diff --git a/src/main/java/ch/njol/skript/conditions/CondAlphanumeric.java b/src/main/java/ch/njol/skript/conditions/CondAlphanumeric.java
index 01702442428..f20e7467bd5 100644
--- a/src/main/java/ch/njol/skript/conditions/CondAlphanumeric.java
+++ b/src/main/java/ch/njol/skript/conditions/CondAlphanumeric.java
@@ -1,5 +1,7 @@
 package ch.njol.skript.conditions;
 
+import ch.njol.skript.lang.Literal;
+import ch.njol.skript.lang.SimplifiedCondition;
 import org.apache.commons.lang.StringUtils;
 import org.bukkit.event.Event;
 import org.jetbrains.annotations.Nullable;
@@ -42,7 +44,14 @@ public boolean init(Expression<?>[] exprs, int matchedPattern, Kleenean isDelaye
 	public boolean check(Event e) {
 		return isNegated() ^ strings.check(e, StringUtils::isAlphanumeric);
 	}
-	
+
+	@Override
+	public Condition simplify() {
+		if (strings instanceof Literal<String>)
+			return SimplifiedCondition.fromCondition(this);
+		return this;
+	}
+
 	@Override
 	public String toString(@Nullable Event e, boolean debug) {
 		return strings.toString(e, debug) + " is" + (isNegated() ? "n't" : "") + " alphanumeric";
diff --git a/src/main/java/ch/njol/skript/conditions/CondCompare.java b/src/main/java/ch/njol/skript/conditions/CondCompare.java
index 74e5f96e7ae..b7ec5aee9c7 100644
--- a/src/main/java/ch/njol/skript/conditions/CondCompare.java
+++ b/src/main/java/ch/njol/skript/conditions/CondCompare.java
@@ -10,6 +10,7 @@
 import ch.njol.skript.lang.Expression;
 import ch.njol.skript.lang.ExpressionList;
 import ch.njol.skript.lang.Literal;
+import ch.njol.skript.lang.SimplifiedCondition;
 import ch.njol.skript.lang.SkriptParser.ParseResult;
 import ch.njol.skript.lang.UnparsedLiteral;
 import ch.njol.skript.lang.VerboseAssert;
@@ -397,6 +398,13 @@ private boolean compareLists(Event event) {
 		return shouldMatch;
 	}
 
+	@Override
+	public Condition simplify() {
+		if (first instanceof Literal<?> && second instanceof Literal<?> && (third == null || third instanceof Literal<?>))
+			return SimplifiedCondition.fromCondition(this);
+		return this;
+	}
+
 	@Override
 	public String toString(final @Nullable Event event, final boolean debug) {
 		String s;
diff --git a/src/main/java/ch/njol/skript/conditions/CondContains.java b/src/main/java/ch/njol/skript/conditions/CondContains.java
index 1aa5d9ac245..3965e5b0c8e 100644
--- a/src/main/java/ch/njol/skript/conditions/CondContains.java
+++ b/src/main/java/ch/njol/skript/conditions/CondContains.java
@@ -3,29 +3,30 @@
 import ch.njol.skript.Skript;
 import ch.njol.skript.SkriptConfig;
 import ch.njol.skript.aliases.ItemType;
-import ch.njol.skript.lang.VerboseAssert;
-import ch.njol.skript.lang.util.common.AnyContains;
-import ch.njol.skript.util.LiteralUtils;
-import org.skriptlang.skript.lang.comparator.Relation;
 import ch.njol.skript.doc.Description;
 import ch.njol.skript.doc.Examples;
 import ch.njol.skript.doc.Name;
 import ch.njol.skript.doc.Since;
 import ch.njol.skript.lang.Condition;
 import ch.njol.skript.lang.Expression;
+import ch.njol.skript.lang.Literal;
+import ch.njol.skript.lang.SimplifiedCondition;
 import ch.njol.skript.lang.SkriptParser.ParseResult;
+import ch.njol.skript.lang.VerboseAssert;
 import ch.njol.skript.lang.util.SimpleExpression;
-import org.skriptlang.skript.lang.comparator.Comparators;
+import ch.njol.skript.lang.util.common.AnyContains;
+import ch.njol.skript.util.LiteralUtils;
 import ch.njol.util.Kleenean;
 import ch.njol.util.StringUtils;
 import org.bukkit.event.Event;
 import org.bukkit.inventory.Inventory;
 import org.bukkit.inventory.ItemStack;
-import org.skriptlang.skript.lang.converter.Converters;
 import org.jetbrains.annotations.Nullable;
+import org.skriptlang.skript.lang.comparator.Comparators;
+import org.skriptlang.skript.lang.comparator.Relation;
+import org.skriptlang.skript.lang.converter.Converters;
 
