I have a https SharePoint 2016 on premise site collection. Below are the functionalities implemented in the site collection. 1. SharePoint hosted apps are deployed. for example- SharePoint domain is contoso.com and the app domain is contosoapps.com 2. Because of continous app authenication, i have created a seperate site collection in the name of app domain (https://contosoapps.com) and added https://*.contosoapps.com in the local intranet zone. 3. Two wildcard certificates (.contoso.com and .contosoapps.com) were purchased and they being used for site collection and for other site collection created in the name of app domain.

Scenario 1: When site is browsed from servers in domain, the site collection works fine and SharePoint hosted app works without any authentication prompt in all browsers like IE, Chrome, Firefox and Safari.

Scenario 2: When vpn is connected to the domain from Mac and site is browsed, SharePoint hosted apps are asking for credentials (credential prompt for each and every app in the page) in all browsers.

Can anyone help/advice me on this issue

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