From https://www.mediawiki.org/wiki/Talk:Maps#Controversial_borders written by @Amire80:
I noticed some controversial borders at https://maps.wikimedia.org :
- The border between Crimea and Kherson is shown as international, which is the Russian Federation POV.
- South Ossetia and Abkhazia are shown as countries, which is the Russian Federation POV.
- The border of Kosovo looks like a border of an independent country (Kosovan POV), but it doesn't have a country name (weird POV ;) ).
- As a technically opposite example, there's no border in the middle of Cyprus (Greek POV), but there is a label for the Turkish Republic of Northern Cyprus (Turkish POV).
- The border between Israel and Syria is shown according to the Israeli POV.
There are possibly more issues of this kind. Wikipedias usually show maps of disputed territories quite well. For example, maps of Russia and Ukraine usually show Crimea in a special color - even in the Russian Wikipedia. I understand that at the moment Wikimedia's maps service probably just takes whatever OSM provides, but ideally it should do something similar to what the Wikipedias do and be as neutral as possible.