I ended up writing a plugin for this issue: https://.unrealengine.com/t/asset-tab-manager-manage-asset-tabs-save-and-load-tab-sessions-recover-previously-open-tabs-even-after-a-crash/623632
The plugin remembers your currently open tabs every time a new asset is opened so in the event you aren’t prompted to restore your session by the engine, you can restore what you want from the plugin’s automatic backup.