The following articles were included in our Exchange Messaging Outlook (EMO) newsletter published on March 13, 2025.
EMO is a weekly publication. To receive your own copy of EMO by email, subscribe here.
Support Exchange Messaging Outlook Sponsors
Increase Your Productivity!
ReliefJet Essentials for Outlook is a set of more than 160 tools for performing a wide range of tasks in Outlook: processing email messages, contacts, appointments, meetings, tasks and other Outlook items.
Today's Highlights »
You don't often get email from….
A user wondered about a banner at the top of a reply message that said “You don't often get email from [address].”
This message is a first contact safety tip in Microsoft 365 business accounts, letting the recipient know that maybe they shouldn't trust the message. It’s most useful when the sender’s name is the same as a friend or coworker, alerting the recipient that it’s not from the address the person normally uses.
This is an anti-phishing policy setting in the Security and Compliance center and can only be removed by the admin. (When a person replies, they could edit the reply to remove it, but most people won’t bother.)
It's supposed to be shown the first time you receive a message from a sender and when you rarely receive mail from the sender. If you regularly email with the person, it will eventually stop being added to your messages.
To remove it, the admin needs to change the anti-phishing policy settings for Safety tips. They would uncheck the option for “Show first contact safety tip (Recommended)”.
Other safety tips include “Show user impersonation safety tip”. This adds a banner that says “This sender appears to be similar to someone who previously sent you email but may not be that person.” This could prevent someone from falling for a phishing scam from a familiar name. For example, I see this banner a lot when I send test messages from accounts where my display name is “Diane Poremsky”. (Yes, I should change the display name on some of the test accounts.)
The “Show domain impersonation safety tip” is shown to recipients when the sender's email domain is included in domain impersonation protection. The banner reads "This sender might be impersonating a domain that's associated with your organization."
To use the domain impersonation safety tip, the admin needs to enable Domain impersonation protection and enable protection on the domains in the tenant or domains that belong to partners and other domains you do business with.
When the sender's name or email address contains characters that aren't typically used together, the “Show user impersonation unusual characters safety tip” will warn the recipient. For example, if the name or address contains a mix of mathematical symbols and plain text or a mix of uppercase and lowercase letters. For what it's worth, I have this enabled and have never received a message this was applied to. (It’s possible the junk mail filter finds the messages first. )
The admin can get to the anti-phishing policy using this link: https://security.microsoft.com/antiphishing or from the Microsoft 365 admin center:
1. Open the Security admin center
2. Expand the “Email & collaboration” section then select “Policies & rules”.
3. Choose Threat Policies then Anti-phishing.
4. Select the anti-phishing policy that is in effect. This opens a panel on the right side.
5. Scroll to the bottom of the Actions list and click Edit actions.
The Safety tips are at the bottom.
While the first contact tip can be annoying, especially if you receive a lot of mail from outside your tenant, the other settings can alert users to phishing mail and should be left enabled.
Microsoft Account Password Changes
Microsoft will require users to create a new password if they suspect a hacker has attempted to log into the Microsoft account. (When it happened to me, it was me trying to log in.)
But if a Microsoft account user wants to be forced to change their password frequently, they can opt-in to require a password change every 72 days. The option is on the password change page at https://account.live.com/password/Change
Whether this really makes your account more secure is questionable, especially if you use a variation of the same password (such as changing the last characters of the password).
Better is to use a strong password that is only used to log into the mailbox and enable 2-step verification. You should also never use the password with another account, especially to log into other websites.
If you want to increase security on the account (or have a lot of sign in attempts in the activity list) you can add a new alias to your Microsoft account, set it as primary then remove sign in permission from the current address. If you only use the address to sign into email, hackers will never discover it, and it is less likely to be exposed in a data breech.
If you only use Outlook on the web for email you can set a default address in View tab > View settings > Mail > Forwarding and IMAP
However, if you open your mailbox in a mail app, you will need to select the desired From address every time you send new mail. Replies should be sent from the address that received the message.
Add an alias here - https://account.live.com/names/manage
DO NOT REMOVE THE CURRENT ADDRESS! If you do, it is gone forever. You only want to add a new alias and set it as primary.
Change sign in preferences using the link at the bottom of that page - https://account.live.com/SignInPreferences
I have screenshots in this article: Keeping Hackers out of Microsoft accounts
Delay Send Email
A user asked “Is there a way to send a mail after a certain time in outlook?”
Sure. How you do it depends on which Outlook client you’re using.
New Outlook, Outlook on the web, and Outlook for Mac:
Click on the Send button to expand the menu and choose Schedule Send. Pick the date and time then click Send. The message will stay in the drafts folder until the appointed time. Because the message is stored on the server, the message will be sent even if Outlook is not open.
Classic Outlook for Windows has two options to delay sending messages: an after sending rule that holds a message in the Outbox for up to 120 minutes or a setting in Message Options to send the mail at a specific time. Note that because the message is held in Outlook, it needs to be open to send the message.
If you want to pick the time and date to send the message, use Outlook’s "Do Not Deliver Before" option. Outlook will hold the mail in the Outbox and send it at the date and time you selected but only if Outlook running.
If you use Exchange server mailbox and are in online mode, not cached mode, the message is moved to the outbox on the server, allowing you to close Outlook.
To hold messages for up to 120 minutes, you need to create an "after sending" rule. This rule can apply to all messages or only to messages that meet the conditions you set.
Open the Rules Wizard and click New rule.
1. Select Apply rule on messages I send (at the bottom of the first Rules Wizard screen)
2. Select any conditions you want and click Next or just click Next to apply it to all messages you send
3. Choose Defer delivery by a number of minutes at the bottom of the Actions list.
4. Click on the "a number of minutes" link to select the desired number of minutes to hold the messages.
5. Click Next and set up any desired exceptions, then click Next again.
6. Enter a name for your rule, turn the rule on and click Finish to finalize the rule.
To delay sending a message in classic Outlook
New & Updated Microsoft 365 & Exchange Server Support Articles
Introducing Exchange Online Tenant Outbound Email Limits | Microsoft Community Hub
New & Updated Outlook Support Articles
Sync your account in Outlook to the Microsoft Cloud
Feature comparison between new Outlook and classic Outlook
Outlook icon on the Start menu is not updated to Outlook (classic)
Classic Outlook mail merge hangs trying to initialize Word
[INVESTIGATING] Go back to classic Outlook button not working correctly in new Outlook
Other Resources
Fixes or workarounds for recent issues on Outlook.com
Import EML Files into New Outlook
How to import EML files into new Outlook for Windows.
Insert Word Document into Email using VBA
How to use a macro to reply to senders by inserting the text from a Word document as the message text. There is also a macro to send a new message with the contents of a Word document inserted.
New Outlook: Show To, CC, BCC in Replies
When you Reply or Reply All in new Outlook, the CC line is not visible, even if the message was CC’d to others. If you reply all, you may only see one name and "+ Others". I'll show you how to view all addresses and the CC and BCC fields.
Opening PST files in New Outlook
How to open a PST file in new Outlook and the current limitations.