Version: 1.50.1 (system setup)
Commit: d2e414d
Date: 2020-10-13T15:06:15.712Z
Electron: 9.2.1
Chrome: 83.0.4103.122
Node.js: 12.14.1
V8: 8.3.110.13-electron.0
OS: Windows_NT x64 10.0.19041

Note: I am aware of #92823, but this is a larger issue with settings tooltips for anyOf settings. I am about to go fix that specific case by writing extra description for that particular setting.

Steps to Reproduce:

1. Go into the user settings page and search for font ligatures; click on the item there
2. You get this, and think you can only turn it on/off: [caption: "Enable/Disable font ligatures" in a tooltip for editor.fontLigatures on a line with "editor.fontLigatures": null]
   
3. Find out somehow that it allows strings and get this [also, assuming you think of mousing over it once you put the RHS in]? But what's a font-feature-settings [requires the user has domain knowledge of CSS]? [caption: "Explicit font-feature-settings" in a tooltip for editor.fontLigatures on a line with "editor.fontLigatures": ""]
   

Additionally, if you were to type in "editor.fontLigatures" and see the intellisense, it wouldn't help much: [caption: "Configures font ligatures or font features" in an intellisense box as a suggestion for "editor.font"]

A PR is incoming to change all three of these strings to mitigate the UI issue for editor.fontLigatures specifically, but the UI should also be changed in these tooltips so it shows the description (last screenshot) above both the string and boolean setting types. I'm not proficient enough in TypeScript/VSCode internals to know where to start investigating the tooltip, so I'd appreciate if someone takes this on.

Does this issue occur when all extensions are disabled?: Yes/No
Yes