Interrogative structures such as ‘Could you pass the salt? and ‘Couldn’t you pass the salt?’ can be used for making requests. A study of such pairs within a conversation analytic framework suggests that these are not used interchangeably, and that they have different impacts on the interaction. Focusing on Danish interactions between elderly care recipients and their home help assistants, I demonstrate how the care recipient displays different degrees of stance towards whether she is entitled to make a request or not, depending on whether she formats her request as a positive or a negative interrogative. With a positive interrogative request, the care recipient orients to her request as one she is not entitled to make. This is underscored by other features, such as the use of mitigating devices and the choice of verb. When accounting for this type of request, the care recipient ties the request to the specific situation she is in, at the moment in which the request is produced. In turn, the home help assistant orients to the lack of entitlement by resisting the request. With a negative interrogative request, the care recipient, in contrast, orients to her request as one she is entitled to make. This is strengthened by the choice of verb and the lack of mitigating devices. When such requests are accounted for, the requested task is treated as something that should be routinely performed, and hence as something the home help assistant has neglected to do. In turn, the home help assistant orients to the display of entitlement by treating the request as unproblematic, and by complying with it immediately.