When using WebExecute TypeElement, I get $Failed if I have a diacritics character in the submitted string. Here is a minimal example:
session = StartWebSession["Chrome"];
WebExecute["OpenPage"->"https://stackoverflow.com/questions/35126293/how-to-set-text-into-textarea-with-selenium-webdriver"];
textArea = First@WebExecute["LocateElements"->"XPath"->"//*[@id=\"wmd-input\"]"];
WebExecute["TypeElement"->{textArea, "à"}]
If I change "à" to "a", it works so far so good.
[update] It's a bug, see work around in the link below.
[updade2] Bug solved in version 12.1.1
crosspost in Stack Exchange
encoding bug parsing UTF8 in Mathematica