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Ultimate Guide on How to Attach a File in Outlook with Ease

  • By Steven
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  • Updated on July 28, 2025
Introduction:
Outlook is a Microsoft information management platform that enables you to manage your email, files, and calendars securely. Outlook is compatible with several email services, including Gmail, Microsoft 365, Yahoo, iCloud, IMAP, and POP. How can you add attachments in Outlook on different devices? In this SwifDoo PDF post, I’ll present you with an ultimate guide on how to attach a file in Outlook. Now, let’s delve into this tutorial post!
summary

About Attachment Size Limits on Outlook

Before getting to learn how to attach files in Outlook, it’s essential to know what the maximum file size for Outlook attachments is. For Outlook.com and Gmail in the Outlook desktop client, the maximum attachment size is 20 MB. For Exchange, the default maximum attachment size is 10 MB. How to send large files via email? You can compress them before sending or send them via cloud services.

If you want to send a PDF to email and its file size exceeds the 10 MB maximum limit, you can use SwifDoo PDF to complete the PDF compression task.

How to Attach a File in Outlook Desktop

Microsoft Outlook can work on both Windows and Mac computers. In this section, I’ll show you the exact steps to attach a file to an email message in Outlook.

Tips: For Windows users, you should clarify which Outlook version you are using. If there is a File option on the ribbon, you are using classic Outlook. If there isn’t, you are using New Outlook.

Step 1. You can open a new email or reply to an email. For new Outlook, you can select the Attach file option from the Insert tab. Here, you can choose to attach a file from your computer, cloud service, or by pasting a link. For classic Outlook, you can go to the Message tab and select the Attach File option from the Include menu. Next, choose where you want to add the attachment from.

Click the Attach file option under the Insert tab for New Outlook

Step 2. Click the Insert button, and then the file will appear in the email.

Tips: If you need to add multiple files in Outlook, you can press the Ctrl key or Command key to choose the target files and click the Insert button.

Alternatively, you can open the target file in File Explorer or Finder and directly drag and drop the file into Outlook to add this file attachment.

Directly drag and drop the target file into Outlook

Steps to Attach a File in Outlook Web and Mobile

In addition to offering desktop versions, Outlook also has a web version and provides mobile applications for iPhone and Android. How to add attachments in Outlook web and mobile? Please read on!

#For Outlook Web

You can opt to attach a file in Outlook on the web or Outlook.com. What you need to do is sign in with your Outlook account first. Then, you can start a new email or reply/forward an email. Under the Insert tab, you can open the Attach file list and choose from Browse this computer, OneDrive, Upload and share, and Link. Next, select the target file and click Open to add the attachment file.

Click the Insert tab and choose one options from the Attach file list in the Outlook web version

#For Outlook Android/iPhone

Step 1. Download Outlook from the App Store or the Google Play Store and install it on your Android or iPhone.

Step 2. Run the Outlook app and sign in with your Outlook account. Next, you can start a new email or reply to an email.

Step 3. Tap the Paperclip icon and select the Attach File option from the list. Next, you can locate a file from the target source, select the target file, and insert it.

Tap the Paperclip icon and select the Attach File option to load your target file into the Outlook app on your phone

Fix “Fail to Add Files in Outlook”

It can be frustrating when you fail to add files or other attachments in Outlook. How come? What solutions can you pick to troubleshoot that error? Don’t worry! I’ve summarized several possible causes and feasible solutions. Follow me to get the answers now!

#Potential Causes

  • Exceed Outlook's maximum file size limit.
  • The file is recognized as unsafe.
  • Certain compatibility and profile issues.
  • Overly strict antivirus software or firewall rules.

#3 Workable Solutions

Fix 1. Compress the attached file.

If the file is too large, you need to use a file compressor to shrink its file size. Alternatively, you can upload the large file to a cloud service (like OneDrive) and share the attached file as a link. The PDF files may not attach to an email in Outlook if they exceed the maximum size supported by Outlook. In that case, you need to compress PDF files to reduce file sizes. SwifDoo PDF can finish the PDF compression task efficiently.

Fix 2. Send the file via the “Send to” option.

If there are some block-type rules, you can choose to send the file as a compressed folder. You need to locate the file and right-click it. Move to the “Send to” option and select the Compressed (zipped) folder option. Then, a .zip file will be created. You can attach the ZIP file in Outlook.

Right-click on the target file and choose the Compressed (zipped) folder option from the Send to list

Fix 3. Try the web version of Outlook.

If you fail to add a file in the Outlook app, you can try to use the Outlook web version to send the same attachment.

In addition to the above solutions, you can try restarting and updating the Outlook app, reviewing antivirus and firewall settings, running Outlook in safe mode, or repairing your Office installation.

To Sum Up

Outlook offers applications for Windows, Mac, iPhone, and Android devices. Also, you can access Outlook on a web browser. Outlook enables you to send emails with attached files. How to attach a file in Outlook? You need to respect its maximum file size limits and other requirements for smooth email sending. In the content above, I show you a detailed tutorial. If you fail to add attachments in Outlook, you need to check the file size and try the other solutions mentioned above. I hope this tutorial will be helpful to you.

Steven is a dedicated contributor at Swifdoo.com. He possesses a deep understanding of various technology domains, including PDF software, program components, and video recording software technologies. He is committed to providing you with the latest insights and solutions to technology-related issues.

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