diff --git a/spock-core/src/main/java/org/spockframework/runtime/extension/builtin/PreconditionContext.java b/spock-core/src/main/java/org/spockframework/runtime/extension/builtin/PreconditionContext.java
index 1bebf9fa7c..cad33cc740 100644
--- a/spock-core/src/main/java/org/spockframework/runtime/extension/builtin/PreconditionContext.java
+++ b/spock-core/src/main/java/org/spockframework/runtime/extension/builtin/PreconditionContext.java
@@ -24,13 +24,14 @@
 import spock.lang.IgnoreIf;
 import spock.lang.PendingFeatureIf;
 import spock.lang.Requires;
+import spock.lang.Specification;
 import spock.util.environment.Jvm;
 import spock.util.environment.OperatingSystem;
 
 /**
  * The context (delegate) for a {@link Requires}, {@link IgnoreIf} or {@link PendingFeatureIf} condition.
  */
-public class PreconditionContext {
+public class PreconditionContext<S extends Specification> {
   private final Object theSharedInstance;
   private final Object theInstance;
   private final Map<String, Object> dataVariables;
@@ -88,11 +89,11 @@ public Jvm getJvm() {
    * @since 2.0
    * @return the test instance
    */
-  public Object getInstance() {
+  public S getInstance() {
     if (theInstance == null) {
       throw new InstanceContextException();
     }
-    return theInstance;
+    return (S) theInstance;
   }
 
   /**
@@ -103,11 +104,11 @@ public Object getInstance() {
    * @since 2.1
    * @return the shared instance
    */
-  public Object getShared() {
+  public S getShared() {
     if (theSharedInstance == null) {
       throw new SharedContextException();
     }
-    return theSharedInstance;
+    return (S) theSharedInstance;
   }
 
   /**
diff --git a/spock-core/src/main/java/org/spockframework/runtime/extension/builtin/RetryConditionContext.java b/spock-core/src/main/java/org/spockframework/runtime/extension/builtin/RetryConditionContext.java
index 560075f225..ed9d9a57f1 100644
--- a/spock-core/src/main/java/org/spockframework/runtime/extension/builtin/RetryConditionContext.java
+++ b/spock-core/src/main/java/org/spockframework/runtime/extension/builtin/RetryConditionContext.java
@@ -1,9 +1,11 @@
 package org.spockframework.runtime.extension.builtin;
 
+import spock.lang.Specification;
+
 /**
  * The context (delegate) for a {@link spock.lang.Retry} condition.
  */
-public class RetryConditionContext {
+public class RetryConditionContext<S extends Specification> {
 
   private final Object instance;
   private final Throwable failure;
@@ -27,8 +29,8 @@ public Throwable getFailure() {
    *
    * @return the current {@code Specification} instance
    */
-  public Object getInstance() {
-    return instance;
+  public S getInstance() {
+    return (S) instance;
   }
 
 }
diff --git a/spock-core/src/main/resources/dsld/spk.dsld b/spock-core/src/main/resources/dsld/spock_tests.dsld
similarity index 59%
rename from spock-core/src/main/resources/dsld/spk.dsld
rename to spock-core/src/main/resources/dsld/spock_tests.dsld
index fe900dbd36..5fd5bd32b7 100644
--- a/spock-core/src/main/resources/dsld/spk.dsld
+++ b/spock-core/src/main/resources/dsld/spock_tests.dsld
@@ -14,6 +14,7 @@
 
 package dsld
 
+import org.codehaus.groovy.ast.*
 import org.codehaus.groovy.ast.expr.*
 
 assertVersion(groovyEclipse: "2.7.2") // tested against this version
@@ -50,3 +51,29 @@ contribute(
   }
 }
 
+
+// From https://issues.apache.org/jira/browse/GROOVY-9510
+// Properly resolve the delegatesTo for the closures of these extensions
+def hasPrecondition = { annotatedBy(name('spock.lang.Requires') | name('spock.lang.IgnoreIf') | name('spock.lang.PendingFeatureIf')) }
+
+contribute(inClosure() & isThisType() & bind(classes: enclosingClass(subType('spock.lang.Specification')))
+ & (enclosingClass(conditions: hasPrecondition()) | enclosingMethod(conditions: hasPrecondition()))) {
+  for (AnnotationNode pre : conditions) {
+    def condition = pre.getMember('value')
+    if (condition.getCode().is(currentNode)) {
+      delegateType = resolver.resolve("org.spockframework.runtime.extension.builtin.PreconditionContext<${classes[0].getName()}>")
+      return
+    }
+  }
+}
+
+contribute(inClosure() & isThisType() & bind(classes: enclosingClass(subType('spock.lang.Specification')))
+ & (enclosingClass(annotations: annotatedBy('spock.lang.Retry')) | enclosingMethod(annotations: annotatedBy('spock.lang.Retry')))) {
+  for (AnnotationNode retry : annotations) {
+    def condition = retry.getMember('condition')
+    if (condition.getCode().is(currentNode)) {
+      delegateType = resolver.resolve("org.spockframework.runtime.extension.builtin.RetryConditionContext<${classes[0].getName()}>")
+      return
+    }
+  }
+}
diff --git a/spock-core/src/main/resources/org/spockframework/idea/spock.gdsl b/spock-core/src/main/resources/org/spockframework/idea/spock.gdsl
index f3b2f5ffe5..0a2746dd87 100644
--- a/spock-core/src/main/resources/org/spockframework/idea/spock.gdsl
+++ b/spock-core/src/main/resources/org/spockframework/idea/spock.gdsl
@@ -45,3 +45,14 @@ contributor(ctx, {
 })
 
 
+// From https://issues.apache.org/jira/browse/GROOVY-9510
+// Properly resolve the delegatesTo for the closures of these extensions
+def conditionalExtensions = ['spock.lang.Requires', 'spock.lang.IgnoreIf', 'spock.lang.PendingFeatureIf']
+        .collect { annot -> context(ctype: "spock.lang.Specification", scope: closureScope(annotationName: annot))}
+contributor(conditionalExtensions, {
+    delegatesTo(findClass('org.spockframework.runtime.extension.builtin.PreconditionContext'))
+})
+
+contributor(context(ctype: "spock.lang.Specification", scope: closureScope(annotationName: 'spock.lang.Retry')), {
+    delegatesTo(findClass('org.spockframework.runtime.extension.builtin.RetryConditionContext'))
+})