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The proliferation of malware in today’s society continues to impact industry, government, and academic organizations. The Dark Web provides cyber criminals with a venue to exchange and store malicious code and malware. Hence, this research develops a crawler to harvest source code, scripts, and executable files that are freely available on the Dark Web to investigate the proliferation of malware. Harvested executable files are analyzed with publicly accessible malware analysis tool services, including VirusTotal, Hybrid Analysis, and MetaDefender Cloud. The crawler crawls over 15 million web pages and collects over 20 thousand files consisting of code, scripts, and executable files. Analysis of the data examines the distribution of files collected from the Dark Web, the differences in the results between the analysis services, and the malicious classification of files. The results reveal that about 30% of the harvested executable files are considered malicious by the malware analysis tools.