 import java.util.Arrays;
-import java.util.List;
 import java.util.Objects;
 import java.util.StringJoiner;
 
@@ -183,6 +184,13 @@ public String getReceivedMessage(Event event) {
 		return joiner.toString();
 	}
 
+	@Override
+	public Condition simplify() {
+		if (containers instanceof Literal<?> && items instanceof Literal<?>)
+			return SimplifiedCondition.fromCondition(this);
+		return this;
+	}
+
 	@Override
 	public String toString(@Nullable Event e, boolean debug) {
 		return containers.toString(e, debug) + (isNegated() ? " doesn't contain " : " contains ") + items.toString(e, debug);
diff --git a/src/main/java/ch/njol/skript/conditions/CondDate.java b/src/main/java/ch/njol/skript/conditions/CondDate.java
index 473dc9423b7..88b0086b596 100644
--- a/src/main/java/ch/njol/skript/conditions/CondDate.java
+++ b/src/main/java/ch/njol/skript/conditions/CondDate.java
@@ -1,5 +1,7 @@
 package ch.njol.skript.conditions;
 
+import ch.njol.skript.lang.Literal;
+import ch.njol.skript.lang.SimplifiedCondition;
 import org.bukkit.event.Event;
 import org.jetbrains.annotations.Nullable;
 
@@ -58,7 +60,14 @@ public boolean check(final Event e) {
 						timespan -> now - date.getTime() >= timespan.getAs(Timespan.TimePeriod.MILLISECOND)
 				), isNegated());
 	}
-	
+
+	@Override
+	public Condition simplify() {
+		if (date instanceof Literal<Date> && delta instanceof Literal<Timespan>)
+			return SimplifiedCondition.fromCondition(this);
+		return this;
+	}
+
 	@Override
 	public String toString(final @Nullable Event e, final boolean debug) {
 		return date.toString(e, debug) + " was " + (isNegated() ? "less" : "more") + " than " + delta.toString(e, debug) + " ago";
diff --git a/src/main/java/ch/njol/skript/conditions/CondIsFuel.java b/src/main/java/ch/njol/skript/conditions/CondIsFuel.java
index f124f183a6b..9a303e97c20 100644
--- a/src/main/java/ch/njol/skript/conditions/CondIsFuel.java
+++ b/src/main/java/ch/njol/skript/conditions/CondIsFuel.java
@@ -1,15 +1,16 @@
 package ch.njol.skript.conditions;
 
-import org.bukkit.Material;
-
 import ch.njol.skript.Skript;
 import ch.njol.skript.aliases.ItemType;
 import ch.njol.skript.conditions.base.PropertyCondition;
 import ch.njol.skript.doc.Description;
 import ch.njol.skript.doc.Examples;
 import ch.njol.skript.doc.Name;
-import ch.njol.skript.doc.RequiredPlugins;
 import ch.njol.skript.doc.Since;
+import ch.njol.skript.lang.Condition;
+import ch.njol.skript.lang.Literal;
+import ch.njol.skript.lang.SimplifiedCondition;
+import org.bukkit.Material;
 
