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I am publishing data to ArcGIS Online through ArcGIS Server as live feature services. We are using the http server URL but our ArcGIS Online organization is an https URL. Every time I want to display my data I have to push the button to "Show all content" to display secured content at the bottom of the map viewer.

Do I need to change my server to the https URL or is there possibly another system configuration that could be causing this error?

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Yes you will want to change your server to support https. Here is a link to the doc to help you out. http://server.arcgis.com/en/server/latest/administer/windows/enable-ssl-on-arcgis-server.htm

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