During penetration testing of web applications, different tools are actively used to relieve the tester from repeating monotonous operations. The difficulty of the choice is in the fact that there are tools with similar functionality, and it is hard to define which tool is best to choose for a particular case. In this paper, a solution of the problem with making a choice by creating a Web service that will use a neural network on the server side is proposed. The neural network is trained on

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... obtained from experts in the field of penetration testing. A trained neural network will be able to select tools in accordance with specified requirements. Examples of the operation of a neural network trained on a small sample of data are shown. The effect of the number of neural network learning epochs on the results of work is shown. An example of input data is given, in which the neural network could not select the tool due to insufficient data for training. The advantages of the method shown are the simplicity of implementation (the number of lines of code is used as a metric) and the possibility of using opinions about tools from various experts. The disadvantages include the search for data for training, the need for experimental selection of the parameters of the neural network and the possibility of situations where the neural network will not be able to select tool that meets the specified requirements.