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Disclaimer, I am no expert on Grails. But from what you have described, the configuration could be as follows: SSL is offloaded to apache httpd. Hence only the ajp connector needs to be configured in Tomcat, or perhaps with an additional http connector for testing purpose only. Configuring enable SSL for apache httpd by following <a href="http://httpd.apache.org/docs/2.0/ssl/ssl_howto.html" rel="nofollow">http://httpd.apache.org/docs/2.0/ssl/ssl_howto.html</a> and <pre><code><VirtualHost _default_:80> RedirectPermanent /secure/path https://www.example.com/secure/path ProxyPass / ajp://localhost:8009/ ProxyPassreverse / ajp://localhost:8009/ </VirtualHost> <VirtualHost _default_:443> # SSL config ... ProxyPass / ajp://localhost:8009/ ProxyPassreverse / ajp://localhost:8009/ </VirtualHost> </code></pre> should work. Another benefit is that you may see performance improvement when SSL is offloaded to apache httpd. In addition, why not force SSL for everything: <pre><code><VirtualHost _default_:80> RedirectPermanent / https://www.example.com/ </VirtualHost> <VirtualHost _default_:443> # SSL config ... ProxyPass / ajp://localhost:8009/ ProxyPassreverse / ajp://localhost:8009/ </VirtualHost> </code></pre> As to why you have infinite loop, it might be related to Spring Security's sendRedirect. If you can post your full apache VirtualHost and tomcat ajp connector configuration, it may give us more clue.
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1. POGrails + Tomcat + Apache error when switching to HTTPS
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1. POGrails + Tomcat + Apache error when switching to HTTPS
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