I've found a solution, I guess writing everything down helped to point me in the right direction. If anyone ever has the same problem, here's what I had to adjust.   Disable the captive portal detection in your VPN profile XML if you don't need it (Preferences Part 1 in the Profile Editor): <DisableCaptivePortalDetection UserControllable="true">true</DisableCaptivePortalDetection>  The AutomaticVPNPolicy in the XML shouldn't prompt the user at any point (Preferences Part 2 in the Profile Editor): <AutomaticVPNPolicy>true <TrustedDNSDomains>corp.customer.com</TrustedDNSDomains> <TrustedNetworkPolicy>Disconnect</TrustedNetworkPolicy> <UntrustedNetworkPolicy>DoNothing</UntrustedNetworkPolicy> <AlwaysOn>false </AlwaysOn> </AutomaticVPNPolicy> Be sure to disable all AnyConnect notifications on Windows and in the AnyConnect Client itself, we deploy a .ps1 script to change the settings. # Define the path and property $registryPath = "HKCU:\Software\Cisco\Cisco Secure Client" $propertyName = "EnableStatusPopups" $propertyValue = 0 $propertyType = "DWORD" # Check if the path exists if (-not (Test-Path $registryPath)) { # Create the path New-Item -Path $registryPath -Force } # Create or update the property New-ItemProperty -Path $registryPath -Name $propertyName -Value $propertyValue -PropertyType $propertyType -Force # Define the path and property $registryPath = "HKCU:\Software\Microsoft\Windows\CurrentVersion\Notifications\Settings\Cisco.SecureClient" $propertyName = "Enabled" $propertyValue = 0 $propertyType = "DWORD" # Check if the path exists if (-not (Test-Path $registryPath)) { # Create the path New-Item -Path $registryPath -Force } # Create or update the property New-ItemProperty -Path $registryPath -Name $propertyName -Value $propertyValue -PropertyType $propertyType -Force   Frustrating to deal with this for a paid enterprise software, but I guess we all have to. I couldn't find a solution in any forum, hopefully this will help someone else. ... View more