diff --git a/python/python-psi-impl/src/com/jetbrains/python/codeInsight/ConditionUtil.kt b/python/python-psi-impl/src/com/jetbrains/python/codeInsight/ConditionUtil.kt
index 280e588c019b..f2c5a2e0cad7 100644
--- a/python/python-psi-impl/src/com/jetbrains/python/codeInsight/ConditionUtil.kt
+++ b/python/python-psi-impl/src/com/jetbrains/python/codeInsight/ConditionUtil.kt
@@ -207,7 +207,7 @@ private fun getInvertedConditionExpression(
     val chainedExpressions = mutableListOf<PyExpression>()
     var currentExpression = expression
     while (currentExpression is PyBinaryExpression && comparisonStrings.containsKey(currentExpression.operator)) {
-      val leftExpression = (currentExpression.leftExpression as? PyBinaryExpression)?.rightExpression
+      val leftExpression = (currentExpression.leftExpression as? PyBinaryExpression)?.takeIf { comparisonStrings.containsKey(it.operator) }?.rightExpression
                            ?: currentExpression.leftExpression
       val invertedOperator = invertedComparisons.getValue(currentExpression.operator)
       val invertedExpression = generator.createBinaryExpression(
diff --git a/python/testData/intentions/PyInvertIfConditionIntentionTest/nonChainableBinaryExpressionAsComparisonLeftOperand.py b/python/testData/intentions/PyInvertIfConditionIntentionTest/nonChainableBinaryExpressionAsComparisonLeftOperand.py
new file mode 100644
index 000000000000..b4bf577553f4
--- /dev/null
+++ b/python/testData/intentions/PyInvertIfConditionIntentionTest/nonChainableBinaryExpressionAsComparisonLeftOperand.py
@@ -0,0 +1,3 @@
+def func():
+    <caret>if 4 - 3 == 1:
+        print("hi")
\ No newline at end of file
diff --git a/python/testData/intentions/PyInvertIfConditionIntentionTest/nonChainableBinaryExpressionAsComparisonLeftOperand_after.py b/python/testData/intentions/PyInvertIfConditionIntentionTest/nonChainableBinaryExpressionAsComparisonLeftOperand_after.py
new file mode 100644
index 000000000000..908007372615
--- /dev/null
+++ b/python/testData/intentions/PyInvertIfConditionIntentionTest/nonChainableBinaryExpressionAsComparisonLeftOperand_after.py
@@ -0,0 +1,4 @@
+def func():
+    if 4 - 3 != 1:
+        return
+    print("hi")
\ No newline at end of file
diff --git a/python/testSrc/com/jetbrains/python/intentions/PyInvertIfConditionIntentionTest.kt b/python/testSrc/com/jetbrains/python/intentions/PyInvertIfConditionIntentionTest.kt
index 761157eabdc2..c1de38ffd826 100644
--- a/python/testSrc/com/jetbrains/python/intentions/PyInvertIfConditionIntentionTest.kt
+++ b/python/testSrc/com/jetbrains/python/intentions/PyInvertIfConditionIntentionTest.kt
@@ -495,6 +495,11 @@ class PyInvertIfConditionIntentionTest : PyIntentionTestCase() {
     doTest()
   }
 
+  // PY-63319
+  fun testNonChainableBinaryExpressionAsComparisonLeftOperand() {
+    doTest()
+  }
+
   private fun doTest() {
     doIntentionTest(PyPsiBundle.message("INTN.invert.if.condition"))
   }