 @Name("Is Fuel")
 @Description("Checks whether an item can be used as fuel in a furnace.")
@@ -32,7 +33,14 @@ public class CondIsFuel extends PropertyCondition<ItemType> {
 	public boolean check(ItemType item) {
 		return item.getMaterial().isFuel();
 	}
-	
+
+	@Override
+	public Condition simplify() {
+		if (getExpr() instanceof Literal<? extends ItemType>)
+			return SimplifiedCondition.fromCondition(this);
+		return this;
+	}
+
 	@Override
 	protected String getPropertyName() {
 		return "fuel";
diff --git a/src/main/java/ch/njol/skript/conditions/CondIsInfinite.java b/src/main/java/ch/njol/skript/conditions/CondIsInfinite.java
index 9d76f4b0d88..12e3fb944da 100644
--- a/src/main/java/ch/njol/skript/conditions/CondIsInfinite.java
+++ b/src/main/java/ch/njol/skript/conditions/CondIsInfinite.java
@@ -5,6 +5,9 @@
 import ch.njol.skript.doc.Example;
 import ch.njol.skript.doc.Name;
 import ch.njol.skript.doc.Since;
+import ch.njol.skript.lang.Condition;
+import ch.njol.skript.lang.Literal;
+import ch.njol.skript.lang.SimplifiedCondition;
 import ch.njol.skript.util.Timespan;
 import org.bukkit.potion.PotionEffect;
 
@@ -28,6 +31,13 @@ public boolean check(Object object) {
 		return false;
 	}
 
+	@Override
+	public Condition simplify() {
+		if (getExpr() instanceof Literal<?>)
+			return SimplifiedCondition.fromCondition(this);
+		return this;
+	}
+
 	@Override
 	protected String getPropertyName() {
 		return "infinite";
diff --git a/src/main/java/ch/njol/skript/conditions/CondIsVectorNormalized.java b/src/main/java/ch/njol/skript/conditions/CondIsVectorNormalized.java
index 7c4851d8470..4267bad9992 100644
--- a/src/main/java/ch/njol/skript/conditions/CondIsVectorNormalized.java
+++ b/src/main/java/ch/njol/skript/conditions/CondIsVectorNormalized.java
@@ -5,6 +5,9 @@
 import ch.njol.skript.doc.Examples;
 import ch.njol.skript.doc.Name;
 import ch.njol.skript.doc.Since;
+import ch.njol.skript.lang.Condition;
+import ch.njol.skript.lang.Literal;
+import ch.njol.skript.lang.SimplifiedCondition;
 import org.bukkit.util.Vector;
 
 @Name("Is Normalized")
@@ -21,7 +24,14 @@ public class CondIsVectorNormalized extends PropertyCondition<Vector> {
 	public boolean check(Vector vector) {
 		return vector.isNormalized();
 	}
-	
+
+	@Override
+	public Condition simplify() {
+		if (getExpr() instanceof Literal<? extends Vector>)
+			return SimplifiedCondition.fromCondition(this);
+		return this;
+	}
+
 	@Override
 	protected String getPropertyName() {
 		return "normalized";
diff --git a/src/main/java/ch/njol/skript/conditions/CondMatches.java b/src/main/java/ch/njol/skript/conditions/CondMatches.java
index 6ce5facb581..d29643ffcc2 100644
--- a/src/main/java/ch/njol/skript/conditions/CondMatches.java
+++ b/src/main/java/ch/njol/skript/conditions/CondMatches.java
@@ -1,12 +1,6 @@
 
 package ch.njol.skript.conditions;
 
-import java.util.Arrays;
-import java.util.regex.Pattern;
-
-import org.bukkit.event.Event;
-import org.jetbrains.annotations.Nullable;
-
 import ch.njol.skript.Skript;
 import ch.njol.skript.doc.Description;
 import ch.njol.skript.doc.Examples;
@@ -14,8 +8,15 @@
 import ch.njol.skript.doc.Since;
 import ch.njol.skript.lang.Condition;
 import ch.njol.skript.lang.Expression;
+import ch.njol.skript.lang.Literal;
+import ch.njol.skript.lang.SimplifiedCondition;
 import ch.njol.skript.lang.SkriptParser.ParseResult;
 import ch.njol.util.Kleenean;
+import org.bukkit.event.Event;
+import org.jetbrains.annotations.Nullable;
+
+import java.util.Arrays;
+import java.util.regex.Pattern;
 
