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How can I add a second or 3rd custom url under on site (https://mysite.secure.salesforce.com/pageone and https://mysite.secure.salesforce.com/pagetwo) When clicking the button to add a custom url I don't have an option to choose the mysite.secure.salesforce.com domain.

I'm trying to avoid adding multiple sites just to have /pageone and /pagetwo

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Custom URLs is a bit of a misnomer - it determines the root URL (incl. path) for the site but you can only have one of those.

There are 2 options to implement this:

  1. Add a page (Visualforce or Lightning) and associate with a Site. The Name of the page determines the resulting URL. For example, if the Name of your page is pageone, then https://mysite.secure.salesforce.com/pageone will spring into existence without you having to explicitly define it under a Site.

  2. Add a URL redirect. via Site > URL Redirects button. This is a good option if you have a bunch of pages with longer, user-unfriendly names and you want to 'alias' them to shorter, more vanity-like URIs. It also helps some with search engines. Example: https://mysite.secure.salesforce.com/login can redirect to https://mysite.secure.salesforce.com/some/path/SiteLoginPage

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