As in block 502, a connection request received from an origin endpoint associated with a customer account to initiate a connection with a destination endpoint over a network may be received at the communication service described in relation to FIG. 1. In response to receiving the connection request, the communication service may identify a customer account associated with the connection request, as in block 504, and make a determination whether the destination endpoint is categorized as a high risk destination endpoint, as in block 506. For example, a risk score can be calculated for the destination endpoint, and if the risk score exceeds a threshold, then the destination endpoint can be identified as a high risk destination endpoint. In the event that the destination endpoint is identified as a high risk destination endpoint, then the communication service may determine whether the customer account is linked to a condition that a trust score for the customer account be evaluated prior to allowing the connection to the high risk destination endpoint, as in block 508. If the customer account is not linked to the condition that a trust score be evaluated, then as in block 516, the communication service may initiate the connection with the destination endpoint. However, if the customer account is linked to the condition, then as in block 510, the communication service may obtain a trust score indicating whether the connection request should be allowed, as described earlier.