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If care is not taken with the quoting of literals, the expression language (OGNL) will misinterpret a char as a String.

<ww<s:if test="#myObj.myStringaStringProperty == 'A'">
  Why doesn't this work when myString is equal to A?
</wws:if>

OGNL will interpret 'A' as a char type and not a string. Simple solution - The solution is simple: flip the double and single quotes.

<ww<s:if test='#myObj.myStringaStringProperty == "A"'>
  This works!
</wws:if>

Alternatively, you can Another solution is to escape the double quotes in the String:.

<ww<s:if test="#myObj.myStringaStringProperty == \"A\"">
  This works too!
</wws:if>