Troubleshooting Guide: Enable Images in Emails

In Microsoft Outlook, automatic image downloads are often disabled by default for security reasons. This can affect how simulated phishing emails display and may also impact tracking accuracy.

To ensure emails display correctly, you may need to adjust Outlook settings and trust specific simulation domains.

Enable Automatic Image Downloading

Open Trust Center Settings

In Outlook Desktop:

Go to File > Options
Select Trust Centre
Click Trust Centre Settings

Allow Image Downloads

Go to Automatic Download
Untick: “Don’t download pictures automatically in HTML e-mail messages or RSS items”

If available, ensure this is ticked:

✔ Permit downloads from websites in this security zone: Trusted Zone

Note: Menu options may vary slightly depending on your Outlook version (Microsoft 365 vs older desktop versions). Some options may also be managed by your IT administrator.

Add Simulation Domains to Trusted Sites (Windows)

Open Internet Options

Open Internet Options in Windows.
Go to the Security tab.
Select Trusted Sites, then click Sites.

Add Trusted Domains

Add the following domains:

Note: This ensures both simulation emails and training landing pages load correctly without filtering, rewriting, or security inspection by email and web security tools.

Verify Advanced Security Settings

Check Encrypted Page Settings

In the same Internet Options window:

Go to the Advanced tab.
Scroll down to the Security section.
Ensure the following is unchecked: ❌ Do not save encrypted pages to disk
Click Apply, then OK

Note: This is a legacy setting and may not be available or applicable in all environments.

Organisation-Wide Configuration (Recommended)

If your organisation manages Outlook centrally, these settings may be controlled via policy. In that case, changes will need to be made by your IT team using:

Group Policy (GPO)
Microsoft Intune policies for Outlook
Safe Senders / Trusted Domains configuration

Microsoft Resource: Deploy Safe Senders settings using Group Policy in Outlook

Notes:

Changes may require a restart of Outlook to take effect
Some settings may be restricted by your IT administrator
In modern Microsoft 365 environments, certain options may not be visible or may be controlled centrally
These steps are intended for testing and simulation environments only