diff --git a/src/main/java/ch/njol/skript/ScriptLoader.java b/src/main/java/ch/njol/skript/ScriptLoader.java
index 411323f9795..dac3cc17596 100644
--- a/src/main/java/ch/njol/skript/ScriptLoader.java
+++ b/src/main/java/ch/njol/skript/ScriptLoader.java
@@ -962,7 +962,7 @@ public static ArrayList<TriggerItem> loadItems(SectionNode node) {
 			if (!SkriptParser.validateLine(expr))
 				continue;
 
-			TriggerItem item;
+			TriggerItem item = null;
 			if (subNode instanceof SimpleNode) {
 				long start = System.currentTimeMillis();
 				item = Statement.parse(expr, items, "Can't understand this condition/effect: " + expr);
@@ -982,13 +982,13 @@ public static ArrayList<TriggerItem> loadItems(SectionNode node) {
 					Skript.debug(SkriptColor.replaceColorChar(parser.getIndentation() + item.toString(null, true)));
 
 				items.add(item);
-			} else if (subNode instanceof SectionNode) {
+			} else if (subNode instanceof SectionNode subSection) {
 				TypeHints.enterScope(); // Begin conditional type hints
 
 				RetainingLogHandler handler = SkriptLogger.startRetainingLog();
 				find_section:
 				try {
-					item = Section.parse(expr, "Can't understand this section: " + expr, (SectionNode) subNode, items);
+					item = Section.parse(expr, "Can't understand this section: " + expr, subSection, items);
 					if (item != null)
 						break find_section;
 
@@ -996,7 +996,7 @@ public static ArrayList<TriggerItem> loadItems(SectionNode node) {
 					RetainingLogHandler backup = handler.backup();
 					handler.clear();
 
-					item = Statement.parse(expr, "Can't understand this condition/effect: " + expr, (SectionNode) subNode, items);
+					item = Statement.parse(expr, "Can't understand this condition/effect: " + expr, subSection, items);
 
 					if (item != null)
 						break find_section;
@@ -1013,12 +1013,14 @@ public static ArrayList<TriggerItem> loadItems(SectionNode node) {
 					}
 					continue;
 				} finally {
+					RetainingLogHandler afterParse = handler.backup();
+					handler.clear();
 					handler.printLog();
+					if (item != null && (Skript.debug() || subNode.debug()))
+						Skript.debug(SkriptColor.replaceColorChar(parser.getIndentation() + item.toString(null, true)));
+					afterParse.printLog();
 				}
 
-				if (Skript.debug() || subNode.debug())
-					Skript.debug(SkriptColor.replaceColorChar(parser.getIndentation() + item.toString(null, true)));
-
 				items.add(item);
 
 				// Destroy these conditional type hints
diff --git a/src/main/java/ch/njol/skript/sections/SecConditional.java b/src/main/java/ch/njol/skript/sections/SecConditional.java
index 02830488cc6..143976fd248 100644
--- a/src/main/java/ch/njol/skript/sections/SecConditional.java
+++ b/src/main/java/ch/njol/skript/sections/SecConditional.java
@@ -15,6 +15,7 @@
 import ch.njol.skript.patterns.PatternCompiler;
 import ch.njol.skript.patterns.SkriptPattern;
 import ch.njol.skript.util.Patterns;
+import ch.njol.skript.util.SkriptColor;
 import ch.njol.util.Kleenean;
 import com.google.common.collect.Iterables;
 import org.bukkit.event.Event;
@@ -203,6 +204,17 @@ public boolean init(Expression<?>[] exprs,
 			if (conditionals.isEmpty())
 				return false;
 
+			/*
+				This allows the embedded multilined conditions to be properly debugged.
+				Debugs are caught within the RetainingLogHandler in ScriptLoader#loadItems
+				Which will be printed after the debugged section (e.g 'if all')
+			 */
+			if ((Skript.debug() || sectionNode.debug()) && conditionals.size() > 1) {
+				String indentation = getParser().getIndentation() + "    ";
+				for (Conditional<?> condition : conditionals)
+					Skript.debug(indentation + SkriptColor.replaceColorChar(condition.toString(null, true)));
+			}
+
 			conditional = Conditional.compound(ifAny ? Operator.OR : Operator.AND, conditionals);
 		}