diff --git a/element-template-generator/core/src/main/java/io/camunda/connector/generator/java/annotation/TemplateProperty.java b/element-template-generator/core/src/main/java/io/camunda/connector/generator/java/annotation/TemplateProperty.java
index f56ced13d7..016be635be 100644
--- a/element-template-generator/core/src/main/java/io/camunda/connector/generator/java/annotation/TemplateProperty.java
+++ b/element-template-generator/core/src/main/java/io/camunda/connector/generator/java/annotation/TemplateProperty.java
@@ -135,11 +135,37 @@ enum DefaultValueType {
     String name();
   }
 
+  enum EqualsBoolean {
+    TRUE,
+    FALSE,
+    NULL;
+
+    public static EqualsBoolean fromBoolean(Boolean value) {
+      if (value == null) {
+        return NULL;
+      } else if (value) {
+        return TRUE;
+      } else {
+        return FALSE;
+      }
+    }
+
+    public Boolean toBoolean() {
+      if (this == NULL) {
+        return null;
+      } else {
+        return this == TRUE;
+      }
+    }
+  }
+
   @interface PropertyCondition {
     String property();
 
     String equals() default "";
 
+    EqualsBoolean equalsBoolean() default EqualsBoolean.NULL;
+
     String[] oneOf() default {};
 
     NestedPropertyCondition[] allMatch() default {};
@@ -153,6 +179,8 @@ enum DefaultValueType {
     /** For string properties */
     String equals() default "";
 
+    EqualsBoolean equalsBoolean() default EqualsBoolean.NULL;
+
     String[] oneOf() default {};
 
     boolean isActive() default false;
diff --git a/element-template-generator/core/src/main/java/io/camunda/connector/generator/java/processor/TemplatePropertyFieldProcessor.java b/element-template-generator/core/src/main/java/io/camunda/connector/generator/java/processor/TemplatePropertyFieldProcessor.java
index 48f96053a5..2cb53621c4 100644
--- a/element-template-generator/core/src/main/java/io/camunda/connector/generator/java/processor/TemplatePropertyFieldProcessor.java
+++ b/element-template-generator/core/src/main/java/io/camunda/connector/generator/java/processor/TemplatePropertyFieldProcessor.java
@@ -22,6 +22,7 @@
 import io.camunda.connector.generator.dsl.PropertyCondition;
 import io.camunda.connector.generator.dsl.PropertyConstraints;
 import io.camunda.connector.generator.java.annotation.TemplateProperty;
+import io.camunda.connector.generator.java.annotation.TemplateProperty.EqualsBoolean;
 import io.camunda.connector.generator.java.annotation.TemplateProperty.NestedPropertyCondition;
 import io.camunda.connector.generator.java.util.TemplateGenerationContext;
 import java.lang.reflect.Field;
@@ -88,6 +89,7 @@ private PropertyCondition buildCondition(TemplateProperty propertyAnnotation) {
     validateCondition(
         conditionAnnotation.property(),
         conditionAnnotation.equals(),
+        conditionAnnotation.equalsBoolean(),
         conditionAnnotation.oneOf(),
         conditionAnnotation.allMatch());
     return transformToCondition(conditionAnnotation);
@@ -99,6 +101,9 @@ public static PropertyCondition transformToCondition(
     if (!conditionAnnotation.equals().isBlank()) {
       return new PropertyCondition.Equals(
           conditionAnnotation.property(), conditionAnnotation.equals());
+    } else if (conditionAnnotation.equalsBoolean() != TemplateProperty.EqualsBoolean.NULL) {
+      return new PropertyCondition.Equals(
+          conditionAnnotation.property(), conditionAnnotation.equalsBoolean().toBoolean());
     } else if (conditionAnnotation.oneOf().length > 0) {
       return new PropertyCondition.OneOf(
           conditionAnnotation.property(), Arrays.asList(conditionAnnotation.oneOf()));
@@ -119,11 +124,15 @@ public static PropertyCondition transformToNestedCondition(
     validateCondition(
         conditionAnnotation.property(),
         conditionAnnotation.equals(),
+        conditionAnnotation.equalsBoolean(),
         conditionAnnotation.oneOf(),
         new NestedPropertyCondition[] {});
     if (!conditionAnnotation.equals().isBlank()) {
       return new PropertyCondition.Equals(
           conditionAnnotation.property(), conditionAnnotation.equals());
+    } else if (conditionAnnotation.equalsBoolean() != TemplateProperty.EqualsBoolean.NULL) {
+      return new PropertyCondition.Equals(
+          conditionAnnotation.property(), conditionAnnotation.equalsBoolean().toBoolean());
     } else if (conditionAnnotation.oneOf().length > 0) {
       return new PropertyCondition.OneOf(
           conditionAnnotation.property(), Arrays.asList(conditionAnnotation.oneOf()));
@@ -135,16 +144,26 @@ public static PropertyCondition transformToNestedCondition(
   }
 
   private static void validateCondition(
-      String property, String equals, String[] oneOf, NestedPropertyCondition[] allMatch) {
+      String property,
+      String equals,
+      EqualsBoolean equalsBoolean,
+      String[] oneOf,
+      NestedPropertyCondition[] allMatch) {
     var equalsSet = !equals.isBlank();
+    var equalsBooleanSet = !equalsBoolean.equals(TemplateProperty.EqualsBoolean.NULL);
     var oneOfSet = oneOf != null && oneOf.length > 0;
     var allMatchSet = allMatch != null && allMatch.length > 0;
     // equalsBoolean always has a value, so it's not included in the check
     // if everything else is not set, we consider it an equalsBoolean condition
 
