Volume 28 Issue 21

Issue Date: September 21, 2023 « Previous Issue | Next Issue »

The following articles were included in our Exchange Messaging Outlook (EMO) newsletter published on September 21, 2023.

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More on Google Bouncing Mail

The complaints with Google bouncing mail coming from Microsoft 365 IP addresses continued this week.

Microsoft released new recommendations to customers in this article: Outbound spam protection
Using Microsoft 365 account to send bulk mail isn't a supported use of the service and is permitted only on a "best-effort" basis, per the Exchange Online Service Description.

For customers who want to send bulk email Microsoft 365 servers, Microsoft has the following recommendations, but it’s better to use a third party sender to send bulk mail, such as SendGrid, Constant Contact, or Amazon SES. (I use SES to send this newsletter.) You can still use a domain address as the From address (remember to configure SPF to include the sending server.)

And use mail merge, not BCC.

• Don't send a large rate or volume of email that causes you to run afoul of the sending limits in the service. This recommendation also includes not sending email to a large list of Bcc recipients.

• Avoid using addresses in your primary email domain (for example, contoso.com) as senders for bulk email. Doing so can affect the delivery of regular email from senders in the domain. Consider using a custom subdomain exclusively for bulk email. For example, use m.contoso.com for marketing email and t.contoso.com for transactional email.

• Configure any custom subdomains with email authentication records in DNS (SPF, DKIM, and DMARC). Many email service providers (for example, Gmail, Yahoo!, and Outlook.com) are configured to reject messages that don't meet email authentication standards.

The above applies to both Outlook.com consumer accounts and Microsoft 365 business accounts, but Outlook.com accounts won’t have the option of using subdomains or updating SPF records. But anyone with Office 2007 and newer software can use mail merge. (Outlook 2007 and 2010 can only connect to Outlook.com using POP or IMAP. Only Outlook.com will allow Outlook desktop to connect using POP or IMAP; Outlook desktop can only connect to Microsoft 365 Work or School account using exchange services. )

Will switching to another email provider help? No. Many email providers and increasing security and trying to stop spam before it gets inside the server.

More information:

Prevent mail to Gmail users from being blocked or sent to spam - Gmail Help (google.com)

Set up SPF to help prevent spoofing

Use DMARC to validate email, setup steps

How to use DKIM for email in your custom domain

New Computer and Importing Old Data

One mistake many users make when they get a new computer is to export mail from the old computer and import it in the new computer.

Import and Export is not necessary. If you have pst files on the old computer, copy them to the new computer and open them in Outlook using File > Open & Export > Open Outlook data file. This will retain the view you use on the folders, categories and other data that does not export.

If you use a POP account, copy the pst before you begin and put it in Documents \ Outlook Files folder. When you add the account to Outlook, you can choose to use an existing pst – select the one you copied.

Mail in IMAP and Exchange accounts (including outlook.com) is stored on the server, so no need to export it from the old computer. As soon as you add the account to Outlook, the mail will sync down (and calendar, contacts, tasks in an Exchange account.)

The one exception: if you use IMAP and have calendar, contacts, and tasks in the IMAP data file, in folders named ‘this computer only’ you need to export the contents and import on the new computer.

Do not import a pst file in an IMAP account. You’ll either have duplicates or a lot of sync issues.

If you imported mail and need to remove the duplicates, add the Modified date field to the view and sort by it. The imported mail will have the date and time of the import. If the messages are in multiple folders, use Search folders to find the messages, with the criteria being modified = the import date.

Rules for spam with no sender address

If you are receiving spam that is not getting filtered into the junk mail folder, you can mark it as junk and add the address to the blocked list. Or you can use rules to delete the messages.

But what if the From address is blank? How can you block an address that doesn't exist?

Easy, you need to check the sender address.

There are two ways you can do this: one rule with an exception or two rules.

1. Create a rule to delete all mail except if the sender address has an @ sign. I recommend testing it first by moving mail to a new folder then after confirming there are no unintended consequences, change it to delete.

If you use other rules, this should be the last rule in the list and all of the previous rules should have Stop processing rules, otherwise you end up with duplicates.

2. If you prefer to use two rules, the first one is if sender address has an @ sign, move to Inbox and Stop Processing rules. The second rule deletes all mail that is not processed by earlier rules.

As with the single rule, if you have other rules the @ sign rule will be next to last and the last rule will delete all mail. The previous rules should have Stop processing rules, otherwise you end up with duplicates.