An ambulatory infusion pump, comprising: a delivery mechanism adapted to facilitate delivery of insulin to a user; a user interface adapted to display operating parameters of the delivery mechanism and to receive input data from a user; a memory adapted to store a maximum bolus limit defining a maximum bolus amount a user is allowed to enter into the user interface for delivery by the delivery mechanism; and a processor operably connected to the delivery mechanism, user interface and memory, the processor adapted to execute a maximum bolus override procedure when the user manually enters a request for delivery of a bolus amount greater than the maximum bolus amount through the user interface, the maximum bolus override procedure comprising: providing a first alert on the user interface warning the user that the bolus amount in the request exceeds the maximum bolus amount; receiving a first confirmation of the request in response to the first alert; and causing the delivery mechanism to proceed with the requested delivery of the bolus amount that exceeds the maximum bolus amount to the user in response to the first confirmation, including delivering a first portion of the bolus amount, wherein the first portion of the bolus amount is equal to the maximum bolus amount or a predetermined percentage of the maximum bolus amount; after the first portion of the bolus amount is delivered to the user, providing a second alert on the user interface reminding the user that a second portion of the bolus amount comprising a remainder of the bolus amount was requested; receiving a second confirmation to deliver the second portion of the bolus amount; and causing the delivery mechanism to deliver the second portion of the bolus amount to the user in response to the second confirmation. a delivery mechanism adapted to facilitate delivery of insulin to a user; a user interface adapted to display operating parameters of the delivery mechanism and to receive input data from a user; a memory adapted to store a maximum bolus limit defining a maximum bolus amount a user is allowed to enter into the user interface for delivery by the delivery mechanism; and a processor operably connected to the delivery mechanism, user interface and memory, the processor adapted to execute a maximum bolus override procedure when the user manually enters a request for delivery of a bolus amount greater than the maximum bolus amount through the user interface, the maximum bolus override procedure comprising: providing a first alert on the user interface warning the user that the bolus amount in the request exceeds the maximum bolus amount; receiving a first confirmation of the request in response to the first alert; and causing the delivery mechanism to proceed with the requested delivery of the bolus amount that exceeds the maximum bolus amount to the user in response to the first confirmation, including delivering a first portion of the bolus amount, wherein the first portion of the bolus amount is equal to the maximum bolus amount or a predetermined percentage of the maximum bolus amount; after the first portion of the bolus amount is delivered to the user, providing a second alert on the user interface reminding the user that a second portion of the bolus amount comprising a remainder of the bolus amount was requested; receiving a second confirmation to deliver the second portion of the bolus amount; and causing the delivery mechanism to deliver the second portion of the bolus amount to the user in response to the second confirmation. providing a first alert on the user interface warning the user that the bolus amount in the request exceeds the maximum bolus amount; receiving a first confirmation of the request in response to the first alert; and causing the delivery mechanism to proceed with the requested delivery of the bolus amount that exceeds the maximum bolus amount to the user in response to the first confirmation, including delivering a first portion of the bolus amount, wherein the first portion of the bolus amount is equal to the maximum bolus amount or a predetermined percentage of the maximum bolus amount; after the first portion of the bolus amount is delivered to the user, providing a second alert on the user interface reminding the user that a second portion of the bolus amount comprising a remainder of the bolus amount was requested; receiving a second confirmation to deliver the second portion of the bolus amount; and causing the delivery mechanism to deliver the second portion of the bolus amount to the user in response to the second confirmation.