Developed a Technical Solution Guide within the Azure/AzureLocal-Supportability repository to address Solution Upgrade failures occurring at the SetTrustedHost step due to restrictive Group Policy settings. The guide outlined a clear troubleshooting process, enabling administrators to modify Group Policy Objects and resume upgrades without disruption. Leveraging expertise in system administration, technical writing, and troubleshooting, the work focused on improving upgrade reliability for Windows environments. Authored in Markdown, the documentation provided actionable steps that reduced the likelihood of post-upgrade support escalations. This contribution enhanced the overall upgrade experience by aligning technical guidance with real-world deployment challenges in enterprise settings.