Sender> Sender ok
[2017.11.27] 16:32:29 [IP][8846677] cmd: RCPT TO:<Receiver>
[2017.11.27] 16:32:29 [IP][8846677] rsp: 250 OK <Receiver> Recipient ok
[2017.11.27] 16:32:29 [IP][8846677] cmd: DATA
[2017.11.27] 16:32:29 [IP][8846677] rsp: 354 Start mail input; end with <CRLF>.<CRLF>
[2017.11.27] 16:32:30 [IP][8846677] rsp: 250 OK <ionel-aurelian rau <Sender>> Sender ok
[2017.11.27] 16:32:30 [IP][8846677] cmd: 5mw
[2017.11.27] 16:32:30 [IP][8846677] rsp: 500 command unrecognized
[2017.11.27] 16:32:30 [IP][8846677] cmd: fagC8ZYZRKZ8ojhdotY+lpupGajv3Bh9MaBPnJ8bZgmmVw3JoWxjubR8b1cNswte3ZnTiu++j6ZM
[2017.11.27] 16:32:30 [IP][8846677] rsp: 500 command unrecognized
[2017.11.27] 16:32:30 [IP][8846677] cmd: 7KYbAmVrPEd9vrfX6Wgz50Nl+6PhPqY/+Pyt9D3tP65Emg99QrZ2f22o7yoEhddrs/zdl6p/v1yR
[2017.11.27] 16:32:30 [IP][8846677] rsp: 500 command unrecognized
[2017.11.27] 16:32:30 [IP][8846677] cmd: tH85fDtWJJenzSvs0H8VR//3V1L6LfJRQv3vr8D7inz1deRnN+QZOhV+qZhq/EXTLyb6ehsSzjcs
[2017.11.27] 16:32:30 [IP][8846677] rsp: 500 command unrecognized
[2017.11.27] 16:32:30 [IP][8846677] cmd: 7JBd0x3qexWqJSlfn6J8Xory4hTlw2i51Xjdm2S85hSfJBrV1IVb76WPSxvx+Vapb4G3AGg3hXZp
[2017.11.27] 16:32:30 [IP][8846677] rsp: 500 command unrecognized
[2017.11.27] 16:32:30 [IP][8846677] cmd: wyOLB1HPLYCu09eePLzlcRnLhkv7W7uI92ru3fkO8/borxw9kWoF0RMgegGWdZhjs/EWS4G2u6Th
[2017.11.27] 16:32:30 [IP][8846677] rsp: 500 command unrecognized
[2017.11.27] 16:32:30 [IP][8846677] cmd: 4WFaOlEenwvVQtuwT83tHMT3f+UKbNPIs94Hl9uhx6I/f3aP8bnuNYsdsGZp7/25eAGJ+3fCPWz/
[2017.11.27] 16:32:30 [IP][8846677] Closing transmission channel: too many bad commands
[2017.11.27] 16:32:30 [IP][8846677] rsp: 421 Too many bad commands, closing transmission channel
[2017.11.27] 16:32:30 [IP][8846677] disconnected at 11/27/2017 4:32:30 PM

Apparently, with larger mails, especially those with attachements, a lot of "500 command unrecognized" occur during the SMTP session followed after "421 Too many bad commands". This never occurred before the update to Version 16.3.6535.

PLEASE HELP AS MAILS ARE NOT BEING PROPERLY DELIVERED!!!

Matt Petty Replied

11/27/2017 at 7:53 AM

Employee Post

We are working on this, and I have a build that I'm testing now that fixes the Auth Match issue. As this develops I will post more info here.

Matt Petty Senior Software Developer SmarterTools Inc. www.smartertools.com

Ionel Aurelian Rau Replied

11/27/2017 at 7:54 AM

I also posted this as a separate issue as it seems like a big bug to me: https://portal.smartertools.com/community/a89943/sm-16-large-mails-delivery-problem-during-smtp-sessions-500-command-unrecognized.aspx

Robert G. Replied

11/27/2017 at 9:11 AM

Thank you Matt

GearHost.com

Matt Petty Replied

11/27/2017 at 12:09 PM

Employee Post

We had a customer that installed this and their spool started flowing again. We've sent this out to a number of people so far and still waiting to hear a resounding "it's fixed". I will provide the build here and if it fixes the issue please let us know.

