Overview and Troubleshooting MailTips in Exchange 2010/ 2013

MailTips are useful information displayed to the end users while composing and trying to send messages to any users in their organization.

When end users select any recipient for which we have Mailtips enabled that particular information will be displayed as a tip after the GAL resolves that user in the recipient tab.

In order to troubleshoot MailTips its better we can understand the functionality of MailTips first so that it will be easier to identify and provide a fix. Let’s   see the overview and functionality of MailTips first and then we will look into troubleshooting scenarios.

How MailTips work:

  1. Sender creates a new message and addresses the message to a recipient.
  2. During message composition the client submits a GetMailTips request to the Exchange web services on the CAS server. The request is submitted as a SOAP message over HTTPS.
  3. CAS/Exchange Web Service receives the GetMailTips SOAP request and uses the information to authenticate the SOAP request and then queries:
  • Active Directory – for the requested objects (recipient, organizational).  The active directory request is executed as an LDAP query.
  • Mailbox Servers -to retrieve “out-of-office” messages, “mailbox-full” status, or any customized MailTip configured for the recipients.
  • The Active Directory and mailbox servers return the results to exchange web services.
  • The Exchange web services returns the result to the client.
  • The client will be able to see the MailTip information for that configured user account.

 

EWS is the main component for MailTips.

Mail Tips are available from client versions   Outlook 2010 and Outlook Web App as well.

Note: MailTips will not work when outlook is in offline mode.

Mail tips are triggered in the following scenarios

  • When a user resolves a recipient in the GAL.
  • When a user uses reply to all option in a message.
  • When a user adds or removes any attachment in a message.

 

Now we will look at how to configure MailTips in Exchange 2013.

MailTips is an organizational feature but still it can be enabled for each and every recipient individually as well. In order to enable MailTip for each individual we need to have MailTip enabled in the organizational level first.

We can run Get-Organizational config | fl mailtip* to see the MailTips configuration for a whole organization.

mailtip1

 

Basically we have 5 different types of MailTips in organizational level. Apart from these we have Active Directory Based MailTips which can be enabled as well. Now we will look in to the different types of MailTips and their functionality.

MailTipsALLTipsEnabled

This enables or disables the MailTip’s option totally in organizational level. If this option is disabled then MailTip functionality will not work for any users.

MailTipsExternalRecipientsEnabled

This option gives any tips to the sender if there are mail tips enabled for any user outside the organization.

Eg: Most of the organizations are much concerned about any internal confidential information should not be leaked outside for any reason. If we have this option enabled and if the user accidentally adds any external vendor, partner in a confidential trail email   he will be getting a mail tip of that information which displays that particular recipient will be shown with that custom message. This makes the sender very helpful in these kind of scenarios.

Steps to enable MailTip for external recipient

Set-OrganizationConfig –MailTipsExternalRecipientsTipsEnabled $True

When you run the above command MailTip with custom message for all external recipients will be displayed,

 

MailTipsLargeAudienceThreshold –

Gives the sender information if he adds more number of recipients in a mail than the configured threshold.

The default value is 25. We can change the value by running the below command.

Set-OrganizationConfig –MailTipsLargeAudienceThreshold <Desired Integer Value>

 

MailTipsGroupMetricsEnabled –

Displays the MailTips for the Distribution Lists and Dynamic Distribution Lists.

For example enabling this will give sender an info that the DL you are sending contains more than 100 members.

It is enabled by default. If you want to disable this feature you can run the below command.

Set-OrganizationConfig –MailTipsGroupMetricsEnabled $false

 

MailTipsMailboxSourcedTipsEnabled

This option gives the mailbox full and out of office message to the sender while he addresses message to a user whose mailbox is full or if he is out of office. This option is enabled by default.

 

Other Active Directory Based MailTips

Custom MailTips – Custom MailTip can be set for individual users with custom message by administrator.

Moderated Recipient -.  Is used to alert the sender that the recipient is moderated and that mail delivery may be delayed.

Restricted Recipient – advises that the message cannot be delivered to the recipient (when you are not in the list of users allowed to send e-mail to the recipient)

Message Size Limit – displays if the message the sender is composing is larger than configured message size limits in your organization.

Maximum Number of Recipients – displays if the sender adds more recipients than allowed. This value can be changed for each mailbox according to the configuration.

Below is an example of Custom MailTips.

In order to enable custom MailTips perform the following action.

Open EAC – Click recipients – select the mailbox for which we need to configure custom MailTips – and type the custom message and click save.

 

mailtip2

 

 

Below information is displayed for senders while addressing the message to the custom MailTip enabled user.

 

mailtip3

 

Now let’s have a small discussion in troubleshooting MailTips

 

First we need to ensure that owa is able to access the ews virtual directory without any issues. Also ensure that outlook is able to fetch the Autodiscover information.

  • First identify the MailTip issue is happening for just one user or multiple users. Also if it is will all users pick one user and start troubleshooting.
  • Check if the mail tip is not functioning in owa and outlook or any one of them.
  • Ensure that outlook is able to get the correct Autodiscover information.

 

Tools for troubleshooting MailTips

Exchange and Outlook provide tools for troubleshooting mail tip issues. Below is a listing of the tools that we can use to identify and resolve mail tip issues;

1.         Outlook 2010/2013 Diagnostic Logging (MailTips.log)

2.         Internet Information Server Logs

3.         Diagnostic Logging (Event Viewer)

4.         Performance Monitor Counters

 

 Steps to enable Outlook logging

File – Options – Advanced – Enable troubleshooting logging

Restart outlook, try to retrieve MailTips and you will get a below kind of log

You need to ensure that there is no error after GetServiceConfiguration for mailtips which is a successful transaction of MailTip.

Below is an example of successful result of a query of mailtips from outlook which shows in the outlook log.

<ex15m:ConfigurationName>MailTips</ex15:ConfigurationName>

</ex15m:RequestedConfiguration>

</ex15m:GetServiceConfiguration>

</q:Body>

 

<GetMailTipsResponse ResponseClass=”Success” xmlns=”http://schemas.microsoft.com/exchange/services/2006/messages“>

<ResponseCode>NoError</ResponseCode>

<ResponseMessages>

<MailTipsResponseMessageType ResponseClass=”Success“>

<ResponseCode>NoError</ResponseCode>

 

Similarly we can enable IIS server logging in the CAS server and look of there are any errors after get-service configuration for MailTips so that we will be able to identify the issue.

Also we can increase the following Perfmon counters for MailTips and see the results if we get any relevant information.

mm

Looking into the application logs in the event viewer will also help us in identifying the root cause.

The above troubleshooting can help us in identifying the MailTips issue.

Sathish Veerapandian

3 thoughts on “Overview and Troubleshooting MailTips in Exchange 2010/ 2013

  1. John August 7, 2014 at 10:39 pm Reply

    If you want stronger protection than MailTips has, then I can recommend an Add-in called SafeSend. It shows a popup where you have to confirm all external recipients. Link is: http://www.safesendsoftware.com

    Like

    • sathishveerapandian August 8, 2014 at 10:32 am Reply

      Hi John

      Good to see this add-in. It could be better if it has additional option like customized options mailtips as we have inbuilt in Exchange.

      Like

  2. you-cartooned.com September 16, 2014 at 1:35 pm Reply

    Hey! I know this is kind of off topic but I was wondering if you knew where I could locate
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