How to solve problems with attachments in Outlook in Windows 10

Arif Bacchus

Updated on:

recall an email in outlook

Inserting attachments is a key part of emailing in Outlook. But, sometimes, not everything might go as planned. You might not be able to attach a file to Outlook at all, or attachments might not show up in the body of emails, or as you intended. In this guide, we’ll help you solve some common problems with attachments in Outlook, and help stop the fretting.

Outlook says that files my are unsafe, or that the file is too big

One of the most common problems with attachments in Outlook is that it might block file types that it thinks are unsafe. Or, the file size might be too big. This is because Outlook blocks certain file types that it thinks might spread computer viruses. And, also because Outlook has a size limit for files. You can work your way around this by zipping the file and then attaching it. Here’s how.

  1. Head to where the file you want to attach is located
  2. Right-click on the file and choose to Send to compressed (zipped) folder
  3. Head back into Outlook and attach and send the new zipped folder instead

Some file types that are blocked by Outlook include .ade, .adp, .app. .bat, .com, .jar, .inf, and .ops. The full list is available here. If you’re unable to zip, or if the file type is still too big, you can always upload the file to the cloud, and then share the link instead.

Sending a file to a zipped folder

My attachments show up in the message body and not below the subject line

If your attachments are showing up in the body of a message and not below the subject line, then, the issue is because of the file type of the email you’re sending. If you’re replying to or using the Rich Text format for your email, all attachments will show up in the body of the message. Here’s how you can switch the format of all outbound emails back to HTML or Plaintext.

  1. Head to the File tab on Outlook
  2. Choose Options and then click Mail
  3. Under Compose Messages look for the Compose messages in this format option
  4. Choose HTML or Plain Text
Switching emails to HTML format

When composing your email, you can look out for what format the email is by looking at the title bar of Outlook. You’ll typically see the subject of the message, along with (Rich Text) or (HTML.) Keep an eye out, to avoid having errors with attachments

I can’t insert Pictures into my email and switching individual emails into HTML or Rich Text formats

Finally, if you can’t insert pictures using the Insert tab in the Outlook ribbon, then again, you’re probably using the wrong format of email. You only can insert pictures info emails when using the HTML or Rich Text formats. Follow the steps above to switch the email format, or you can follow the steps below to switch an individual message into HTML or Rich Text formats.

  1. Click Reply, Reply All, or Forward in the message
  2. If you’re working from the Reading Pane, click Pop Out
  3. Click the Format Text ribbon on the top
  4. Choose HTML or Rich Text under where it says Format
Resolving the issue where you can’t send pictures with the insert button

Did these solve your problems?

Did these solutions to common problems with Outlook attachments solve your problems? If so, feel free to let us know in the comments below. Also, feel free to check out our other Outlook themed guides. We’ve explained our tips and tricks for attaching files in Outlook, and have detailed how you can set up and manage your email accounts in Outlook in Office 365.