Matt Petty Senior Software Developer SmarterTools Inc. www.smartertools.com

Patrick Mattson Replied

11/27/2017 at 7:31 PM

I installed the update, stopped the service, ran the exe, and started the service again (does not appear I needed to reboot), took about 5 minutes. It asked about the web page and I enabled my security back again. Settings -> Protocols -> SMTP In -> Require Auth Match (back to Email address)

Did a test to my Yahoo email test account no issues, have been watching the spool so far so good.

Before I would get a bounce back saying email failed, but it would deliver and it stuck in the queue. My real test will be tomorrow when a customer was trying to receive a large file.

Thank you for the quick response on the update.

Alex Hee Replied

11/28/2017 at 12:57 AM

Installed this version & it's confimed working well & issue fixed. TQVM for the updates.

Alex Hee Replied

11/28/2017 at 1:56 AM

OK. It seems the bug is still there for reply email. If you create new email no this issue. Please fix it.

Ionel Aurelian Rau Replied

11/28/2017 at 6:51 AM

We`re now getting a lot of NDRs with:

The following recipient(s) cannot be reached:

      'User 1' on 
            The recipient has been deleted or has no email address.

      'User 2' on 
            The recipient has been deleted or has no email address.

which is not correct as we know their emails are running OK (one is local and another one is at GMail). Is this a connected issue?

Fadi Hussein Replied

11/28/2017 at 9:22 AM

We are planning to upgrade from 15 to 16 during the weekend, but looking at this thread; is the problem resolved or still some people facing issues with it?

thanks,

Robert G. Replied

11/28/2017 at 9:44 AM

Hold off as long as possible. Trust me

GearHost.com

Fadi Hussein Replied

11/28/2017 at 10:49 AM

going through the community threads i guess ill have to stay on 15 as you suggested. too many issues going on with v 16. thanks for the advise.

Matthew Sine Replied

11/28/2017 at 12:24 PM

The Patch seems to work for most SMTP traffic, still testing the "reply to" issue mentioned above.

We have been fielding phone calls all morning. The kicker is having to tell the customers that the inbound emails during this period are lost and they will need to contact senders to resend important emails.

To state that this bug has caused us massive problems is an understatement. Though I understand bugs, I do not understand that a bug that causes an SMTP meltdown of this magnitude was not patched immediately. We suffered only several hours with this fiasco. Others here could have been dealing with this for DAYS. This is the type of bug that can cause major defections from services provided by SmarterTools customers, and it is one more nail in the version 16 coffin.

SM team, v16 has not been a pleasant experience, to say the least, but releasing a version with this level of bug - unacceptable, period.

Thanks a lot - NOT.

Matthew J. Sine, General Manager8Dweb LLC "Making the Web a Happy Place"

Robert G. Replied

11/28/2017 at 12:43 PM

Disabling the setting in Settings>Protocols>SMTP In should fix the issue temporarily.

GearHost.com

Derek Curtis Replied

11/28/2017 at 1:38 PM

Employee Post

Alex -- we'll need some more details on this. Are you saying that when you reply to an existing, good email you're still seeing the 550 errors but with new emails you are not?

Derek Curtis COO SmarterTools Inc. www.smartertools.com

Derek Curtis Replied

11/28/2017 at 1:58 PM

Employee Post

Matthew,

Regarding the "reply to" issue that was mentioned, we're not sure the extent of that as we don't feel it's necessarily related. If replying to a corrupted message, then maybe...but a reply to a clean message should go through just fine on a patched server.

As for the spool messages, if they were attempting delivery during the issue, then yes, those would probably be blank, so yes, they'd need to be re-sent.

While we understand the extent of the issue and the problems it's caused, we DO test all builds prior to making them public. We put every build on our mail server FIRST -- the same mail server that's used for all of our emails, from our ticketing system to the mass mailings we send out. In most cases we'll catch a problem before it makes it out to the public. Unfortunately, this was not an issue we were seeing on our production server even though we send out hundreds of emails daily, and even during the period between our internal build and the one that was made public, we sent out tens of thousands of emails.

