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https://live.paloaltonetworks.com/t5/Management-Articles/GlobalProtect-Requests-System-Keychain-Access-on-Mac-OS-X/ta-p/53332 Issue Machine Certificate authentication is used on MAC OS X clients. During the GlobalProtect connection process, the user needs to enter the Local Administrator account credentials to allow access to the System keychain twice.   Cause When using Machine Certificates with GlobalProtect on Mac OS X Clients, the certificate must be accessed from the "System" keychain in MAC OS X.  This will cause a Keychain Access prompt to appear twice when the client attempts to access the certificate for verification against both portal and gateway. Workaround     Open the Keychain Access application and locate the Machine Certificate issued to Mac OS X Client in the System keychain.     Right-click on the private key associated with Certificate and click Get Info, then go to the Access Control tab     Click '+' to select an Application to allow     Press key combination <Command> + <Shift> + G to open Go to Folder     Enter '/Applications/GlobalProtect.app/Contents/Resources' and click Go     Find PanGPS and click it, and then press Add     Save Changes to private key   PS: our MAC begin connecting only after all apps access were given to the key file. The steps above allows GlobalProtect access to only THIS certificate and private key.  It will no longer prompt for keychain access, giving users a seamless, no-touch experience with Palo Alto Networks GlobalProtect. Note: The procedure has to be done again every time client is updated.   https://live.paloaltonetworks.com/t5/Configuration-Articles/macOS-X-10-13-amp-iOS-11-New-Requirements-for-GlobalProtect/ta-p/179049 ... View more

Thanks for looking at my query. OS: Windows 7 Enterprise 64-bit. Several other clients are able to connect running same OS and client version so I'm not sure what's up with this particular client. ... View more