How to Resolve WordPress HTTP to HTTPS Issues on a Windows Server

If you’ve recently switched your WordPress site from HTTP to HTTPS on a Windows server and are facing challenges, you’re not alone. Transitioning to a secure connection can be tricky, especially when dealing with the web.config file. In this guide, we’ll walk you through a step-by-step solution based on a discussion from fellow users who encountered similar problems.

1. Identify the Problem

The initial post highlights issues with loading CSS/JS files and complications with web.config when switching from HTTP to HTTPS. The user has already added define('FORCE_SSL_ADMIN', true); in the wp-config file, but the problem persists.

2. Consider Linux Migration

One suggestion from the community is to consider migrating the WordPress installation to a Linux server. The user reports that their hosting company plans to convert their WordPress installation to Linux to resolve the issues. If you have the option, this could be a viable solution.

3. Explore a Plugin

Another user recommends a WordPress plugin called Really Simple SSL. This plugin is suggested for those experiencing issues on Linux servers. It simplifies the SSL setup process and could potentially resolve your problems.

4. Modify the web.config File

If you’re committed to using a Windows server, a user provides a code snippet to be added to the web.config file. This code snippet handles HTTP to HTTPS redirects and adds Strict-Transport-Security headers.


<system.webServer>
<rewrite>
<rules>
<rule name="HTTP to HTTPS redirect" stopProcessing="true">
<match url="(.*)" />
<conditions>
<add input="{HTTPS}" pattern="off" ignoreCase="true" />
</conditions>
<action type="Redirect" url="https://{HTTP_HOST}/{R:1}" redirectType="Permanent" />
</rule>
</rules>
<outboundRules>
<rule name="Add Strict-Transport-Security when HTTPS" enabled="true">
<match serverVariable="RESPONSE_Strict_Transport_Security" pattern=".*" />
<conditions>
<add input="{HTTPS}" pattern="on" ignoreCase="true" />
</conditions>
<action type="Rewrite" value="max-age=31536000" />
</rule>
</outboundRules>
</rewrite>
</system.webServer>

Copy and paste this code into your web.config file. It sets up rules for redirecting HTTP to HTTPS and adds security headers.

5. Test and Troubleshoot

After making changes, thoroughly test your website. Check if the CSS/JS files are loading correctly, and ensure that the HTTP to HTTPS redirects are functioning as expected. If issues persist, consider seeking further assistance from your hosting provider or the WordPress community.

By following these steps, you should be on your way to resolving the HTTP to HTTPS transition issues on your WordPress site hosted on a Windows server. Always remember to back up your files before making significant changes and stay vigilant during the testing phase.

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