Entry delay / alarm only starts sometimes when entering front door

Hi @pevsfreedom. When this happens, what Mode was your Ring Alarms system set to? The Entry Delay will only trigger after a Main Door is opened if your system is armed in Home or Away Mode, and the Contact Sensor being opened is monitored in that Mode. I’d suggest checking your Modes settings to ensure the Contact Sensor in question is set to be monitored in the Mode you have your system armed in.