Top 7 Ways to Fix Outlook for Mac Not Sending Attachments

Although the default Mail app has improved with the latest macOS Ventura update, most users prefer Microsoft Outlook to handle emails. Microsoft has done a solid job with a native Outlook app on Mac. But it’s not perfect. Sometimes, Outlook fails to send attachments with an email. If you frequently face the same, here are the ways to fix Outlook not sending attachments on Mac.

You can always move to Outlook for the web to complete the job. But nothing beats a native Outlook experience on Mac. Instead of settling with a below-average web client, use troubleshooting tricks to send emails with attachments.

1. Check Network Connection

If your Mac is facing network issues, Outlook won’t send attachments. You should ensure a robust Wi-Fi connection on your Mac. Click Control Center at the top and enable Wi-Fi on your Mac. You should connect to a 5GHz Wi-Fi network and send attachments on Outlook.

2. Force Restart Outlook

Before we move to advanced tricks to fix the problem, you should force restart Outlook and try sending the attachment again.

Step 1: Press the Command + Space keys and search for Activity Monitor. Hit Return to open the app.

Step 2: Select Microsoft Outlook from the list. Click ‘x’ mark at the top to close the app.

Open Outlook again and send attachments without any problem. If the issue persists, move to other troubleshooting tricks.

3. Check the Attachment Size

Outlook and Gmail email providers limit attachment size to 25 MB only. If you try to send a large file over Outlook, you will continue to face errors. Here’s how you can check file size on Mac.

Step 1: Open Finder on Mac.

Step 2: Find and right-click on a file you want to send over Outlook.

Step 3: Select Get Info from the context menu.

Step 4: Check file size under the General menu.

If the media file size is indeed larger than 25 MB, you should compress it using the Mac Preview. Follow the steps below.

Step 1: Launch Finder and open the video or image using the default Preview menu.

Step 2: Select File at the top and click Export.

Step 3: Use the Quality slider to compress the picture or video.

Step 4: Make sure to reduce file size below 25 MB and click Save.

Launch Outlook and try sending the attachment over email again.

4. Double Check Email Address

You should double-check the typed email address in Outlook for Mac. A small typo in the email address can lead to Outlook not sending attachments issue. You can’t even send a normal email due to an incorrect recipient address.

5. Revert to Outlook Legacy

Many have reported Outlook for Mac not sending attachments issue on the new Outlook app. Microsoft offers an option to revert to the stable legacy version on Mac. Here’s how.

Step 1: Launch Outlook on Mac.

Step 2: Select Help in the menu bar.

Step 3: Click Revert to Legacy Outlook.

The system will restart Outlook and change it to the legacy version. You can now send attachments without any problem.

6. Update Outlook

Microsoft frequently releases Outlook updates on Mac with new features and bug fixes. If you still face issues with sending attachments, update Outlook to the latest version from the Mac App Store.

Step 1: Open App Store on your Mac.

Step 2: Select Updates from the left sidebar.

Step 3: Download and install pending Outlook updates.

7. Try Outlook Alternatives

A buggy Microsoft Outlook build may leave you with a bad user experience. Thankfully, the Mac ecosystem is packed with capable third-party email apps to choose from. One such app is Spark email. You can also go with the default Mail app on Mac.

The default Mail app received a nice feature boost with the macOS Ventura update. You can now undo send, schedule emails, and even use advanced search to find important emails in no time. If you have installed the latest macOS Ventura update on Mac, give it a try.

Enjoy Smooth Communication in Outlook

Outlook for Mac not sending attachments can break your workflow. Before the issue creates miscommunication among team members, use the tricks above to fix the problem.

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