-    if (equalsSet && oneOfSet || equalsSet && allMatchSet || oneOfSet && allMatchSet) {
+    if (equalsSet && equalsBooleanSet
+        || equalsSet && oneOfSet
+        || equalsSet && allMatchSet
+        || oneOfSet && allMatchSet
+        || oneOfSet && equalsBooleanSet
+        || allMatchSet && equalsBooleanSet) {
       throw new IllegalStateException(
-          "Condition must have only one of 'equals', 'oneOf', 'isActive', or 'allMatch' set");
+          "Condition must have only one of 'equals', 'equalsBoolean', 'oneOf', 'isActive', or 'allMatch' set");
     }
     if (equalsSet && property.isBlank()) {
       throw new IllegalStateException("Condition 'equals' must have 'property' set");
diff --git a/element-template-generator/core/src/test/java/io/camunda/connector/generator/java/OutboundClassBasedTemplateGeneratorTest.java b/element-template-generator/core/src/test/java/io/camunda/connector/generator/java/OutboundClassBasedTemplateGeneratorTest.java
index 692cb01934..7770f8cdcb 100644
--- a/element-template-generator/core/src/test/java/io/camunda/connector/generator/java/OutboundClassBasedTemplateGeneratorTest.java
+++ b/element-template-generator/core/src/test/java/io/camunda/connector/generator/java/OutboundClassBasedTemplateGeneratorTest.java
@@ -554,9 +554,9 @@ void booleanProperty() {
     void booleanProperty_dependants() {
       var template = generator.generate(MyConnectorFunction.MinimallyAnnotated.class).getFirst();
       var dependsOnTrue = getPropertyById("dependsOnBooleanPropertyTrue", template);
-      assertThat(dependsOnTrue.getCondition()).isEqualTo(new Equals("booleanProperty", "true"));
+      assertThat(dependsOnTrue.getCondition()).isEqualTo(new Equals("booleanProperty", true));
       var dependsOnFalse = getPropertyById("dependsOnBooleanPropertyFalse", template);
-      assertThat(dependsOnFalse.getCondition()).isEqualTo(new Equals("booleanProperty", "false"));
+      assertThat(dependsOnFalse.getCondition()).isEqualTo(new Equals("booleanProperty", false));
     }
   }
 
diff --git a/element-template-generator/core/src/test/java/io/camunda/connector/generator/java/example/outbound/MyConnectorInput.java b/element-template-generator/core/src/test/java/io/camunda/connector/generator/java/example/outbound/MyConnectorInput.java
index 6cb6449a5f..a94d13b18f 100644
--- a/element-template-generator/core/src/test/java/io/camunda/connector/generator/java/example/outbound/MyConnectorInput.java
+++ b/element-template-generator/core/src/test/java/io/camunda/connector/generator/java/example/outbound/MyConnectorInput.java
@@ -21,6 +21,7 @@
 import io.camunda.connector.generator.java.annotation.TemplateDiscriminatorProperty;
 import io.camunda.connector.generator.java.annotation.TemplateProperty;
 import io.camunda.connector.generator.java.annotation.TemplateProperty.DefaultValueType;
+import io.camunda.connector.generator.java.annotation.TemplateProperty.EqualsBoolean;
 import io.camunda.connector.generator.java.annotation.TemplateProperty.PropertyCondition;
 import io.camunda.connector.generator.java.annotation.TemplateProperty.PropertyConstraints;
 import io.camunda.connector.generator.java.annotation.TemplateProperty.PropertyType;
@@ -96,11 +97,17 @@ public record MyConnectorInput(
         Boolean booleanProperty,
     @TemplateProperty(
             id = "dependsOnBooleanPropertyFalse",
-            condition = @PropertyCondition(property = "booleanProperty", equals = "false"))
+            condition =
+                @PropertyCondition(
+                    property = "booleanProperty",
+                    equalsBoolean = EqualsBoolean.FALSE))
         String dependsOnBooleanPropertyFalse,
     @TemplateProperty(
             id = "dependsOnBooleanPropertyTrue",
-            condition = @PropertyCondition(property = "booleanProperty", equals = "true"))
+            condition =
+                @PropertyCondition(
+                    property = "booleanProperty",
+                    equalsBoolean = EqualsBoolean.TRUE))
         String dependsOnBooleanPropertyTrue,
     @TemplateProperty(
             id = "mayBeEmptyOrRegexValidated",