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Exchange 2016/Outlook 2013 - '550 5.1.15 RESOLVER.ADR.InvalidInSmtp; encapsulated INVALID address inside an SMTP address (IMCEAINVALID-)

  • 12/14/2017

Question

Thursday, December 14, 2017 5:24 AM

Hi,

Currently we are running Exchange 2016 and Outlook 2013, one of our user replied to an email, there were three recipients, the mail bounced back with the below message. Only one user received the mail. When he retried to reply to the same users the second time, it went thru. What could have caused the first email to bounce. Kindly help.

Diagnostic information for administrators: Generating server: ourdoamin.com IMCEAINVALID- Recipient1+20 Recipient1+20+3CRecipient1email+40OurmailDomain+2Ecom+3E+2C+20 Recipient2+20 Recipient2+20+3CRecipient2email+40OurmailDomain+2Ecom+3E@OurmailDomain.com Remote Server returned '550 5.1.15 RESOLVER.ADR.InvalidInSmtp; encapsulated INVALID address inside an SMTP address (IMCEAINVALID-)' Original message headers: Received: from ourdoamin.com (OurIP.51) by ourdoamin.com (OurIP.51) with Microsoft SMTP Server (version=TLS1_2, cipher=TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA256_P256) id 15.1.1261.35; Wed, 13 Dec 2017 15:32:33 +0400 Received: from ourdoamin.com ([fe80::11b6:61b7:827f:6ca3]) by ourdoamin.com ([fe80::11b6:61b7:827f:6ca3%21]) with mapi id 15.01.1261.036; Wed, 13 Dec 2017 15:32:33 +0400 Content-Type: application/ms-tnef; name="winmail.dat" Content-Transfer-Encoding: binary From: Sender Name To: "Recepient 1 Name, Recepient 2 Name " 　　　　　　　 CC: recipient 3 Subject: RE: OurSubject. Thread-Topic: OurSubject. Thread-Index: AdNyfvxhazQF6OArTWWkQmkzpNlwwAABenzAACf5WpAABZYPsAAAj9twAASsC1AAHM0ZYAADPh4wAAC5ZjA= Date: Wed, 13 Dec 2017 15:32:33 +0400 Message-ID: <4ce7e75a6be54b6a80c636e6f444657d@OurmailDomain.com> References: <7c0489c7f8a145849f0d3f6fb80dcc16@OurmailDomain.com> <6372d1df8f9d418b92e598c5a9758e33@OurmailDomain.com> <8e7b4ca4a12b41bc9213c1ea6ee1a87e@OurmailDomain.com> <3365c46a84d44d82bc387451bf757216@OurmailDomain.com> <8de080342f45435289fe7b56335bf7ca@OurmailDomain.com> <7a0f56b85421405281c72ae9a14a4789@OurmailDomain.com> <223495bb744f47faba4f7c21edc561aa@OurmailDomain.com> <7622f9cc655b48489454cf870423083b@OurmailDomain.com> In-Reply-To: <7622f9cc655b48489454cf870423083b@OurmailDomain.com> Accept-Language: en-US Content-Language: en-US X-MS-Has-Attach: yes X-MS-TNEF-Correlator: <4ce7e75a6be54b6a80c636e6f444657d@OurmailDomain.com> MIME-Version: 1.0 X-Originating-IP: [NLBIP] Return-Path: senderemail@OurmailDomain.com

All replies (15)

Friday, December 15, 2017 3:15 AM

Hi Ahamed,

For the returned error '550 5.1.15 RESOLVER.ADR.InvalidInSmtp; encapsulated INVALID address inside an SMTP address ", the issue may be related to the invalid SMTP address for recipients.

I notice that the issue happens when reply an email to three recipients. Have you tried to directly send new test emails to these three recipients?

In Outlook, please click New Email, type recipients email address to To field without using any caches, then send out the email to confrim if it can be sent successfully.

Also try to reply the email in Outlook Web app, check if the issue persists.

Regards,

Winnie Liang

Please remember to mark the replies as answers if they helped.
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Sunday, December 17, 2017 1:00 PM

Hi Winnie,

Thank you very much for your response.