 @Name("Matches")
 @Description("Checks whether the defined strings match the input regexes (Regular expressions).")
@@ -75,7 +76,14 @@ public boolean check(Event e) {
 	public boolean matches(String str, Pattern pattern) {
 		return partial ? pattern.matcher(str).find() : str.matches(pattern.pattern());
 	}
-	
+
+	@Override
+	public Condition simplify() {
+		if (strings instanceof Literal<String> && regex instanceof Literal<String>)
+			return SimplifiedCondition.fromCondition(this);
+		return this;
+	}
+
 	@Override
 	public String toString(@Nullable Event e, boolean debug) {
 		return strings.toString(e, debug) + " " + (isNegated() ? "doesn't match" : "matches") + " " + regex.toString(e, debug);
diff --git a/src/main/java/ch/njol/skript/conditions/CondMinecraftVersion.java b/src/main/java/ch/njol/skript/conditions/CondMinecraftVersion.java
index 682b6a144cd..6160a400219 100644
--- a/src/main/java/ch/njol/skript/conditions/CondMinecraftVersion.java
+++ b/src/main/java/ch/njol/skript/conditions/CondMinecraftVersion.java
@@ -1,5 +1,7 @@
 package ch.njol.skript.conditions;
 
+import ch.njol.skript.lang.Literal;
+import ch.njol.skript.lang.SimplifiedCondition;
 import org.bukkit.event.Event;
 import org.jetbrains.annotations.Nullable;
 
@@ -40,7 +42,14 @@ public boolean check(Event e) {
 		String ver = version.getSingle(e);
 		return ver != null ? Skript.isRunningMinecraft(new Version(ver)) ^ isNegated() : false;
 	}
-	
+
+	@Override
+	public Condition simplify() {
+		if (version instanceof Literal<String>)
+			return SimplifiedCondition.fromCondition(this);
+		return this;
+	}
+
 	@Override
 	public String toString(@Nullable Event e, boolean debug) {
 		return "is running minecraft " + version.toString(e, debug);
diff --git a/src/main/java/ch/njol/skript/conditions/CondPastFuture.java b/src/main/java/ch/njol/skript/conditions/CondPastFuture.java
index 2f8748f1a73..916a35e653a 100644
--- a/src/main/java/ch/njol/skript/conditions/CondPastFuture.java
+++ b/src/main/java/ch/njol/skript/conditions/CondPastFuture.java
@@ -9,6 +9,8 @@
 import ch.njol.skript.lang.Condition;
 import ch.njol.skript.lang.Expression;
 import ch.njol.skript.lang.ExpressionList;
+import ch.njol.skript.lang.Literal;
+import ch.njol.skript.lang.SimplifiedCondition;
 import ch.njol.skript.lang.SkriptParser.ParseResult;
 import ch.njol.skript.util.Date;
 import ch.njol.util.Kleenean;
@@ -78,6 +80,13 @@ public boolean check(Event event) {
 		return dates.check(event, date -> date.compareTo(new Date()) < 0, isNegated());
 	}
 
+	@Override
+	public Condition simplify() {
+		if (dates instanceof Literal<Date>)
+			return SimplifiedCondition.fromCondition(this);
+		return this;
+	}
+
 	@Override
 	public String toString(@Nullable Event event, boolean debug) {
 		return dates.toString(event, debug) + (dates.isSingle() ? " is"  : " are") + " in the" + (isFuture ? " future" : " past");
diff --git a/src/main/java/ch/njol/skript/conditions/CondStartsEndsWith.java b/src/main/java/ch/njol/skript/conditions/CondStartsEndsWith.java
index 205db7eca53..463b3d837f5 100644
--- a/src/main/java/ch/njol/skript/conditions/CondStartsEndsWith.java
+++ b/src/main/java/ch/njol/skript/conditions/CondStartsEndsWith.java
@@ -1,5 +1,7 @@
 package ch.njol.skript.conditions;
 
+import ch.njol.skript.lang.Literal;
+import ch.njol.skript.lang.SimplifiedCondition;
 import org.bukkit.event.Event;
 import org.jetbrains.annotations.Nullable;
 
