Enable MailTips Office 365

MailTips is helping you to avoid mistakes or be aware of where email goes or just adding a warning before sending the email.

For example:

My boss, SMTP address is [email protected], if you be mistake type “Boss@pelegiit.co.il” you will receive MailTips message that means this recipient CEO or CIO or another way you can set it that this mailbox  is external recipient and not internal, This is one of the mail tips abilities or take it to another way of if you try to reply to HR distribution list you get TIP of this recipient is contains 1000 recipients so

In short words, mail tips are very necessary.

How can we enable it?

First of all, we have to connect to our Office 365 environment using Powershell:

You can review my article which explains to you how to connect to Office 365:


Login to Office 365 automatically with encrypted password


$UserCredential = Get-Credential
$Session = New-PSSession -ConfigurationName Microsoft.Exchange -ConnectionUri https://outlook.office365.com/powershell-liveid/ -Credential $UserCredential -Authentication Basic -AllowRedirection
Import-PSSession $Session

Once you are connected you have to run the followings:

Set-OrganizationRelationship -id “XXX” -MailTipsAccessEnabled $True -MailTipsAccessLevel all



You can also create specify mail tips for specific Mailbox, for example:

Set-Mailbox “[email protected]” -MailTip “System Administrator”