As mentioned in my initial post, the second time the user replied to the same email it went thru. If it was caching issue emails should never go thru those users until the cache is deleted, we are not able to recreate the issue again.

Regards,

Ahamed

Wednesday, December 20, 2017 10:19 AM

Hi Winnie,

Thank you very much for your response.

As mentioned in my initial post, the second time the user replied to the same email it went thru. If it was caching issue emails should never go thru those users until the cache is deleted, we are not able to recreate the issue again.

Regards,

Ahamed

Hi Ahamed,

I notice you mentioned that you are not able to recreate the issue again. Do you mean there is no issue currently?

Any further help is needed?

Regards,

Winnie Liang

Please remember to mark the replies as answers if they helped.
If you have feedback for TechNet Subscriber Support, contact tnsf@microsoft.com.

Tuesday, January 23, 2018 7:47 PM

I am having the exact same issue. Sending the first time fails with same error. sending again from sent items goes through.

Friday, October 5, 2018 8:17 AM

Is this issue still current? I have the same issue with a customer. I let him clean the auto-complete list to see if it helps...

Please update the thread if the error still persists?

Thanks in advance,

Joost Brenters

Tuesday, February 19, 2019 10:41 AM

Hi,

I have almost the same problem, when I create a new email from our ERP.

Steps:

  1. In the ERP software I select my customer and make click on "Send mail"...
  2. The click open an new Outlook email message with the customers email-address, subject and text...
  3. I save the message in my drafts
  4. Later I reopen the message, click to send.
    5. I receive a email with the error description above (550 5.1.15 RESOLVER.ADR.InvalidInSmtp ……...)

If I do not save the mail and send it directly there is no problem.

I use Office 365 Build 1901 with Exchange 2016 with last updates.
This only happens with Outlook in online mode. We use Outlook on terminal Server.

Thanks
Michael

Thursday, February 28, 2019 12:32 PM

Hi, we having the same issue, with outlook 2010/2016 after migrating from Exchange 2010 to 2016 on premises.

Did you managed to solve the issue?

Kind regards,

Peter

Thursday, February 28, 2019 12:40 PM

No, unfortunately, no solution.

I will soon install Exchange 2016 CU12 and see if the problem still exists.

Kind regards,

Michael

Monday, March 11, 2019 11:40 AM

We have the some issue with one of our customers.

We use Outlook 2019 (updated) on Windows 10 x64 (updated)

Exchange 2016 CU10

Alexander Neunsinger Owner MY-IT.WORKS UG Hallerstraße 32 90419 Nuernberg Germany

Thursday, April 4, 2019 6:03 PM

I am having exaclty the same issue with Outlook 2016 on Windows 7 or 10 with Exchange 2016 CU10.  Is there any fix?

Come on Microsoft, can't you see people are struggling?

Thursday, April 4, 2019 6:05 PM

Much_r

Did it fix it?

Saturday, April 13, 2019 3:44 PM

Hello All,

We are having the exact same problem...

If we send directly the email, it works but if we save it first in the drafts or any other folder to send the email later, it does not work...

It seems that Exchange Server is adding our domain at the end of the address email, so it is true that it is an invalid address email.

But before we send the email, the address email is correctly written in the "TO" section. It's after pushing the button "SEND" that Exchange Server adds our domain at the end...

It's been a week that I'm looking for help, and i found none...

It could be great if someone could help us out with this matter.

I will try to post something in another section of the forum.

Please help us solve the problem.

Thanks a lot

Tuesday, June 4, 2019 11:19 PM

We are having the same issue as well. We are using Exchange 2016 CU10 and Outlook 2019 on Windows 10.

Wednesday, June 5, 2019 6:38 AM

Hello,

Sorry for my late reply.

I have now installed Exchange 2016 CU 12 and the problem still exists.

I suspect that Microsoft will not solve the problem .....
Unfortunately, this is nothing new, the problems are not solved.

greetings
Michael

Friday, January 24, 2020 1:09 PM

I just had this problem and I have solved it. In my case (I don't know if it will happen in the rest of the cases) the user who sends the mail has a special or strange character in the system. In my case, I am from Spain, the user had a Ñ in his last name. Removing it has already worked.