@@ -80,7 +82,14 @@ public boolean check(Event e) {
 			},
 			isNegated());
 	}
-	
+
+	@Override
+	public Condition simplify() {
+		if (strings instanceof Literal<String> && affix instanceof Literal<String>)
+			return SimplifiedCondition.fromCondition(this);
+		return this;
+	}
+
 	@Override
 	public String toString(@Nullable Event e, boolean debug) {
 		if (isNegated())
diff --git a/src/main/java/ch/njol/skript/lang/Condition.java b/src/main/java/ch/njol/skript/lang/Condition.java
index 40f76710124..9e130d013e9 100644
--- a/src/main/java/ch/njol/skript/lang/Condition.java
+++ b/src/main/java/ch/njol/skript/lang/Condition.java
@@ -3,6 +3,7 @@
 import ch.njol.skript.Skript;
 import ch.njol.skript.conditions.base.PropertyCondition;
 import ch.njol.skript.config.Node;
+import ch.njol.skript.lang.simplification.Simplifiable;
 import ch.njol.skript.lang.util.SimpleExpression;
 import ch.njol.util.Kleenean;
 import org.bukkit.event.Event;
@@ -22,7 +23,7 @@
  *
  * @see Skript#registerCondition(Class, String...)
  */
-public abstract class Condition extends Statement implements Conditional<Event>, SyntaxRuntimeErrorProducer {
+public abstract class Condition extends Statement implements Conditional<Event>, SyntaxRuntimeErrorProducer, Simplifiable<Condition> {
 
 	public enum ConditionType {
 		/**
@@ -117,6 +118,11 @@ public Node getNode() {
 		return "condition";
 	}
 
+	@Override
+	public Condition simplify() {
+		return this;
+	}
+
 	/**
 	 * Parse a raw string input as a condition.
 	 * 
diff --git a/src/main/java/ch/njol/skript/lang/SimplifiedCondition.java b/src/main/java/ch/njol/skript/lang/SimplifiedCondition.java
new file mode 100644
index 00000000000..6a9562660f3
--- /dev/null
+++ b/src/main/java/ch/njol/skript/lang/SimplifiedCondition.java
@@ -0,0 +1,99 @@
+package ch.njol.skript.lang;
+
+import ch.njol.skript.Skript;
+import ch.njol.skript.lang.SkriptParser.ParseResult;
+import ch.njol.skript.lang.parser.ParserInstance;
+import ch.njol.skript.lang.util.ContextlessEvent;
+import ch.njol.skript.test.runner.TestMode;
+import ch.njol.util.Kleenean;
+import org.bukkit.event.Event;
+import org.jetbrains.annotations.Nullable;
+import org.skriptlang.skript.lang.script.Script;
+import org.skriptlang.skript.lang.script.ScriptWarning;
+
+/**
+ * Represents a condition that can be simplified during initialization.
+ */
+public class SimplifiedCondition extends Condition {
+
+	/**
+	 * Creates a new {@link SimplifiedCondition} from a {@link Condition} by evaluating it with a {@link ContextlessEvent}.
+	 * Any expression used by {@code original} that requires specific event data cannot be safely simplified.
+	 *
+	 * @param original The original {@link Condition} to simplify.
+	 * @return A new {@link SimplifiedCondition}.
+	 */
+	public static Condition fromCondition(Condition original) {
+		return fromCondition(original, (!TestMode.ENABLED || TestMode.DEV_MODE));
+	}
+
+	/**
+	 * Creates a new {@link SimplifiedCondition} from a {@link Condition} by evaluating it with a {@link ContextlessEvent}.
+	 * Any expression used by {@code original} that requires specific event data cannot be safely simplified.
+	 *
+	 * @param original The original {@link Condition} to simplify.
+	 * @param warn Whether a warning for constant conditions should be outputted.
+	 * @return A new {@link SimplifiedCondition}.
+	 */
+	public static Condition fromCondition(Condition original, boolean warn) {
+		if (original instanceof SimplifiedCondition simplifiedCondition)
+			return simplifiedCondition;
+
+		Event event = ContextlessEvent.get();
+		boolean result = original.check(event);
+
+		if (warn) {
+			ParserInstance parser = ParserInstance.get();
+			Script script = parser.isActive() ? parser.getCurrentScript() : null;
+			if (script != null && !script.suppressesWarning(ScriptWarning.CONSTANT_CONDITION)) {
+				Skript.warning("The condition '" + original.toString(event, Skript.debug()) + "' will always be " + (result ? "true" : "false") + ".");
+			}
+		}
+
+		return new SimplifiedCondition(original, result);
+	}
+
+	private final Condition source;
+	private final boolean result;
+
+	/**
+	 * Constructs a new {@link SimplifiedCondition}.
+	 *
+	 * @param source The source {@link Condition} this was created from.
+	 * @param result The evaluated result from {@code source} via {@link Condition#check(Event)}.
+	 */
+	private SimplifiedCondition(Condition source, boolean result) {
+		this.source = source;
+		this.result = result;
+	}
+
+	/**
+	 * Returns the source {@link Condition} used to create this {@link SimplifiedCondition}.
+	 */
+	public Condition getSource() {
+		return source;
+	}
+
+	/**
+	 * Returns the result that was evaluated from {@link #source} during initialization.
+	 */
+	public boolean getResult() {
+		return result;
+	}
+
+	@Override
+	public boolean init(Expression<?>[] expressions, int matchedPattern, Kleenean isDelayed, ParseResult parseResult) {
+		throw new UnsupportedOperationException();
+	}
+
+	@Override
+	public boolean check(Event event) {
+		return result;
+	}
+
+	@Override
+	public String toString(@Nullable Event event, boolean debug) {
+		return source.toString(event, debug);
+	}
+
+}
diff --git a/src/main/java/ch/njol/skript/test/runner/CondMethodExists.java b/src/main/java/ch/njol/skript/test/runner/CondMethodExists.java
index a479fcb903c..f7b9307569e 100644
--- a/src/main/java/ch/njol/skript/test/runner/CondMethodExists.java
+++ b/src/main/java/ch/njol/skript/test/runner/CondMethodExists.java
@@ -2,6 +2,9 @@
 