Derek Curtis COO SmarterTools Inc. www.smartertools.com

Scott Jibben Replied

11/28/2017 at 2:16 PM

Is it possible to install version 16.3.6530 or 16.3.6522 over 16.3.6535 and revert back to those previous versions?

I don't want to install a pre-release version that only fixes problems for new emails and would prefer to go back to a version that doesn't have these new bugs.

Scott Jibben Replied

11/28/2017 at 2:34 PM

SmarterTools, please REMOVE the 16.3.6535 installer from the download section of your web site.

You KNOW that it has this problem and it is horrible dealing with very frustrated customers trying to get this fixed.

Why are you STILL allowing people to download this version and causing so much pain?

Matt Petty Replied

11/28/2017 at 2:48 PM

Employee Post

Yes, you can revert to a previous version from before Wednesday's release.

Matt Petty Senior Software Developer SmarterTools Inc. www.smartertools.com

Scott Jibben Replied

11/28/2017 at 3:03 PM

Thanks, I'm using the "Major Upgrade of SmarterMail" guide because the older installer doesn't work. Anyone know how to get the 16.3.6530 version? I have 16.3.6522 but wouldn't mind getting the last working version before this update was released.

Scott Jibben Replied

11/28/2017 at 3:31 PM

I had to call SmarterTools support and specifically request this version. They are sending me an email with a link to download it. Make sure that you give them two email addresses in case your SM server doesn't deliver it.

echoDreamz Replied

11/28/2017 at 4:41 PM

This is precisely why we are waiting for this weeks release before updating from 6522 as it seems to not have this issue.

Alex Hee Replied

11/28/2017 at 5:23 PM

Derek, Yes. If created a new message with same recipient email address then no issue, but when replying same recipient email address then same error message email received.

Scarab Replied

11/28/2017 at 5:31 PM

I always keep a local copy of every Smartermail version that I install on our Mail Servers by renaming them with their Minor Version number (i.e. SmarterMail16_Setup.exe to SmarterMail16.3.6535_Setup.exe). You can't generally roll back to previous Major Versions but there have been two instances (16.3.6535 being one of them) in the past 10 years where we had to rollback to a previous Minor Version of SmarterMail and having all those older versions kept locally saved our bacon both times. Unfortunately the last Minor Version we had was 16.3.6522 and we really *REALLY* needed an item that was fixed in 16.3.6530 which is no longer available for download as SmarterTools keeps the same file name for the Installer for all Minor Versions which allows for only the latest download per Major Version available.

Looking forward to a permanent fix as our Spool came to a complete screeching halt in 16.6.6535 (which at least was a quick indicator to roll-back right away during our Scheduled Maintenance Window than let it go until morning and find out that the update went sideways after dealing with hundreds of customer calls).

Scott Jibben Replied

11/28/2017 at 9:49 PM

I usually keep a local copy of the last three versions around. However, I missed the 6530 download. If you need 6530, contact SmarterTools support and request it. I was able to get a copy that way.

Scott Jibben Replied

11/28/2017 at 10:14 PM

@Derek, where/how does this bug come into play? I couldn't figure out a pattern for it. Some Apple devices, some older Outlook customers had problems; but it wasn't everyone with these devices/software. Like you, my devices/software didn't have any problems with 6535 as far as I know, but on our backup mail server, there were many 0 byte *.eml files in the spool. The spool wasn't very busy on the main mail server either. So, I decided that I better drop back to 6530/6522 instead of moving forward at this time.

Ionel Aurelian Rau Replied

11/29/2017 at 1:02 AM

Removing v16.3.6535 from the download section would be a very good idea. Nobody should want to install that build unless they are masochistic.

James Wilding Replied

11/29/2017 at 4:19 AM

just lost 2 customers this morning due to this!

Mark Lee Replied

11/29/2017 at 7:06 AM

LOL Ionel Aurelian Rau...

Tejas Acharya Replied

11/29/2017 at 7:08 AM

16.x.6540 applied but,

Still some random issues regarding mail delivery are being faced.

how to get back to previous stable build. I still have 16.3.6493 build exe and running it give "latest version is already installed' error.

please guide.

