Troubleshooting Outgoing email issues
To do this, we need to reference the mail flow diagrams shown in the Explanation post previously. We’ll first cover the Outgoing portion of the Email Router.
Troubleshooting Outgoing email issues is the not a difficult part of the Email Router to troubleshoot. The reason is that there are only two different configuration options, SMTP or Exchange Online. Realistically, you troubleshoot these the same way. Obviously we have some restrictions during the troubleshooting steps when working with Exchange Online but these should be pretty obvious. Let’s go ahead and get into troubleshooting at this point.
The first thing to know about troubleshooting the Email Router is to remember the traffic flow. This was shown in the second post of this series but I have included it here as well:
Each step represents a potential break point. The key to troubleshooting is to understand where the error occurs and what the error is telling you. So how can we determine where the issue lies?
The first step to this is to understand, what’s the state of the email within CRM? There are three status the email can be when in CRM.
- Pending Send
What’s an easy way of understanding what emails are in which state? The typical recommendation I have made to our customers is to use Advanced Find on the E-mail Messages entity. When building your Advanced Find, you will want to ensure you have, at minimum, the following columns: Subject, From, To, Status Reason, No of Delivery Attempts.
Note: The one thing I want to ensure is pointed out is the last column of No. Of Delivery Attempts. This tells us how many times the Email Router has tried to send the email. Anytime it goes from Pending Send to Sending, it increments this attempt by 1. We delay sending emails that have higher Delivery Attempt counts.
Each of the email statuses signify a different step within the mail flow diagram above. Let’s review each of these now:
- Pending Send: Pending Send means that the email router has not processed this email message yet or there was an error when it did process it and put it back into a pending send status to try to send it again at a different time. The key to knowing how to differentiate these is to look at the Advanced Find.
One Pending email with the Subject of “Failing Email” shows that the router has tried sending the email five times and it’s still unable to do so since the Status Reason is still Pending Send. This tells me that there is an issue between the Email Router and the Outgoing service (SMTP or Exchange Online). The email router was able to retrieve the message from the CRM server, validated the user information within CRM, and submitted it to the Outgoing service to be delivered. For some reason, the outgoing attempt failed for this email and I can review the Event Viewer Application Logs for more information. The other email in a Pending Send state, shows the delivery attempts as 0. This means the router has not yet picked up this email for processing. This could be due to quite a few reasons.
- The User’s profile does not list E-mail Router in the Email Access Configuration for Outgoing:
- The user is not listed in the Email Router Configuration Manager after clicking on Load Data:
This could be due to the Email Access Configuration for the user not set to Email Router for Outgoing or the user’s email address has not been approved.
- The user does have Email Access Configuration set to Outgoing and is in the Email Router Configuration Manager but the user’s GUID <UserId> is not present in the Microsoft.Crm.Tools.EmailAgent.xml file:
In this case, the user’s GUID is B8DD579B-501D-E211-AA2E-00155D51F43. The reason could be that after the user’s settings were changed to Email Router (Email Access Configuration) no one went back in the Email Router Configuration Manager and clicked on Load Data and Publish.
- The user’s Personal Options do not allow the Email Router to do processing on their behalf.
The setting for “Allow other Microsoft Dynamics CRM users to send e-mail on your behalf” is needed for those that generate emails and change the from field to use your account.
The setting “Allow E-mail Router to use my credentials to send and receive e-mail on my behalf” is required when the Outgoing profile within the Email Router Configuration Manager is set to User Specified for Access Credentials.
- Sending: Sending means the Email Router is currently processing the message. It has already accepted it from CRM and is currently waiting for the Outgoing service to accept the message. A failure here would send the email back into a Pending Send status and then Delivery Attempts would have been incremented. If the issue is occurring at this step, then you are going to need to use some additional tools suggested below in the “Outgoing Protocols” section.
- Sent: This means that the Outgoing service has accepted the email for delivery and now it is up to the Email service to get the email to the To and CC addresses.
We also need to understand the protocols being used for the Outgoing profile. Each scenario dictates different types of tools and troubleshooting:
The main troubleshooting tool we will use for troubleshooting SMTP issues is some sort of network sniffer such as Microsoft Network Monitor (NetMon) or WireShark. Being the company man that I am, let’s take a look at what NetMon will show us.
By adding a Filter of “ProtocolName == “SMTP”, I can easily see all of the SMTP traffic. Now the error the
problem email is the following:
Looking through the traffic, I can see that the Exchange server, for “some reason” is throwing Reset packets:
By looking at the NetMon traffic, I knew the issue was coming from the Exchange server and there must be some sort of configuration problem on that particular server. If the issue was intermittent, maybe it was one of the servers in the environment having problems. After doing further troubleshooting, it was found that, the firewall on the Exchange server was blocking the traffic from the CRM server.
Exchange Online is using Exchange Web Services (EWS) to send emails. In this case, we can use Fiddler to see what the response coming back to CRM is.
Additionally, we can use a tool called EWSEditor found on CodePlex. EWSEditor allows us to emulate the same requests as what is being done by the Email Router. In the screenshot above, you can see that CRM is making an EWS call to GetFolder. You’ll notice that the Email Router is going to use the schema version for Exchange 2007 SP1, just a tip when using EWS Editor. We’ll get into the actual usage in a tools post here.
The next part of this post is to cover Troubleshooting Incoming email issues.