The Irritation of Exchange Online’s Inconsistent Mail Tips

Little Things (Like MailTips) in Exchange Cause Irritation

Sometimes Office 365 drives me up the wall. It’s usually when little things don’t work like they should rather than problems with big pieces of functionality. The different ways that Exchange Online and clients handle MailTips is a current irritant.

Usually I don’t think too much about MailTips. They’ve been part of the product since Exchange 2010 and usually don’t cause any fuss or bother. Recently, Microsoft introduced a new tip in Outlook Mobile to warn users when they add a recipient to a message who’s outside the tenant. It’s a good idea that isn’t dependent on the transition to the new connection protocol for Outlook mobile, unlike many of the new mobile features Microsoft hopes to deliver in the future.

But curiously, Outlook for iOS shows different warnings depending on how the MailTips settings in Exchange Online’s organization configuration are set. On the left, we see the warning shown when the setting to disable MailTips is set, on the right, the different warning that appears when the setting is enabled.

Outlook for iOS shows different warnings when MailTips are enabled or not
Outlook for iOS shows different warnings when MailTips are enabled or not

The external recipient warning is the only one of the MailTips supported by Exchange Online displayed by Outlook Mobile.

Organization MailTips Configuration

The controls to turn MailTips on or off are in the organization configuration and can be set by running the Set-OrganizationConfig cmdlet. In this case, the settings of interest are:

  • MailTipsAllTipsEnabled: Enable or disable Mail Tips. The default is True.
  • MailTipsExternalRecipientsTipsEnabled: Enable or disable the tip that a message is going to an external addressee. The default is True.

Although I can’t think of any good reason to disable the warning for external recipients, it doesn’t seem right for Outlook Mobile to ignore a perfectly good setting. After all, if a setting can be set to False, then the clients that are supposed to respond to the setting should do so. The reason might lie in the fact that Outlook Mobile supports a setting to control the display of the external recipient tip in its application configuration policy. That is, if you use Intune.

Another setting (MailTipsLargeAudienceThreshold) allows an organization to set a threshold for a large recipient list (25 is the default) to warn someone when they’re about to send a message to a large group. The original idea was to warn people when they addressed messages to large distribution lists. And another (MailTipsMailboxSourcedTipsEnabled) controls whether warnings appear when people are out of the office or their mailbox quota is exceeded.

Outlook’s MailTips Settings

Possibly for historic reasons (because these settings go back to Outlook 2010), Outlook has its own controls for MailTips. Go to Options, Mail, and find the MailTips section. You can choose to never see MailTips or the selection of MailTips you want Outlook to display.

The MailTips options in Outlook for Windows
The MailTips options in Outlook for Windows

Neither OWA nor Outlook Mobile offer the same degree of control over the display of MailTips.

Differences in OWA

OWA doesn’t offer the same control over MailTips as Outlook does. Apart from this, the only issue I have with OWA is that the “new” version of OWA doesn’t display a warning if a message exceeds the 25 “large audience” threshold. Given that we’re in the middle of a transition between client versions, this is probably an oversight that Microsoft will address before they switch everyone to the new version.

MailTips in the old version of OWA (including a warning about recipient count)
MailTips in the old version of OWA (including the large audience warning)
MailTips for the same message in the new version of OWA (no warning about recipient count)
MailTips for the same message in the new version of OWA (no large audience warning)

Commonality Across Outlook Family

I’ve no doubt that some will be unaffected or won’t care about the variation in treatment of MailTips that exists across the Outlook clients. The fact that Outlook has its own set of controls doesn’t bother me, but I am irritated that the clients don’t all handle MailTips in the same way. It seems that Microsoft could do a better job of smoothing the differences across the different clients.

Note that it can take some time before changed settings in a tenant’s Exchange Online organization configuration become effective. OWA usually picks up changes first followed by Outlook and Outlook Mobile.

We try not to show irritation in the Office 365 for IT Pros eBook. That’s why we have this blog – to share some of the feelings that we otherwise hide.

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