Solution 29530: Install Handheld OS Option Grayed Out on TI-Nspire™ Family Software.
How do I update the TI-Nspire handheld OS (Operating System) if "Check for Handheld OS Update" and "Install Handheld OS" are grayed out?If unable to update your TI-Nspire OS through the TI-Nspire family software, first try the options "Check for Handheld OS Update" (within the Help menu) and "Install Handheld OS" (within the Tools menu).
If both of these options are grayed out, please see Troubleshooting Connectivity Issues Between TI Graphing Calculators and Computers.
Next, confirm that the handheld is being recognized by the software by clicking on "Content Explorer" beneath the Documents Toolbox. You should see the handheld listed within the section for Connected Handhelds.
If the above Install Handheld OS options are still grayed out, please see Updating the TI-Nspire™ Family Handheld Operating System.