Software & Apps MS Office How to Prevent Winmail.dat Attachments from Being Sent in Outlook How to avoid that annoying Winmail.dat attachment by Heinz Tschabitscher Writer A former freelance contributor who has reviewed hundreds of email programs and services since 1997. our editorial process Heinz Tschabitscher Updated on November 09, 2019 reviewed by Ryan Perian Lifewire Tech Review Board Member Ryan Perian is a certified IT specialist who holds numerous IT certifications and has 12+ years' experience working in the IT industry support and management positions. our review board Article reviewed on Feb 20, 2020 Ryan Perian MS Office Outlook Word Excel Powerpoint Tweet Share Email Do recipients of your emails complain about a mysterious attachment called winmail.dat which they cannot open? Do files you attach to emails disappear in that winmail.dat abyss? Does winmail.dat show up for some but not all recipients of your messages? Fortunately, you can get rid of winmail.dat altogether by making sure Outlook does not send mail using RTF. Instructions in this article apply to Outlook 2019, 2016, 2013, 2010, 2007, 2003; and Outlook for Microsoft 365. When, How, and Why Winmail.dat is Created Lifewire If Outlook sends a message using the RTF format for bold text and other text enhancements, it includes the formatting commands in a winmail.dat file. Receiving email clients that do not understand this code display it as an attachment. Outlook may also pack other file attachments in the winmail.dat file. Prevent Winmail.dat Attachments from Being Sent in Outlook To prevent Outlook from attaching a winmail.dat file when you send an email: Go to File. Select Options. Go to Mail. In the Compose messages section, select the Compose messages in this format dropdown arrow and choose either HTML or Plain Text. In the Message format section, select the When sending messages in Rich Text format to Internet recipients dropdown arrow and choose either Convert to HTML format or Convert to Plain Text format. Select OK. Prevent Winmail.dat Attachments in Outlook 2007 and Outlook 2003 To make sure Outlook 2007 to Outlook 2003 do not attach winmail.dat files: Select Tools > Options. Go to Mail Format. Under Compose in this message format, choose either HTML or Plain Text. Click OK. Disable Winmail.dat for Particular Recipients The standard settings for outgoing mail formats in Outlook can be overridden for an individual email address. If a recipient still receives a winmail.dat attachment after you have made the settings changes, reset the format for individual addresses. In Outlook 2019 and 2016 Make sure the email address is not in your Outlook Contacts. Outlook 2019 and 2016 currently offer no way to change sending preferences for email addresses that are assigned to an address book entry. Open an email from the desired email address or start a new message to it. Right-click the address. Select Open Outlook Properties. Under Internet format, select Send Plain text only. Select OK. In Outlook 2013, 2010, and 2007 Search for the desired contact in your Outlook Contacts. Double-click the contact's email address or right-click the desired email address, then select either Open Outlook Properties or Outlook Properties. Under Internet format, select either Let Outlook decide the best sending format or Send Plain Text only. Click OK. Extract Files from Winmail.dat without Outlook If you receive winmail.dat attachments with embedded files, extract them using a winmail.dat decoder on Windows or OS X.