Internet of Things (IoT) products became recently an essential part of any home in conjunction with the great advancements in internet speeds and services. The invention of IoT based devices became an easy task that could be performed through the widely available IoT development boards. Raspberry Pi is considered one of the advanced development boards that have high hardware capabilities with a reasonable price. Unfortunately, the security aspect of such products is overlooked by the developers, revealing a huge amount of threats that result in invading the privacy and the security of the users. In this research, we directed our study to SSH due to its extensive adoption by the developers. It was found that due to the nature of the Raspberry Pi and development boards, the Raspberry Pi generates predictable and weak keys which make it easy to be utilized by MiTM attack. In this paper, Man in The Middle (MiTM) attack was conducted to examine the security of different variations provided by the SSH service, and various hardening approaches were proposed to resolve the issue of SSH weak implementation and weak keys.