How to Prevent Outlook from Sending winmail.dat Attachments on iPhone

Have you ever sent an email from Microsoft Outlook, which has a file attachment, to someone using an iPhone or iPad? Do they then call saying that they cannot open the winmail.dat you sent?

This is a common problem. Many people face this issue daily. Your email recipient gets a winmail.dat file rather than your original document. They can’t open it on their iOS device.  If you have any issue related to to iphone guide then visit this page.

Why Does Outlook Send winmail.dat Files to iPhone Users?

Understanding the winmail.dat Problem

Outlook sometimes sends information RTF (Rich Text Format) emails. You can write in bold, color text, and other formats.

Apple devices cannot understand RTF format. This is the problem. Your iPhone or iPad creates winmail.dat file when you get an RTF email. This file contains all the formatting and file attachments.

Here’s what happens:

• You send a PDF or JPEG from Outlook
• Outlook wraps it in RTF format
• The iPhone can’t read RTF
• It shows winmail.dat instead of your original file

Common Scenarios When This Happens

This problem happens most often in these situations:

This regularly happens in corporate environments that utilize Office 365 or Outlook 2019/2021. If you are a Windows user, and you emailed an iPhone user, they received winmail.dat files.

Mixed email client usage also causes problems. People who use Outlook to send email to Apple Mail, Gmail, and Thunderbird users often attach winmail.dat files.

Auto-complete issues can make this worse. Outlook remembers how to send emails to each person. Sometimes it remembers the wrong email format.   If you have any issue related to Top 9 Problems iPhones then dont worry we also provide solution of this issue here on this website.

How to Stop Outlook from Creating winmail.dat Attachments (Sender Solutions)

Method 1 – Change Default Message Format in Outlook

This is the most important fix. The email format needs to be modified from RTF email format to HTML email or plain text email format.

For Windows Outlook users:

1. Open Microsoft Outlook on your computer
2. Click on “File” and then “Options”
3. Select “Mail” from the left menu
4. Look for “Compose messages in this format”
5. Change it from RTF to HTML or Plain Text
6. Find “Message format” section
7. Set “When sending messages in Rich Text format to Internet recipients” to “Convert to HTML“
8. Click “OK” to save

This change affects all future emails. Now, your mail attachments will work perfectly on your iPhone and iPad.

Method 2 – Adjust Individual Contact Settings

Sometimes you need different settings for different people. This method allows you to change settings for your contacts.

Here’s how to do it:

1. Start writing a new email
2. Type the email address in the “To” field
3. Right-click on the email recipient address
4. Choose “Outlook properties” from the menu
5. Find “Internet format” dropdown
6. Select “Let Outlook decide the best sending format“
7. Click “OK”

This fixes the problem for that specific person. If you email a lot of iPhone users, you may have to do this.

Method 3 – Use Plain Text Format for iPhone Recipients

Plain text email is the simplest format. It always works with iPhone and iPad devices. You will lose formatting but your file attachments will work.

To use plain text:

1. When writing an email, click “Format Text” tab
2. Choose “Plain Text” button
3. Outlook will ask if you want to convert to plain text
4. Click “Yes”
5. Send your email

Plain text emails are smaller and faster too. They are compatible with all email clients, including Gmail, Apple Mail and Thunderbird.

Method 4 – Clear Outlook Auto-Complete List

Your Outlook auto-complete list remembers old settings. Sometimes it remembers to send RTF format to iPhone users. Clearing this list can help.

Follow these steps:

1. Go to File > Options > Mail
2. Find “Send messages” section
3. Click “Empty Auto-Complete List“
4. Check the box “Use Auto-Complete List to suggest names”
5. Click “OK”

This gives you a fresh start. Outlook will once again determine the correct email format for everyone.

How iPhone Users Can Open winmail.dat Attachments (Recipient Solutions)

Best iPhone Apps for Opening winmail.dat Files

If you’re an iPhone user receiving winmail.dat files, you can install apps to open them. The App Store has many options.

Top-rated free apps.

Look for “winmail.dat” in the App Store. Look for apps with good ratings and reviews. Most free apps work well but might show ads.

Popular paid apps usually have more features. They are able to better manage Excel sheets, PDF files and JPEG images.

How to use these apps:

1. Download a winmail.dat app from App Store
2. Open the email with winmail.dat file
3. Tap “Share” button
4. Choose your winmail.dat app
5. The app will show your original file attachment

Alternative Methods for iPhone Users

Forward the email to a Gmail account. Gmail often opens winmail.dat files by itself. Then you can download the real file attachment.

To use web-based viewers, save the winmail.dat file, then upload it to the viewer. This works for PDF and JPEG files.

Request the sender to send the email again in HTML or plain text. This is often the best solution.

