Dear @Kurt Clancy,
I understand how frustrating it is when photos you send from your iPhone no longer appear in Outlook, especially when this was working before. To help us better understand what’s happening, could you please confirm the following:
- Do the emails themselves arrive in Outlook, or are they missing completely when you send photos from your iPhone?
- When you open the sent message on your iPhone, do you see the photos attached, or are they shown as links (for example, iCloud links)?
- Which app is you using on the iPhone to send the photos? (Outlook for iOS or Apple Mail)
- Does this happen only when sending photos to yourself, or also when sending photos to other recipients?
- Could you let me know which email account you’re using in New Outlook for Windows (work/school vs personal), and whether the same account is used on your iPhone?
- Is your iPhone managed by your organization (company policies, Intune, device management)?
- Does this issue also happen when you use other devices or other accounts to send the photos?
- Could you please share a screenshot of the issue (for example, how the email appears in Outlook where the photos are missing)? (Note: Please remember to cover or remove any personal or sensitive information (email addresses, names, or account details) before sharing the screenshot).
In most cases, this behavior is related to how images are handled or blocked for security reasons rather than a delivery failure. Please check the following:
Step 1: Confirm the email is arriving
In Outlook (New Outlook for Windows), please check your Inbox, Junk Email, and Deleted Items folders. Also review any inbox rules or Focused Inbox settings to ensure the message is not being moved automatically.
Step 2: Check image settings on your iPhone
If you use Outlook on iPhone, go to Settings > search for "Block external images" and make sure this is turned off.
Step 3: If you use Apple Mail on iPhone
Please open the Sent folder on your iPhone and confirm the photos are actually attached. Sometimes photos are sent as iCloud links instead of full attachments, which Outlook may block as external content.
Step 4: Work or managed device
If this is a work account or a managed device, mobile security or app protection policies may block photos from being shared into Outlook. In this case, your IT administrator will need to review the settings.
Note: Please understand that as a forum moderator, my role is to provide general guidance and troubleshooting support. I don’t have access to internal systems or backend tools, and I appreciate your understanding of these limits.
I hope the information shared helps point you in the right direction. Please try the steps above and let me know if they work. If not, we can continue working together to narrow this down.
The first response may not always resolve the issue right away, but with your help and more details, we can work toward a solution.
Thank you for your patience and understanding. I'm looking forward for your reply.
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