A work assisting server for assisting a remote operation of each of a plurality of work machines using corresponding each of a plurality of remote operating devices, the work assisting server comprising: a database configured to store and hold, in association with one another, an identifier of a remote operating device, an identifier of a linked work machine, which is the work machine linked with the remote operating device, and a real space position of the linked work machine; a first assisting processing element configured to cause one or more work environment images according to one or more picked-up images of a work site acquired through image pickup devices to be outputted on an output interface of each of the plurality of remote operating devices based on communication with the corresponding each of the plurality of remote operating devices; and a second assisting processing element configured to recognize, in a case of receiving a label image request transmitted based on an operation of any one of the plurality of remote operation devices, wherein the label image request is accompanied with the identifier of the linked work machine based on communication with each of the plurality of remote operating devices, the real space position of the linked work machine stored and held in the database in association with the identifier, determine whether or not the real space position of the linked work machine is included in a real space image pickup range of the image pickup device, and, when a result of the determination is positive, cause a label image indicating presence of the linked work machine at a specified position in the work environment image corresponding to the real space position of the linked work machine to be outputted on the output interface of each of the plurality of remote operating devices, wherein the label includes a texture image in which a color can be set by an operator or a mark image in which a symbol can be set by an operator. a database configured to store and hold, in association with one another, an identifier of a remote operating device, an identifier of a linked work machine, which is the work machine linked with the remote operating device, and a real space position of the linked work machine; a first assisting processing element configured to cause one or more work environment images according to one or more picked-up images of a work site acquired through image pickup devices to be outputted on an output interface of each of the plurality of remote operating devices based on communication with the corresponding each of the plurality of remote operating devices; and a second assisting processing element configured to recognize, in a case of receiving a label image request transmitted based on an operation of any one of the plurality of remote operation devices, wherein the label image request is accompanied with the identifier of the linked work machine based on communication with each of the plurality of remote operating devices, the real space position of the linked work machine stored and held in the database in association with the identifier, determine whether or not the real space position of the linked work machine is included in a real space image pickup range of the image pickup device, and, when a result of the determination is positive, cause a label image indicating presence of the linked work machine at a specified position in the work environment image corresponding to the real space position of the linked work machine to be outputted on the output interface of each of the plurality of remote operating devices,