Internet message id differs in Sent and Inbox item when Outlook connected to Exchange in OnlineMode

Question

Hi!

When Outlook is working in online mode (not cached), interenet message id is broken during sent. When I check internet message id (PR_INTERNET_MESSAGE_ID_W) in Sent folder and for the same item in recepient's Inbox folder it is different. Sent time is also different and can differ up to 10 seconds and once it was even 10 minutes! Even in the simplest case when I sent a message to myself breaks.

There is KB924213 that describing a similar issue. It is deleted, but can be found here:
https://www.betaarchive.com/wiki/index.php/Microsoft_KB_Archive/924213

But the situation even worse than described there. It does not work in online mode and:
"In Online mode, when you send a message, it is submitted to Exchange and then stamped with PR_INTERNET_MESSAGE_ID. The copy in your Sent Items and the received item in your Inbox contain the same PR_INTERNET_MESSAGE_ID because they originated from the same message."
is not true.

Tested on different Exchange versions (2013, 2016) - the issue is the same. Outlook is from Office 365.

Any clues why it is broken? Any workaround for this? The only way to identify that this is the same e-mail is PR_SEARCH_KEY, but we get info about the message from the document management system which does not contain such info. They also rely on internet-message-id.

Answer 1

Hi @Sergey Belikov ,
In order to better solve the issue, I need to ask some questions.
1.Only one user have this issue or all users have this issue?
2. Is your Exchange environment separate Exchange 2013 and Exchange 2016 or does Exchange 2013 and 2016 coexist? What is the specific version?You could run the following command to view the Exchange version.

Get-Exchangeserver | fl *version*  

3.Which server are the sender and recipient on?

According to my test in Exchange 2016, the message sent/received in Online mode and viewed in Online/Cache mode - PR_INTERNET_MESSAGE_ID is present on message in Sent Items and is the same as PR_INTERNET_MESSAGE_ID of the message in the Inbox. The following is my specific test in the test environment, I send a email from Administrator to user1, and view the PR_INTERNET_MESSAGE_ID by MCFMAPI. Found that the values are the same.

Please following the steps and see if the issue is resolved:
1.Please check if there have any transport rules that could change the message id.
2.Please try to run “outlook.exe /safe" in “Run” to start Outlook in safe mode. Safe mode will disable the add-in in outlook, in order to exclude the possibility of third-party add-in causing this issue.
3.Please send a test email and then run the following command to check message id in message tracking log. Check whether the message id changes during internal delivery.The screenshot below is my test in lab.

Get-MessageTrackingLog -Server Exchange2016 -Start <> -End <> -Sender <> | fl messageid,eventid,source  

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Answer 2

Hi @Sergey Belikov ,

1. According to the information, you mean that this issue only occurred during you send an email to yourself in Outlook online mode. Please correct me if I understand it wrong.
2. Based on my knowledge, you are correct, the Message ID is generated by the mailbox system, which is Exchange server. When Outlook is in Online mode, it will always be connected to the Exchange server. According to my test, it is the same as the article you provided. Sending or receiving emails in Online mode can be viewed the same "PR_INTERNET_MESSAGE_ID" on both sent and received emails. If you sending or receiving emails in Cache mode, you couldn’t view the “PR_INTERNET_MESSAGE_ID" on send mail in Cache mode.
   This article will help you better understanding : Comparison of Cached Exchange Mode and Online Mode
3. What is the query result of sending a test email and running the above command line? Did the parameter "Message ID" changed during the delivery process?
4. You could send a test email, and then put the email header into the Message Header Anaylzer in ExRCA for analysis. The analysis result will show the routing information of the mail during transmission.
   About ExRCA: Microsoft Remote Connectivity Analyzer
   

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Answer 3

1. On Exchange 2013 yes, it is stable reproduced only when I sent message to myself. On Exchange 2016 (Exchange Server 2016 CU15December 17, 201915.1.1913.515.01.1913.005) it was reproduced once when sending to another user on the same server, but selfsend is working ok even in online mode with the same Outlook client (using different profiles to check).
2. Actually, in cached mode internet-message id also appears on sent item on the next synchronization with Exchange. But we can see it in online mode or bypassing the cache. Anyway, currently, we are trying to make it work properly in online mode.

I checked the article you provided, but want to know how it is handled inside Exchange. When it sets internet-message-id, how and when sent-time transformation happens, which optimizations uses when message sent between users on the same server? I was not able to find such info.

I have also tested selfsent on Exchange 2013 using OWA. In this case, it is the same. So this looks like Outlook/Exchange combination issue.
Outlook version is Outlook for Microsoft 365 16.0.13127.20266 32-bit.
But our clients using Outlook 2016 and we need to support it also.

Regarding command line checks, will try to contact our admins to test.
Nothing interesting in headers. See picture.

Answer 4

New info. We were able to reproduce this again when sending between users on the same Exchange. But this time with Exchange 365 (15.20.3391.14). In Outlook cached mode works ok, in online internet-message-id changes. Both Outlook users are in online mode.

Answer 5

@Sergey Belikov We finally got a solid answer from Office Support, which I'm sure some will be interested in:

please note that we acknowledge the behavior and that is indeed a known behavior that will not change for the time being. When we have a primary account in Online Mode and we then add a secondary account to the same Outlook profile, then the PR_INTERNET_MESSAGE_ID will be different when comparing same message from Sent Items and the message from recipient side. This issue is due to the fact that in the above configuration we are using a different type of Send operations and the properties on the message are stamped differently by the server. To conclude the behavior is known and will not change for the time being due to vast architectural design changes that need to happen.