Email attachments disappear when sent to others

Whenever I send an attachment through Outlook, the recipient receives the email without the attachment.

It happens to all attachments regardless of who I send it to and the format of the file (eg PDF, Word, jpg, etc). If send the same attachment through web mail or from another computer, the attachment remains intact and is received in the email.

I’ve tried turning off my anti-virus program but that’s not made any difference, so I’m assuming the issue must be within Outlook itself.

This happens when you are sending in RTF-format and the message doesn’t get properly converted. The best thing is to never compose your messages in RTF-format as you can only really rely on this format when you are in an internal Exchange environment with only Outlook clients but that is a whole different technical story of its own.

General options
To verify that you are not sending in Rich Text in general go to;
Tools-> Options…-> tab Mail Format

Contact specific options
It can also be that that particular contact is set to “Send using Outlook Rich Text Format”. To verify;

1. Open that specific contact by double clicking the item in your Contacts folder
2. Double click on the email address of the contact and a dialog will open called “E-mail Properties”
3. Make sure that the “Internet format” is set to “Let Outlook decide the best sending format”.

Internet Format options
In addition, make sure that Outlook is set to convert Rich Text formatted emails to convert to the HTML or Plain Text message format when sending a RTF-message to the Internet;
Tools->Options-> tab Mail Format-> button Internet Format…

Changing the E-mail properties for the contact’s address.