Email Service Monitoring

Overview

Frequently our customers want to monitor the health of their email service, which is helpful for answering support calls along the lines of “my email doesn’t work”. This is particularly valuable if you’re using a hosted email service such as Google Apps or Microsoft Office 365, but is also helpful for monitoring your on-premises messaging services such as Exchange.

We provide two distinct options for measuring email service health: Email Round-Trip Time and Email Transit Time. Note that the following instructions assume that you already have the Email_RoundTrip and Email_TransitTime DataSources in your LogicMonitor account. If you don’t have these DataSources in your account, make sure that you import them from our DataSource repository, as discussed in Keeping Your LogicModules Up to Date.

Monitoring Email Round-Trip Time

With Email Round-Trip Time our collector acts just like a desktop email client (e.g. Outlook, Thunderbird, Mac Mail, etc.) in that it sends an outgoing messages via your SMTP service and retrieves that same message from your IMAP service¹. The time to complete each step in the round-trip transaction is measured and reported, encompassing any latency within your network or in the message handoff between your SMTP service, message store, and IMAP service.

The first step in adding Email Round-Trip Time to your account is to add email_rtt to the system.categories property on a device in your account². Next you’ll need to add email service connectivity information as the following device properties:

Monitoring Email Transit Time

Our Email Transit Time DataSource measures the time it takes to deliver a message between two different email services — for example, between Gmail and Office 365³. This is particularly useful for ensuring that your email service is properly delivering and accepting messages from other service providers. Just like Email Round-Trip Time, Email Transit Time involves two protocols:

• SMTP. Sends messages from a client to a server.
• IMAP. Retrieves messages from the server to a client.

Let’s take a look at the full process for evaluating Email Transit Time using Gmail and Office 365 as an example:

1. We would use SMTP to deliver a message from the Collector to provider A (e.g. Gmail)
2. Still Using SMTP, we then give a destination address to a second provider (e.g. Office 365)
3. Finally, we use IMAP to get the message back to the Collector from Office 365

This process highlights the two critical components of Email Service monitoring: time it takes messages sent from your business’ email server to be delivered externally, and time it takes messages sent externally to make it to your inbox. Keeping this in mind, the Email Transit Time DataSource contains an ErrorCode datapoint that will denote at which stage of the above process an error occurred (if any). The following are applicable error codes:

Setting up Email Transit Time Monitoring

To apply Email Transit Time, first you’ll need to add email_transit to the system.categories property. Next you’ll need to populate connection properties for both email services (i.e. the sending service and receiving service).

In the following table, we’ve listed the seven connection properties required for both sending and receiving services, using Gmail and Microsoft Office 365 as examples.

It is essential that the “keys” used for the Gmail and Office 365 services in the device properties above (e.g. transit.gmail.smtpHost) are consistent across each service.

Finally, once you’ve added all seven necessary device properties for each service, you’ll need to create monitoring instances for each transit direction. To do so, select Add Monitored Instance from the Manage Device drop-down menu to display the Add Monitored Instance dialog. Continuing with the example Gmail and Office 365 properties listed in the previous table, fill out the fields in this dialog as follows:

In the Wildcard Value field, the colon-separated keys must match the keys used to represent the sending and receiving services.

After adding an instance for one transit direction, create a second monitored instance with the following settings to create an instance that measures the reverse direction.

Diagnostic logs for these DataSources are enabled by default, and can be found in the Collector’s “logs” directory — typically either

/usr/local/logicmonitor/agent/logs or C:\Program Files (x86)\LogicMonitor\Agent\logs.

Logs for Email Round-Trip Time are stored as:

• [hostname]-emailRTT-protocol.log
• [hostname]-emailRTT-debug.log

while Email Transit Time logs are:

• [hostname]-[instance]-emailTransit-protocol.log
• [hostname]-[instance]-emailTransit-debug.log

The Protocol logs show the underlying SMTP and IMAP commands issued by the Collector and the corresponding responses by the target server(s). You may need some expertise in the SMTP & IMAP protocols to understand what’s going on here, but frequently there’s lots of helpful information contained in these. Debug logs show telemetry of the DataSource itself — indicating what steps have been attempted and where it’s succeeded or failed.

Footnotes

¹Because this DataSource uses IMAP for message retrieval, in a Microsoft Exchange or Office 365 environment you’ll need to specifically enable access via IMAP to use this DataSource.

²These measurements will take place from the perspective of the collector assigned to monitor the device on which these DataSources are applied. Meaning: the messages are sent and retrieved from the device’s Collector rather than the device itself. You can apply these DataSources to the server your Collector is installed on (if it has been added into monitoring), or you can apply the DataSources to any other monitored device you’d like.

³When using public email services (such as Yahoo Mail, Gmail, Outlook.com, etc.) to help monitor email transit time, be aware that the anti-spam measures employed by these services may interfere with our monitoring instrumentation. Although we’ve had good luck using the Gmail service for this purpose, message hygiene services evolve over time. As such, we can’t warrant the use of these DataSources against any public service. For best results use the email service of a business partner as a third party to validate transit times.