Finding problems with email headers in Outlook

It's easy to find the header for an email message in Outlook. Follow these steps. (I'm working with Outlook 2016 in this example).

1. With a message open go to File . . . Properties

2. In the Properties dialog box the message's header information will be listed at the bottom.

An email header may make reference to an IP address. A forged email may use an IP address that does not match up with domain listed in the sender's email address. If you get an email from jsmith@edrm.net which the header indicates came from the IP address 64.207.183.193, you can confirm that the sender is from the edrm.net by checking its IP address with the tracert command in Windows. The IP address is the number listed at the end of the line beginning, 'Tracing route to . . .'

It's also a sign that an email has been forged if it's purports to be from a particular email client but its Mail User Agent format varies from the official pattern.

A list of common MUA header formats can be found here.

Importing .eml files into Outlook

If you have the 32 bit version of Outlook, there's a simple way to import .eml files. Dragging and dropping them into a folder should successfully import the files with the metadata saved intact (the email addresses from the recipient field in the .emil file should be shown in the 'To' field in Outlook and so on.)

If this is not successful you can try importing the .eml files into Windows Live Mail, and exporting them to a .pst archive file from there.

If you are running the 64 bit version of Outlook neither of these techniques will work. You will be able to drag and drop .eml files into an Outlook folder, but the metadata will not be imported correctly. Instead of the correct author name, you will get the name of your Outlook profile; instead of the correct date sent, you'll get the current date and time.

Mail Passport Lite provides a solution to this problem. This application will import multiple .eml files and save them together in a single .pst archive file.

Open Mail Passport by clicking on the shortcut saved to your desktop. Simply browse to the folder containing the .eml files you need to process. You'll be prompted to select a location to save the new .pst file to.

When the .pst archive is opened in Outlook the metadata information will be displayed correctly.

The trial version of this application will only process 10 .eml files at a time. A license costs $99. Mail Passport can also process mbox archive files (used by Eudora and Mozilla's Thunderbird email application.

The Trouble with Outlook Email Encryption

You can send encrypted messages using MS Outlook, but there may be a problem.

In a message if you click on the option for More Options at the bottom right of the tool bar:

. .. a Properties dialog will open with a Security section. Clicking on Security Settings will bring up the option to encrypt the body and attachments to an email.

Click on "Change Settings . . ." and you'll see that you have the option to set a cryptography format. The default format is S/MIME.

Secure/Multipurpose Internet Mail Extensions is a standard public key encryption, but it has been compromised.

The Electronic Frontier Foundation posted a notice last month, stating that a flaw may allow the plaintext of emails encrypted with PGP and S/MIME to be revealed. Security experts are recommending that that it these encryption methods be disabled from email clients.