Why is my message taking so long to arrive at its destination?

Scenario: You sent a message from your Office 365 mailbox.  One or more recipients are complaining either that they haven’t received the message or that the message took a long time to arrive.

 

Steps:

  1. Open a delivery report for your message
  2. Evaluate the report
  3. (Enterprises & Education only) Track the message through FOPE
  4. Reach out to the receiving side if necessary

 

1. Open a delivery report for your message

If you have Outlook 2010, go to your Sent Items folder, and find the message you want to track.  Open the message.  In the message window, click the File tab.  Under Message Delivery Report, click Open Delivery Report.

 

 

If you are using anything other than Outlook 2010 to send your messages, you will need to go to Outlook Web App (OWA).  In your Sent Items folder, right-click the message and choose Open Delivery Report.

 

Note: This option is not available if you right-click a conversation. First, expand the conversation and right-click the actual message.

 

As an administrator or someone with the ability to track messages (helpdesk), you can also search directly from the Exchange Control Panel. From OWA, choose Options then go to Manage my Organization; or from Office 365 portal, go to the Admin page and select Exchange or Outlook. 

 

Once in Exchange Control Panel, select Manage My Organization in the Mail Control tab.  

 

  

2. Evaluate the report

For each recipient, the results will look something like this:

 

 

Note: Exchange Online currently only keeps message tracking data for 14 days.  If your message was sent outside of that time period, you will not be able to run a delivery report.

 

The main things to look for are the following:

  • Was the message successfully submitted?  Does the time stamp match what you expected?
  • If sent to an Office 365 recipient, was the message delivered?  If yes, what was the delay from the submit time?
  • If sent to a non-Office 365 recipient, was the message transferred (handed off to a different email system)? If yes, what was the delay from the submit time?

If there was a significant delay between the submission event and handoff or delivery, then the problem may have been with Exchange Online.  Otherwise, the investigation takes us elsewhere.

 

After leaving Exchange Online, the message is then handed off to Forefront Online Protection for Exchange (FOPE).  If you have Office 365 for Professionals & Small Business, then skip to Step 4.

 

3. (Enterprises & Education only) Track the message through FOPE

At this point, if you’re an end-user, you need to get your tenant administrator involved.  If you’re an administrator, you need to know if you have an Enterprise or Professional/Small Business plan.   You can only perform this step if you have Office 365 Enterprise.  For a description of what Forefront Online Protection for Exchange (FOPE) features are offered by plan, see the feature comparison.  If you have Office 365 for Professionals & Small Business, then skip to Step 4.

 

In Exchange Control Panel, on the Mail Control tab, click Forefront Online Protection for Exchange.

 

Note: If you get an error that your session has expired, you may need to close your browser, open a new browser session, and re-authenticate with Office 365 to access the FOPE Administration Center.  Occasionally, being logged into a Microsoft Live property may also cause a problem.  Either log out and close all browser windows, or open an “in-private” session which will temporarily disable using your existing cookies.

 

Once logged in, click the Tools tab and then click the Message Trace tab.

In the Message Trace tool, enter the search parameters – in this case, enter the sender and recipient addresses.
 
Note: Exact addresses are marked out for privacy, but the entire SMTP address is required.

 

After retrieving results and clicking Details, you’ll see more information like this in the Message Trace Summary:

 

The important values to make note of are as follows:

  • The To IP address field, which shows you the IP address to which FOPE attempted to deliver the message.  You can use a tool like Exchange Remote Connectivity Analyzer or NSLookup to see if that IP matches what you expected, or if perhaps there might be a DNS or FOPE configuration issue.
  • The Filtering results field, which indicates if FOPE determined that the message was spam or malware.
  • The Delivery result field, which indicates if the message was handed off or not.

Note: The From IP address is the address of the Exchange server in Office 365 that handed the message off to FOPE.  In the outbound message case, this probably is not important.

In this case, there was a permanent failure (5xx is permanent and 4xx is temporary, which would lead to a delay and maybe an eventual timeout).  A Delivery Status Notification (DSN) should have been issued to the sender, which is covered in more detail in How do I interpret a Delivery Status Notification (DSN) message?

If FOPE received the message and appears to have attempted delivery, in most cases the next step is to understand if the next system received the delivery or not.  In either case, however, it may be necessary to run troubleshooting and tracking tools on the receiving end to determine the reason for failure.

4. Reach out to the receiving side if necessary

Assuming that you still have not solved the issue with the data you've collected, this is about as far as you can go right now from the sending side.  If you just sent your message, you will need to give it some time to arrive or timeout.  If the message times out inside of FOPE, then you will get a notification and be able to skip to the troubleshooting notifications section.  If, however, you do not receive a notification, then you should contact the receiving side to have them perform message tracking.  You will need to provide them with To and From information, as well as an approximate Date and time.  In most cases, the remote side should be able to provide you with information to help you make sure your message got past their anti-spam defenses, when it was received, and if it was delivered.

 

Common problems

Here we'll add links to helpful Knowledge Base articles or other documentation that pertains to this scenario.

  • If you are having trouble sending mail to certain domains, you may want to verify that you have the recommended DNS record types for sending mail.  Specifically, you want an A record for the domain (example: @.contoso.com - this record should generally point to the same address as your www record), an MX record, and SPF record that designates Outlook.com as a sender.  For more information see Domains in Office 365.