Tejas Acharya Replied

11/29/2017 at 7:09 AM

please share download link for x.6530 if any body has.

Sirik Goossens Replied

11/29/2017 at 7:25 AM

Yes, this solved the issue.

Mark Lee Replied

11/29/2017 at 8:48 AM

Make sure you have a backup... but is simple... uninstall Smartermail and reinstall older version you want.

Tejas Acharya Replied

11/29/2017 at 9:06 AM

rolling back is only and good option. Done.

Matthew Sine Replied

11/29/2017 at 12:02 PM

My only comment to Derek's reply is that I am not sure the answer fully fits the "crime"...
We are still experiencing issues with 16.3.6540.

James, be thankful that is all you lost. 8D had a more significant negative impact with lost customers, many of whom were already tired of the SM v16 debacle.

In addition I agree with Scott's reply below. SmarterTools should have pulled the 16.3.6535 immediately after realizing there was an issue. I can see from above that there was some acknowledgement by SmarterTools as early Monday morning.

8D did not download and upgrade until TUESDAY - there is no way this version should have been left online if even 1% of customers reported this issue.

We all know this thread only contains a fraction of the number of SmarterTools customers using v16, so I do not accept that this issue is somehow "limited" as I was informed...

We have 4 copies of SM running, **all** exhibit the same problem. Some systems are dedicated some are virtualized.

We had our outbound gateway go crazy first, then **all** of our reporting systems starting puking non-deliverables to our internal mail servers, and it quickly went downhill from there.

Thankfully, we keep every single version of SM we ever download, so we too will be rolling back to 16.3.6496 after hours tonight....

I guess once the next release drops, we will wait 14 days, monitor the forums and then "read the tea leaves" before updating....

What a headache!

Matthew J. Sine, General Manager8Dweb LLC "Making the Web a Happy Place"

Barbara Renowden Replied

11/29/2017 at 2:28 PM

I just installed the 6540 patch and am still having the same issue with a handful of users. Most of the issues were fixed but those that didn't seem to have the issue are now having the issue. Very strange.

SMTP Logs after upgrade to 6540

[2017.11.29] 15:16:17 [71.201.147.140][32767822] rsp: 220 mail.centricweb.net Wed, 29 Nov 2017 21:16:17 +0000
[2017.11.29] 15:16:17 [71.201.147.140][32767822] connected at 11/29/2017 3:16:17 PM
[2017.11.29] 15:16:17 [71.201.147.140][32767822] cmd: EHLO PC
[2017.11.29] 15:16:17 [71.201.147.140][32767822] rsp: 250-mail.centricweb.net Hello [71.201.147.140]250-SIZE 104857600250-AUTH LOGIN CRAM-MD5250-STARTTLS250-8BITMIME250 OK
[2017.11.29] 15:16:17 [71.201.147.140][32767822] cmd: AUTH LOGIN
[2017.11.29] 15:16:17 [71.201.147.140][32767822] rsp: 334 VXNlcm5hbWU6
[2017.11.29] 15:16:17 [71.201.147.140][32767822] Authenticating as User@domain.com
[2017.11.29] 15:16:17 [71.201.147.140][32767822] rsp: 334 UGFzc3dvcmQ6
[2017.11.29] 15:16:17 [71.201.147.140][32767822] rsp: 235 Authentication successful
[2017.11.29] 15:16:17 [71.201.147.140][32767822] Authenticated as User@domain.com
[2017.11.29] 15:16:17 [71.201.147.140][32767822] cmd: MAIL FROM: <User@domain.com>
[2017.11.29] 15:16:17 [71.201.147.140][32767822] rsp: 250 OK <User@domain.com> Sender ok
[2017.11.29] 15:16:17 [71.201.147.140][32767822] cmd: RCPT TO: <d.dax@domain.com>
[2017.11.29] 15:16:17 [71.201.147.140][32767822] rsp: 250 OK <d.dax@domain.com> Recipient ok
[2017.11.29] 15:16:17 [71.201.147.140][32767822] cmd: DATA
[2017.11.29] 15:16:17 [71.201.147.140][32767822] rsp: 354 Start mail input; end with <CRLF>.<CRLF>
[2017.11.29] 15:16:17 [71.201.147.140][32767822] rsp: 550 From address must match authenticated address
[2017.11.29] 15:16:17 [71.201.147.140][32767822] rsp: 550 From address must match authenticated address
[2017.11.29] 15:16:17 [71.201.147.140][32767822] rsp: 550 From address must match authenticated address
[2017.11.29] 15:16:17 [71.201.147.140][32767822] rsp: 550 From address must match authenticated address
[2017.11.29] 15:16:17 [71.201.147.140][32767822] rsp: 250 OK
[2017.11.29] 15:16:17 [71.201.147.140][32767822] Successfully wrote to the HDR file. (c:\SmarterMail\Spool2\SubSpool18\402826477.hdr)
[2017.11.29] 15:16:17 [71.201.147.140][32767822] Data transfer succeeded, writing mail to 402826477.eml
[2017.11.29] 15:16:19 [71.201.147.140][32767822] cmd: QUIT
[2017.11.29] 15:16:19 [71.201.147.140][32767822] rsp: 221 Service closing transmission channel
[2017.11.29] 15:16:19 [71.201.147.140][32767822] disconnected at 11/29/2017 3:16:19 PM

