diff --git a/idea/jvm-debugger/jvm-debugger-util/src/org/jetbrains/kotlin/idea/debugger/CodeFragmentContextUtils.kt b/idea/jvm-debugger/jvm-debugger-util/src/org/jetbrains/kotlin/idea/debugger/CodeFragmentContextUtils.kt
index e9fa08a99dd..973b0c61a74 100644
--- a/idea/jvm-debugger/jvm-debugger-util/src/org/jetbrains/kotlin/idea/debugger/CodeFragmentContextUtils.kt
+++ b/idea/jvm-debugger/jvm-debugger-util/src/org/jetbrains/kotlin/idea/debugger/CodeFragmentContextUtils.kt
@@ -6,11 +6,12 @@
 package org.jetbrains.kotlin.idea.debugger
 
 import com.intellij.psi.*
+import com.intellij.psi.impl.source.tree.LeafPsiElement
 import com.intellij.psi.util.PsiTreeUtil
 import org.jetbrains.kotlin.asJava.classes.KtLightClass
 import org.jetbrains.kotlin.idea.debugger.KotlinEditorTextProvider.Companion.isAcceptedAsCodeFragmentContext
-import org.jetbrains.kotlin.psi.KtExpression
-import org.jetbrains.kotlin.psi.KtFile
+import org.jetbrains.kotlin.lexer.KtTokens
+import org.jetbrains.kotlin.psi.*
 import org.jetbrains.kotlin.psi.psiUtil.parents
 
 fun getContextElement(elementAt: PsiElement?): PsiElement? {
@@ -25,17 +26,41 @@ fun getContextElement(elementAt: PsiElement?): PsiElement? {
     }
 
     val containingFile = elementAt.containingFile
-    if (containingFile is PsiJavaFile) return elementAt
-    if (containingFile !is KtFile) return null
-
-    // elementAt can be PsiWhiteSpace when codeFragment is created from line start offset (in case of first opening EE window)
-    val lineStartOffset = if (elementAt is PsiWhiteSpace || elementAt is PsiComment) {
-        PsiTreeUtil.skipSiblingsForward(elementAt, PsiWhiteSpace::class.java, PsiComment::class.java)?.textOffset
-            ?: elementAt.textOffset
-    } else {
-        elementAt.textOffset
+    if (containingFile is PsiJavaFile) {
+        return elementAt
     }
 
+    if (containingFile !is KtFile) {
+        return null
+    }
+
+    val accurateElement = getAccurateContextElement(elementAt, containingFile)
+    if (accurateElement != null) {
+        return accurateElement
+    }
+
+    return containingFile
+}
+
+private fun getAccurateContextElement(elementAt: PsiElement, containingFile: KtFile): PsiElement? {
+    // elementAt can be PsiWhiteSpace when codeFragment is created from line start offset (in case of first opening EE window)
+    val elementAtSkippingWhitespaces = getElementSkippingWhitespaces(elementAt)
+
+    if (elementAtSkippingWhitespaces is LeafPsiElement && elementAtSkippingWhitespaces.elementType == KtTokens.RBRACE) {
+        val classBody = elementAtSkippingWhitespaces.parent as? KtClassBody
+        val classOrObject = classBody?.parent as? KtClassOrObject
+        var declarationParent = classOrObject?.parent
+        if (declarationParent is KtObjectLiteralExpression) {
+            declarationParent = declarationParent.parent
+        }
+
+        if (declarationParent != null) {
+            return getAccurateContextElement(declarationParent, containingFile)
+        }
+    }
+
+    val lineStartOffset = elementAtSkippingWhitespaces.textOffset
+
     val targetExpression = PsiTreeUtil.findElementOfClassAtOffset(containingFile, lineStartOffset, KtExpression::class.java, false)
 
     if (targetExpression != null) {
@@ -52,5 +77,16 @@ fun getContextElement(elementAt: PsiElement?): PsiElement? {
             ?.let { return it }
     }
 
-    return containingFile
+    return null
+}
+
+private fun getElementSkippingWhitespaces(elementAt: PsiElement): PsiElement {
+    if (elementAt is PsiWhiteSpace || elementAt is PsiComment) {
+        val newElement = PsiTreeUtil.skipSiblingsForward(elementAt, PsiWhiteSpace::class.java, PsiComment::class.java)
+        if (newElement != null) {
+            return newElement
+        }
+    }
+
+    return elementAt
 }
\ No newline at end of file
diff --git a/idea/testData/checker/codeFragments/anonymousObject.kt b/idea/testData/checker/codeFragments/anonymousObject.kt
index 359571355df..cb5d9422162 100644
--- a/idea/testData/checker/codeFragments/anonymousObject.kt
+++ b/idea/testData/checker/codeFragments/anonymousObject.kt
@@ -1,5 +1,5 @@
 val global = 2
 
 fun makeFace() = object : ObjectFace {
-    val inObject = 1
-<caret>}
\ No newline at end of file
+    <caret>val inObject = 1
+}
\ No newline at end of file
diff --git a/idea/testData/debugger/tinyApp/src/evaluate/singleBreakpoint/kt15259.kt b/idea/testData/debugger/tinyApp/src/evaluate/singleBreakpoint/kt15259.kt
new file mode 100644
index 00000000000..5319a43b206
--- /dev/null
+++ b/idea/testData/debugger/tinyApp/src/evaluate/singleBreakpoint/kt15259.kt
@@ -0,0 +1,14 @@
+package kt15259
+
+interface ObjectFace
+
+private fun makeFace() = object : ObjectFace {
+//Breakpoint!
+}
+
+fun main() {
+    makeFace()
+}
+
+// EXPRESSION: this
+// RESULT: 'this' is not defined in this context
\ No newline at end of file
diff --git a/idea/testData/debugger/tinyApp/src/evaluate/singleBreakpoint/kt15259.out b/idea/testData/debugger/tinyApp/src/evaluate/singleBreakpoint/kt15259.out
new file mode 100644
index 00000000000..a5126d6f8da
--- /dev/null
+++ b/idea/testData/debugger/tinyApp/src/evaluate/singleBreakpoint/kt15259.out
@@ -0,0 +1,7 @@
+LineBreakpoint created at kt15259.kt:7
+Run Java
+Connected to the target VM
+kt15259.kt:7
+Disconnected from the target VM
+
+Process finished with exit code 0
diff --git a/idea/tests/org/jetbrains/kotlin/idea/debugger/evaluate/KotlinEvaluateExpressionTestGenerated.java b/idea/tests/org/jetbrains/kotlin/idea/debugger/evaluate/KotlinEvaluateExpressionTestGenerated.java
index 24672eb8db9..d7848696b6a 100644
--- a/idea/tests/org/jetbrains/kotlin/idea/debugger/evaluate/KotlinEvaluateExpressionTestGenerated.java
+++ b/idea/tests/org/jetbrains/kotlin/idea/debugger/evaluate/KotlinEvaluateExpressionTestGenerated.java
@@ -256,6 +256,11 @@ public class KotlinEvaluateExpressionTestGenerated extends AbstractKotlinEvaluat
             runTest("idea/testData/debugger/tinyApp/src/evaluate/singleBreakpoint/kt12206BasePropertyWithoutBackingField.kt");
         }
 
+        @TestMetadata("kt15259.kt")
+        public void testKt15259() throws Exception {
+            runTest("idea/testData/debugger/tinyApp/src/evaluate/singleBreakpoint/kt15259.kt");
+        }
+
         @TestMetadata("kt17514.kt")
         public void testKt17514() throws Exception {
             runTest("idea/testData/debugger/tinyApp/src/evaluate/singleBreakpoint/kt17514.kt");