Can not load or send Pictures with Outlook.com

Use these checks and workarounds in Outlook.com when pictures or photo attachments cannot be added or sent:

1. Check attachment size limits

• Outlook.com has a 25 MB limit per email, including text and all attachments.
• Resizing an image does not reduce its file size; compress the image/file instead or attach it as a OneDrive link.
• For large files, upload to OneDrive and share as a link:
  1. Create a new email (or Reply/Forward).
  2. Select Attach.
  3. If the file is already in OneDrive, choose OneDrive; otherwise choose Upload and share.
  4. Select the file and then Share link.

2. Use OneDrive links if messages with attachments are blocked

• There is a known issue where some Outlook.com users cannot send emails that contain attachments and may see error 550 5.7.520 (Message blocked).
• Until this is fixed, send photos as OneDrive links instead of traditional attachments using the steps above.
• You can also use Copy link from an Office or OneDrive file and paste that link into the email body.

3. When replying to messages with attachments

• If replying to a message that already has photo attachments, those attachments are not automatically included in the reply.
• Use Forward instead of Reply if the original attachments must be kept, or reattach the pictures manually.

4. Calendar events

• Files can only be attached to calendar events that were created by the mailbox owner or a delegate. If trying to attach pictures to an event not created by that account, attachments will not be allowed.

5. If attachments add but the email will not send

• If photos can be attached but the message will not send, follow the Outlook.com email sync troubleshooting steps referenced in the article (for example, from the “fix Outlook.com email sync issues” link).

6. If the problem persists

• Use the built-in Outlook.com help: select Help on the menu bar, enter the issue (for example, “cannot attach pictures”), and if self-help does not resolve it, scroll to Still need help? and choose Yes to contact support.

References:

• Fixes or workarounds for recent issues on Outlook.com
• Unable to attach files in Outlook.com
• Outgoing emails with attachments undelivered as spam - Microsoft Q&A