Delivery Logs says the message was delivered and the end client did get the email just we keep getting bounce backs says 550 error.

Barbara Renowden President / Co-Founder Centric Web, Inc. https://www.centricweb.com

Matt Petty Replied

11/29/2017 at 2:38 PM

Employee Post

This is known, we also have a fix for it. We should be doing a release very soon, but here is a link to a custom build with the most up to date code. We've given it to a couple tickets and have seen some success in it fixing the issue.
http://www.smartertools.com/downloads/SmarterMail/CustomBuilds/16.3.6542.23003/SmarterMail16_Setup.exe

Matt Petty Senior Software Developer SmarterTools Inc. www.smartertools.com

Matt Petty Replied

11/29/2017 at 2:40 PM

Employee Post

If you download the above build, please post the success or problem if it's still occurring. We are trying to get as much feedback to make sure this is considered fixed.

Matt Petty Senior Software Developer SmarterTools Inc. www.smartertools.com

Barbara Renowden Replied

11/29/2017 at 4:20 PM

I will post back later this evening as I will need to take the server back off line again for this build.

Barbara Renowden President / Co-Founder Centric Web, Inc. https://www.centricweb.com

Barbara Renowden Replied

11/29/2017 at 7:03 PM

I just did the install and had a previous customer who was having the issue test. So far it seems to have worked. I will know more tomorrow morning.

Barbara Renowden President / Co-Founder Centric Web, Inc. https://www.centricweb.com

Matthew Sine Replied

11/30/2017 at 4:36 AM

Indeed, last evening was another round of angry customer emails and calls as the 16.3.6540 patch was still having issues... Users were receiving "sender must match..." errors, which we were able to duplicate on 1 of our 4 test machines.

8D had already planned a staged rollback to 16.3.6496. This was accomplished, but not until after the 2nd firestorm of the week.

This has been a customer relations fiasco.

Matthew J. Sine, General Manager8Dweb LLC "Making the Web a Happy Place"

Matthew Sine Replied

11/30/2017 at 7:22 AM

Installing 16.3.6543 on our internal mail server for testing... ST released around 4am this morning. Primary mail systems will remain at 16.3.6496 indefinitely since the known bugs there can be managed.

Fingers crossed.

11/30-2017 09:20am update - so far the 16.3.6543 is working well on the internal mail system. The dreaded 550 From address must match authenticated address on our internal Windows 10/ Outlook 2016 machines has finally gone away.

Matthew J. Sine, General Manager8Dweb LLC "Making the Web a Happy Place"

Scott Jibben Replied

11/30/2017 at 4:31 PM

Thank your the feedback Matthew. I'm hopeful that it has been fixed but I'm going to wait a few more days until I install it on our primary mail server.

Tom Harrington Replied

12/1/2017 at 10:45 AM

16.3.6543 resolved this issue for both servers that we run.

