Attachment Issues

How to Stop Outlook Emails from Going to Spam and Fix JPEG Insert Issues

Maira Mehtab Sep 22, 2026 869 views

Question details

The user's Outlook account is incorrectly marking emails from microsoft.com addresses as spam, and they are experiencing difficulties inserting JPEG image attachments into their emails.

Product: Microsoft Outlook
Device & OS: not provided
Scenario: Receiving legitimate emails from Microsoft and trying to attach JPEG images to outgoing messages.
Observed behavior: Emails from microsoft.com are automatically sent to the Junk Email folder, and JPEG images cannot be inserted into messages.

Before you start

Before adjusting your spam settings, always verify the email headers and embedded links to ensure the message is genuinely from Microsoft and not a spoofed phishing attempt.

Solution 1Recommended

Verify Authenticity and Move to Inbox

Confirm the email is safe and add the sender to your safe list to prevent future emails from going to spam.

Because sender addresses can be spoofed, an address ending in microsoft.com does not automatically guarantee safety. Once you confirm its legitimacy, you can train your mailbox to trust it.

Verify email authenticity

Check the message headers and hover over any links in the email to ensure they direct to legitimate Microsoft domains before taking action.

Move to Inbox

Right-click the legitimate email in your Junk Email folder, hover over 'Junk', and select 'Not Junk' to move it to your Inbox.

Trust the sender

When prompted during the move, check the option to always trust emails from this sender address, effectively adding them to your Safe Senders list.

Tip: Adding the entire domain (@microsoft.com) to your Safe Senders list in Junk Email Options can help prevent related legitimate emails from being marked as spam in the future.

Solution 2

Check Mail-Flow Rules (Microsoft 365 Business)

If you are using a corporate account, organization-wide rules might be overriding your personal settings.

Solution 3

Troubleshoot JPEG Attachment Restrictions

Resolve issues preventing you from inserting JPEG images into your Outlook emails.

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Frequently Asked Questions

Why are legitimate Microsoft emails going to my Junk folder?

Outlook's spam filters evaluate multiple factors. Even if the sender address ends in microsoft.com, suspicious headers, bulk sending patterns, or strict organizational mail-flow rules set by your IT administrator can trigger the junk filter.

Can an email showing a microsoft.com sender address still be a scam?

Yes, malicious actors can spoof sender addresses to make it appear as though an email is from Microsoft. Always verify the actual email headers and hover over embedded links before clicking anything or trusting the sender.

How do I whitelist an entire domain in Outlook?

Go to your Junk Email Options, click on the 'Safe Senders' tab, click 'Add', and type the domain (e.g., '@microsoft.com'). This ensures future emails from this domain bypass the junk filter.

Why won't Outlook let me attach a JPEG file?

This usually happens due to exceeding the maximum attachment size limit, strict browser security settings if you are using Outlook on the web, or a temporary application glitch. Try reducing the image file size or using a different browser.

Outlook & Email Problems