diff --git a/paper-api/src/main/java/org/bukkit/configuration/MemorySection.java b/paper-api/src/main/java/org/bukkit/configuration/MemorySection.java
index fe7762b989..3da7da3486 100644
--- a/paper-api/src/main/java/org/bukkit/configuration/MemorySection.java
+++ b/paper-api/src/main/java/org/bukkit/configuration/MemorySection.java
@@ -742,7 +742,12 @@ public class MemorySection implements ConfigurationSection {
             MemorySection sec = (MemorySection) section;
 
             for (Map.Entry<String, Object> entry : sec.map.entrySet()) {
-                output.put(createPath(section, entry.getKey(), this), entry.getValue());
+                // Because of the copyDefaults call potentially copying out of order, we must remove and then add in our saved order
+                // This means that default values we haven't set end up getting placed first
+                // See SPIGOT-4558 for an example using spigot.yml - watch subsections move around to default order
+                String childPath = createPath(section, entry.getKey(), this);
+                output.remove(childPath);
+                output.put(childPath, entry.getValue());
 
                 if (entry.getValue() instanceof ConfigurationSection) {
                     if (deep) {
diff --git a/paper-api/src/test/java/org/bukkit/configuration/ConfigurationSectionTest.java b/paper-api/src/test/java/org/bukkit/configuration/ConfigurationSectionTest.java
index 56a34f0b96..462fc0a71e 100644
--- a/paper-api/src/test/java/org/bukkit/configuration/ConfigurationSectionTest.java
+++ b/paper-api/src/test/java/org/bukkit/configuration/ConfigurationSectionTest.java
@@ -69,18 +69,21 @@ public abstract class ConfigurationSectionTest {
         ConfigurationSection section = getConfigurationSection();
         section.getRoot().options().copyDefaults(true);
 
+        // Fix for SPIGOT-4558 means that defaults will always be first
+        // This is a little bit unintuitive for section defaults when deep iterating keys / values as shown below
+        // But the API doesn't guarantee order & when serialized (using shallow getters) all is well
         section.set("bool", true);
         section.set("subsection.string", "test");
         section.addDefault("subsection.long", Long.MAX_VALUE);
         section.addDefault("int", 42);
 
         Map<String, Object> shallowValues = section.getValues(false);
-        assertArrayEquals(new String[] { "subsection", "int", "bool" }, shallowValues.keySet().toArray());
-        assertArrayEquals(new Object[] { section.getConfigurationSection("subsection"), 42, true }, shallowValues.values().toArray());
+        assertArrayEquals(new String[] { "int", "bool", "subsection" }, shallowValues.keySet().toArray());
+        assertArrayEquals(new Object[] { 42, true, section.getConfigurationSection("subsection") }, shallowValues.values().toArray());
 
         Map<String, Object> deepValues = section.getValues(true);
-        assertArrayEquals(new String[] { "subsection", "subsection.long", "int", "bool", "subsection.string" }, deepValues.keySet().toArray());
-        assertArrayEquals(new Object[] { section.getConfigurationSection("subsection"), Long.MAX_VALUE, 42, true, "test" }, deepValues.values().toArray());
+        assertArrayEquals(new String[] { "subsection.long", "int", "bool", "subsection",  "subsection.string" }, deepValues.keySet().toArray());
+        assertArrayEquals(new Object[] { Long.MAX_VALUE, 42, true, section.getConfigurationSection("subsection"), "test" }, deepValues.values().toArray());
     }
 
     @Test