Alaa Majzoub Replied

12/3/2017 at 2:59 AM

I suggest you hold on, it is a dramatic change and things are not 100% perfect.

Jade D Replied

1/17/2018 at 6:31 AM

Version 16.3.6579 has this bug.

Logging ticket now with smarter tools

Jade https://absolutehosting.co.za

Tim DeMeza Replied

1/18/2018 at 9:44 AM

Bummer, any updates on this? Anyone else experiencing this? I am still paranoid to upgrade to 16. I see there is progress being made, but issues like this would kill our business.

Dennis Ryckman Replied

1/22/2018 at 11:24 AM

We are on SmarterMail Enterprise Version - 16.3.6585. Updated a week ago, and we have a customer who started complaining that he cannot send email. Looking at the logs, I'm seeing the error, 550 From domain must match authenticated domain. The user is the domain admin but his staff are able to send mail without issue.

echoDreamz Replied

1/22/2018 at 11:37 AM

Ditto, we have a ticket open, but ST is so far saying there is no issue, but we are having almost new complaints daily that Outlook just stopped working after the Dec 29th update. We had dropped a ticket that emails being sent from outlook were not having the "From Address" set correct, now after this update numerous clients are reporting they cannot send mail at all.

Employee Replied

1/22/2018 at 12:14 PM

Employee Post

We have seen many instances of this being reported. We have captured the traffic using WireShark and Fiddler between Outlook and our SmarterMail server. According to the traffiic, the client itself is sending MAIL FROM: <>. If you have SMTP Auth turned on, there is nothing against which to authenticate so it will fail. We are actively working to resolve this issue. If anyone captures different traffic, please let us know.

echoDreamz Replied

1/22/2018 at 12:50 PM

Makes no sense that Outlook with our clients has been working perfectly for YEARS then all of a sudden after we submit a ticket regarding clients complaining that emails being sent through Outlook are not setting the from address properly are now not sending at all.

Not just 1, not just 2, we have over a dozen different clients with different versions of Outlook, Windows etc. all reporting this behavior. Everything from Outlook 2003 all the way to 2016. If that is the case, why is Gmail working fine, Why are clients that are using other SMTP providers not having any other issues.

We have a client that uses us as well as another provider (they were smart and stayed on SmarterMail 15) and their other account has no issues. Same Outlook installation, our SM server is the only one reporting issues.

echoDreamz Replied

1/22/2018 at 12:52 PM

See ticket #222-21CF0DBB-0023 - After we installed this update is when we started getting reports.

echoDreamz Replied

1/22/2018 at 12:59 PM

I was able to reproduce this with my local Outlook installation. The test Outlook mesages sent without issues, normal emails sent without issues. But then when I did an email with a read recipient request, that is when my Outlook started complaining about authentication issues.

See ticket #2DA-21F13AF0-0042.

echoDreamz Replied

1/22/2018 at 1:02 PM

I would say that maybe Microsoft broke this with some update, but some of our clients are running builds of Outlook that are older than dirt and dont get updates. My test I did though, was a brand new installation of Outlook with no updates installed and I was able to get the same behavior, so it does not seem to be related to any updates. As well as I've verified with other clients that no updates were applied.

The only change to our end was the update installed for 6572. We had a report the very next day of the issue, but we figured this was just a client configuration issue until we started getting more and more reports.

Alessandro Pereira Replied

1/24/2018 at 1:36 PM

We use SmarterMail Enterprise Version: 16.3.6592
We are having the same problem with clients that use Outlook 2016

[2018.01.24] 18:07:45 [54815128] rsp: 334 VXNlcm5hbWU6
[2018.01.24] 18:07:45 [54815128] Authenticating as contabil@xxx.com.br
[2018.01.24] 18:07:45 [54815128] rsp: 334 UGFzc3dvcmQ6
[2018.01.24] 18:07:45 [54815128] rsp: 235 Authentication successful
[2018.01.24] 18:07:45 [54815128] Authenticated as contabil@xxx.com.br
[2018.01.24] 18:07:45 [54815128] cmd: MAIL FROM: <>
[2018.01.24] 18:07:45 [54815128] senderEmail(1): parsed using: <>
[2018.01.24] 18:07:45 [54815128] rsp: 550 From domain must match authenticated domain | Info: domain():n/a, authenticated username: contabil@xxx.com.br, sendersEmail:
[2018.01.24] 18:07:45 [54815128] disconnected at 24/01/2018 18:07:45

