Organizations are increasingly concerned about the impending End of Life (EoL) deadlines for Microsoft applications and systems, with many large enterprises seeking advice on upgrading Microsoft Teams and legacy technologies. Key products like Windows 10, Office 2019, and Exchange Server 2019 will reach end-of-support by October 2025, prompting urgent decisions to mitigate operational, security, and compliance risks. Statistics show that as of January 2025, Windows 10 and Windows 11 each hold a 49.4% market share in the UK, indicating that half of all desktops are nearing their EoL. Dedicated EoL hotlines have been established to assist companies with migration strategies for applications approaching EoL, emphasizing the need for internal resources and expertise to manage transitions effectively. The industry-standard ‘R approach’ includes methods like rehosting and retiring applications to facilitate migrations. Organizations are encouraged to migrate out-of-support applications into secure environments rather than directly altering them, while remaining vigilant about EoL deadlines and the complexities of legacy systems.