Troubleshooting Common Issues When Preventing winmail.dat Attachments

Settings Changed But Still Getting winmail.dat Files

This frustration happens to many people. Even after changing all the settings, iPhone users get winmail.dat files.

Common causes.

Your auto-complete list might override your new settings. Try the method above to clear it.

Contact-specific settings might be wrong. Check individual email properties for problem contacts.

Corporate Exchange servers sometimes force RTF format. Ask your IT department about this.

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Mac Outlook Users – Special Considerations

Different versions of Outlook on MacBook Pro and other Macs. The settings are in different places.

For Mac Outlook:

1. Look in Outlook Preferences instead of Options
2. The menus are different from Windows
3. Some features might not be available

The fix is likely limited for Mac Outlook version 16.89 and such. Consider using Gmail or Apple Mail instead.

Office 365 and Outlook Online Solutions

Web-based Outlook settings differ from desktop Outlook. The email format options are in different places.

For Outlook Online:

1. Click Settings gear icon
2. Go to “View all Outlook settings”
3. Select “Compose and reply”
4. Choose HTML as default format
5. Save changes

Usually the default for the mobile Outlook app on iPhone is to send email in HTML. But check the settings to be sure.

Prevention Tips for Different Outlook Versions

Outlook 2019/2021 Desktop Version

Newer Outlook versions have slightly different menus. Steps are the same, but the names of buttons may vary.

Key differences:

The “Message format” settings might be in a different tab. Look for “Email” or “Compose” sections.

Version-specific settings sometimes reset after updates. Check your settings after Microsoft updates.

Outlook 365 Subscription

Cloud-based settings sync across devices. In case you resolve the issues on one computer, it ejects the problems everywhere.

Auto-updates can sometimes change your settings. Make sure that HTML email stays your default every so often.

Your email format should be consistent across your phone and your computer.

Outlook Mobile App

The Outlook app for iPhone normally does not create winmail.dat files. But you should check the settings anyway.

In the mobile app:

1. Open Outlook app on iPhone
2. Tap your profile picture
3. Go to Settings
4. Check “Default format” options
5. Choose HTML if available

Generally, file attachments sent from the app are compatible with other iPhone users.

Advanced Solutions for IT Administrators

Exchange Server Configuration

IT departments can fix this problem for the whole company. Exchange server settings determine the email format for everybody.

Organizational settings prevent winmail.dat for all. It’s better than having to ask each one to change their settings.

You can enforce HTML email format for all your Outlook company users with group policy.

Corporate Environment Best Practices

By training users about proper email formats, issues can be avoided. Show them how to adjust email settings.

Email policies for the company should not use RTF.

It is crucial that the product we choose is compatible with what our employees use; in this case, iPhone, Android, and Windows.

FAQS

What causes some iPhone users to receive regular attachments while others get winmail.dat?

This depends on the set up that outlook has and the email client of the email recipient. Gmail handles winmail.dat better than Apple Mail.

Is it possible to stop winmail.dat without losing message formatting?

Yes. HTML email retains formatting and is compatible with iPhone. Plain text email has no formatting but always works.

Which files does winmail.dat usually cause trouble for?

Most often, users face this issue with pdf, jpeg, excel and word files. Photos and excel sheets frequently turn winmail.dat files.

Is this problem only with the iPhone? Or does the Android device have it too?

The winmail.dat problem can also affect Android devices. But iPhone and iPad users complain about it more often.

Will Microsoft fix this compatibility issue?

Microsoft tweaked the format a bit, but RTF still does not work well.
The best solution is to avoid RTF and use HTML instead.

Alternative Email Solutions to Avoid winmail.dat Problems

Using Gmail or Other Email Providers

In many cases, Gmail handles email attachments better than Outlook. Chrome client access to Gmail seldom creates winmail.dat files.

Moving your contacts and email history is a consideration. But you might avoid attachment problems completely.

Maintaining Outlook integration is possible. Best Email Client allows you to send emails from Gmail and organize emails using Outlook.

File Sharing Alternatives

Cloud storage solutions such as OneDrive, Google Drive and Dropbox are better for big files. iPhone users can always access files from these services.

When to use file sharing:

• Files larger than 10MB
• Multiple file attachments
• When email compatibility is uncertain
• For PDF documents and Excel files

Security considerations include password protecting files and creating expiration dates.

Conclusion

Send yourself an email with an attachment to test your setup. Check if your iPhone or iPad can open it properly.

Email issues with Outlook on Apple devices can be frustrating. But these solutions work for most people.

Share this guide with colleagues who have the same problem. Outlook attachment issues affect millions of people daily.

Setting HTML as your default email format is the best long-term solution. It stops winmail.dat files from forming and keeps emails looking good.

Remember, iPhone users will appreciate your time in fixing this problem. They now don’t receive confusing winmail.dat files in their emails!