 import ch.njol.skript.conditions.base.PropertyCondition;
 import ch.njol.skript.doc.NoDoc;
+import ch.njol.skript.lang.Condition;
+import ch.njol.skript.lang.Literal;
+import ch.njol.skript.lang.SimplifiedCondition;
 import org.apache.commons.lang.StringUtils;
 import org.bukkit.event.Event;
 import org.jetbrains.annotations.Nullable;
@@ -71,6 +74,13 @@ protected String getPropertyName() {
 		return "method exists";
 	}
 
+	@Override
+	public Condition simplify() {
+		if (!(signatures instanceof Literal<String>))
+			return this;
+		return SimplifiedCondition.fromCondition(this);
+	}
+
 	@Override
 	public String toString(@Nullable Event event, boolean debug) {
 		return "method " + signatures.toString(event, debug) + " exists";
diff --git a/src/main/java/org/skriptlang/skript/lang/script/ScriptWarning.java b/src/main/java/org/skriptlang/skript/lang/script/ScriptWarning.java
index 847cde014b6..1338040cb1d 100644
--- a/src/main/java/org/skriptlang/skript/lang/script/ScriptWarning.java
+++ b/src/main/java/org/skriptlang/skript/lang/script/ScriptWarning.java
@@ -1,7 +1,9 @@
 package org.skriptlang.skript.lang.script;
 
 import ch.njol.skript.Skript;
+import ch.njol.skript.lang.Condition;
 import ch.njol.skript.lang.Expression;
+import ch.njol.skript.lang.SimplifiedCondition;
 import ch.njol.skript.lang.SkriptParser;
 import ch.njol.skript.lang.parser.ParserInstance;
 import ch.njol.util.Kleenean;
@@ -41,7 +43,13 @@ public enum ScriptWarning {
 	/**
 	 * The code cannot be reached due to a previous statement stopping further execution
 	 */
-	UNREACHABLE_CODE("unreachable code");
+	UNREACHABLE_CODE("unreachable code"),
+
+	/**
+	 * A {@link Condition} can be simplified to {@link SimplifiedCondition}, which results in the assertion always passing or failing.
+	 */
+	CONSTANT_CONDITION("constant condition", "constant condition[s]")
+	;
 
 	private final String warningName;
 	private final String pattern;