Alessandro Pereira Replied

1/24/2018 at 1:36 PM

We use SmarterMail Enterprise Version: 16.3.6592
We are having the same problem with clients that use Outlook 2016

[2018.01.24] 18:07:45 [54815128] rsp: 334 VXNlcm5hbWU6
[2018.01.24] 18:07:45 [54815128] Authenticating as contabil@xxx.com.br
[2018.01.24] 18:07:45 [54815128] rsp: 334 UGFzc3dvcmQ6
[2018.01.24] 18:07:45 [54815128] rsp: 235 Authentication successful
[2018.01.24] 18:07:45 [54815128] Authenticated as contabil@xxx.com.br
[2018.01.24] 18:07:45 [54815128] cmd: MAIL FROM: <>
[2018.01.24] 18:07:45 [54815128] senderEmail(1): parsed using: <>
[2018.01.24] 18:07:45 [54815128] rsp: 550 From domain must match authenticated domain | Info: domain():n/a, authenticated username: contabil@xxx.com.br, sendersEmail:
[2018.01.24] 18:07:45 [54815128] disconnected at 24/01/2018 18:07:45

echoDreamz Replied

1/24/2018 at 2:14 PM

Robert, any update on this?

Employee Replied

1/24/2018 at 2:24 PM

Employee Post

Unfortunately no update as of yet except that the development team is still investigating the issue.

echoDreamz Replied

1/24/2018 at 2:32 PM

Thanks Robert!

Mark Lee Replied

1/24/2018 at 8:08 PM

16 is still riddled with bugs... and they just announced 17... lets fix 16 first please...

echoDreamz Replied

1/24/2018 at 8:30 PM

It does appear to be related to SM16, the 2 SM 15 servers we manage for a client are not having this issue. At least from what we are being told and from our testing.

Nicolas Fertig Replied

2/5/2018 at 7:40 AM

We are having the same issue with Auth Match and a lot of customers complaining, since we migrated to SmarterMail 16 from 15.
After a few research we found out that the RFC specifies that a mail "From: " can be empty when sent for Read Receipt requests and were able to reproduce the problem requesting read confirmation requests.
Outlook try to send the read receipt and it's rejected by SmarterMail because the From is empty.

In a smartermail 16 changelog, I can read this:
Changed: SMTP and Delivery processes now utilize the From address in email headers if it is provided; provides better spoofing protection.

Is that the cause of this behavior change in 16. If yes, I think the feature is broken then.

Read from the interweb:
"Emails which shouldn't generate a bounce should set the empty sender in the envelope, for instance a return receipt will usually have: mail from:<> with the user's name in the from: header."

That's exactly what we are noticing in our SMTP logs for the customers having problems.

Dennis Ryckman Replied

2/5/2018 at 10:50 AM

Any updates on this, Robert? I don't see this issue mentioned as a fix in the new v17. I'm not a big fan of leaving an open relay as the bandaid. Hoping you are making progress.

IKAN Replied

2/14/2018 at 11:00 PM

I have similar issue here and also, some emails not reaching to recipient even in the same domain. Is this related to bugs in 16.x?

Patrick Mattson Replied

2/23/2018 at 6:15 AM

I did an upgrade last night, the site showed 16.3.6621, downloaded it and installed it it after installing it shows I am running 16.3.6624.

My error came back: 550 From address must match authenticated address

I have not seen this error since I did an upgrade a while back.

I think if version 17 comes out I am not going to even try it in beta, if I renew I will wait for version 18. I never had so many issues this is a support nightmare.

Matt Petty Replied

2/23/2018 at 8:36 AM

Employee Post

Is this something you are seeing a many times or occasionally, this can happen if a client tries to send in a different return-path than what they SMTP auth'd with. Could you post your SMTP log for this session with email addresses and IP's obfuscated?

Matt Petty Senior Software Developer SmarterTools Inc. www.smartertools.com

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