Sending, receiving, and organizing email in Outlook on the web for business
Hi Christy04,
Thank you for sharing the details of your situation and the screenshots.
To help narrow down the cause, here are some steps you can try:
- Sign out of Outlook on the web, open an InPrivate or Incognito browser window, sign in again, and test the image attachment.
- Try using another supported browser, such as Microsoft Edge or Google Chrome.
- Temporarily disable any browser extensions, particularly ad blockers, privacy extensions, or download managers, by going to your browser menu > Extensions > Manage extensions and turning off the relevant extensions. Then restart the browser and test Outlook on the web again.
- Test with a newly created, small JPG or PNG image saved locally on your device. Please use a simple file name, such as test.jpg.
- Create a new email rather than replying to or forwarding an existing message, then attach the test image and send it to yourself or a colleague.
- Open the test message from your Sent Items folder and check whether the image is still attached and whether you can preview or download it.
- If available, test the same image using the Outlook desktop application or Outlook mobile app. This can help determine whether the issue is limited to Outlook on the web.
As a temporary workaround, you may upload the image to OneDrive and send the recipient a sharing link.
If the issue persists across different browsers, devices, or Outlook applications, please reach out to your organization’s IT administrator for further investigation. The administrator can check message trace, quarantine, mail flow rules, and security policies that may be affecting image attachments.
When contacting your IT administrator, please provide the exact download error message, the image format and file size, the approximate time the affected email was sent, and the results of the troubleshooting steps above.
- For your IT admin reference: Message trace in the new EAC in Exchange Online | Microsoft Learn
- In case you do not know who is your IT admin, kindly refer to this article: How do I find my Microsoft 365 admin? - Microsoft Support
I hope this information is helpful. Should you have any further questions or need additional assistance, please feel free to share them in the comment below. I'm very happy to help.
If the answer is helpful, please click 'Yes' and kindly upvote it.
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